The Ultimate Guide To Button Down Shirts

If there’s one shirt a guy should have in his wardrobe, it’s a button down. Hands down, the button down shirt is one of the most essential and versatile pieces a man can own. Having a few of these in your closet can help complete your wardrobe. They are the perfect middle ground between a t-shirt and a dress shirt, allowing you to look put-together, stylish and relaxed all at the same time. Don’t forget to select your height and body type to filter the information applicable to you!

In this guide we’ll cover the 80/20 of button downs, giving you the information you need to rock these with confidence.

Feel free to read it in order or check out the table of contents to jump to sections.

TL;DR:

• Is different from a dress shirt
• Can be worn tucked or untucked
• Can be worn with jeans, chinos, khakis, shorts, and slacks
• Roll up sleeves for a relaxed look
• A tailor can help you get the perfect fit
• Use prints, patterns, and colors to make your body look bigger or slimmer
• If wrinkles and ironing are your kryptonite, go for wool shirts
• Roll your shirt when packing for travel
• Try different brands and fits to find “your brand”
• Measure yourself or your favorite shirt for more precise online shopping
• Makes a great shirt for dates, weekend, work and fun

WHAT IS A BUTTON DOWN

A “button down” shirt is referred to a long or short sleeve shirt with buttons going down the front and sometimes on the collar. Button downs can also be referred to as a “sports shirt” or “casual shirt”.

DRESS SHIRT VS BUTTON DOWN

They may look alike, but a button down is different from a dress shirt. Dress shirts are meant to be more formal and are typically worn with suits or dress pants, while button downs can easily be dressed up or down. The biggest difference is button downs can be worn untucked or tucked, where as a dress shirt must always be tucked in.

There are 4 ways to tell the difference between a dress shirt and a button down:

SIZING

Button down sizes are written as XS, S, M, L, and XL on the tag. However, dress shirts come in a numerical neck (i.e. 17) and arm length (i.e. 34/35) written as: 17 34/35. This is one of the easiest ways to know if the shirt you have is a button down or dress shirt.

LENGTH

Button downs are cut shorter so you have the choice to tuck or not tuck them. However, dress shirts are made extra long because they are meant to always be tucked in. So, if the shirt is going past your zipper and creeping into thigh territory, it’s probably a dress shirt. We’ll talk about button down length below and what you can do if your button down is simply just too long.

FOLDED VS HUNG

Button downs are usually found on hangers in the casual clothing section (i.e. next to jeans). Alternately, dress shirt usually come pre-folded with pins and clips to keep it in place and are placed near suiting and ties. Dress shirts can come hung, it just depends on the retailer.

FABRIC

The fabric on the collar and cuffs in button downs are the same throughout the shirt. With dress shirts the fabric, especially around the wrist cuff and collar, tends to be a bit stiffer for a more formal look.

BUTTON UP VS BUTTON DOWN

You might have heard the words “button up” and “button down” used in reference to these shirts. There is actually a very small difference between a button “up” and “down”, which is button “downs” have little buttons on the end of the collar, where as a button “up” doesn’t.

So what’s the point of the little buttons? They were initially meant for polo players so their collars wouldn’t go flying in different directions when playing. The benefits of the little buttons to the modern man? They keep the collar intact.

Buttons or no buttons? Shirts without the buttons can look slightly more dressy, other than that, it’s a personal preference thing.

HOW TO WEAR IT

TUCKED VS UNTUCKED

When deciding how to wear a button down, the age old questions comes up: to tuck or not to tuck? The answer: it depends on the occasion and what vibe you’re looking to give off.

WHEN TO TUCK IT IN

Anywhere you need to look dressed up, sharp, or professional – tuck in your shirt.

What are these settings? Think: dinner date at a nice restaurant, job interview, networking, wedding rehearsal dinner, or symphony. Also, if you’re planning on wearing something over your shirt like a blazer or sweater and want to look sharp, tuck it in.

WHEN TO UNTUCK IT

Go untucked when you want to look relaxed. Think: bars, park day, coffee shop, running errands, house parties, or a casual date. If you highly prefer going untucked most of the time, that’s totally fine because the modern man style allows you to do so and still look on point. Keep in mind, if you feel like tucking in your shirt for casual occasions, you definitely can.

You can pair your untucked shirt with a blazer, casual jacket or sweater, but keep in mind this look is in “relaxed” territory. If you want to wear your untucked shirt with a blazer, make sure there is no or very minimal amount of shirt showing in the back. However, if your shirt is longer than your sweater or casual jacket (i.e. bomber jacket), it’s fine.

All in all, if you want to give off a classic and sophisticated vibe, go for the tuck. If you want to give off a more chill and relaxed vibe, go untucked. Can you give off a chill vibe with a tucked in shirt? Of course, just roll up your sleeves and keep the top button undone.

UNTUCKED LENGTH

A little too often guys wear their untucked shirts too long. Here’s a rule of thumb: the shirt should fall anywhere between the middle and just above the bottom of your zipper. The closer to the middle of the zipper, the better.

Keep your shirt length within the white lines

The white lines indicate the “safe zone” of how long or short your button down should be. Anything above is too high and anything below is too long. Wearing your shirt near the middle of your zipper will make your legs look longer and make you appear taller.

On the other hand, button downs that are too long will make your torso look disproportionately long and your legs look shorter. If your button down covers your whole zipper, it’s too long.

Button down is too long

Tip: If you are on the shorter side, you want to stay near the top of the white line in the example above. Finding a shirt off the rack that hits this length will be tough, so it’s important to get a tailor to shorten the shirt for you. Trust me, the extra $15-20 is worth it. If you’re open with your budget, going custom-made isn’t a bad option. Custom shirts can start at $75, but high quality ones can start at $130.

Source: The Modest Man

This is the perfect length for guys on the shorter side

Tucking in your shirt will also make you appear taller. If you are wearing a belt, make sure it’s not too thick and isn’t the opposite color of your pants. You don’t want any obvious breaks in your body, this will make you appear shorter since the eye gets distracted when looking from top to bottom.

Source: The Modest Man

Belt doesn’t stand out too much, making legs appear longer

Tip: If you are 6’3 and above, you can go untucked or tucked. The important thing is to make sure your shirt is long enough, especially in the arms. You may need to look into “tall” sizes or brands that cater to taller men.

Dutch, Scandinavian, German and some American brands cater to longer lengths, while still keeping their shirts slim and modern. If a shirt fits you in the shoulders and arms, but feels a bit baggy around the waist, get a tailor to take in the shirt for you. Tailors can do amazing things in terms of fit with off the rack shirts and it costs around $20-$30. If you’re open with your budget, going custom-made isn’t a bad option. Custom shirts start at $75, but high quality ones can start at $130.

Oval Body Type Tip:

Wearing a tucked shirt as an oval man works really well because it shapes you better, makes your legs look longer and creates a break via the belt line. It’s important to wear your pants at the right level, which is about an inch below the bellybutton.

If you’re an untucked kind of guy, make sure the shirt fits well and the length falls in the middle of the zipper. It’s important to create an illusion of your legs being longer than your upper body.

ROLLING UP SLEEVES

There are two easy ways to roll up your sleeves: (1) the Casual Roll or (2) the Italian Roll.

THE CASUAL ROLL

1. Unbutton both buttons
2. Fold the cuff over
3. Tuck the cuff and roll it under so that the cuff creates a clean end of the sleeve
4. Repeat until desired length is achieved

Source: Esquire

Casual Roll

THE ITALIAN ROLL

1. Both cuff buttons should be unbuttoned
2. Fold the sleeve up, it should be an inch or so past your elbow
3. Fold the sleeve up just below the end of the cuff. A third of the cuff should be visible.

Source: Esquire

Italian Roll

If you’re new to rolling, practice rolling when you are not wearing the shirt.

WHICH ROLL TO GO FOR

All things even, your roll style is a personal preference. The Casual is simple, clean and easy, while the Italian can be a little more complex. However, if the inside of your button down cuff has a print and you want to show it, the Italian Roll is perfect for that.

Source: Hello His

Example of Italian roll with inside cuff print

HOW HIGH TO ROLL

You can go from a simple single roll to all the way up to your elbow. The higher up you go, the more casual it will look. However, don’t go past the elbow or it will look awkward. Let’s go over some example lengths:

Excited to show off that new watch? Try folding your sleeves anywhere in the forearm area, which is about 2 to 3 rolls. This is a nice length to keep it clean and classic, and also works for business casual.

Note : If you have very slim forearms and are self-conscious about them, don’t go too high in your roll. Refer to the example above on the left.

ROLLING HALF SLEEVE BUTTON DOWNS

You can fold your half sleeve button down shirt once or twice, depending on how long your sleeves are. Fold at the cuff and fold once more or twice more.

FIT MAKES A DIFFERENCE

If your button down sleeves are really baggy, wide or sticking out, that means the fit is off. Trying to fold an ill-fitted half sleeve button down will make it look like you have wings. Red Bull anyone?

Bad fitting half sleeve button down

AVOID THE FOLLOWING Rolls:

UNDOING BUTTONS

Undoing the top button gives off a relaxed vibe, while keeping all the buttons done up can be a stylish statement. If you’re new at this, keep your shirt either buttoned all the way up or leave the very top button unbuttoned. If you’re an undershirt guy, opt for a v-neck when unbuttoning.

If you want to keep it even more relaxed, unbutton the top 2 buttons. If you want to undo 2 buttons, either don’t wear an undershirt or wear one with a deep V.

Source: Pinterest

Top two buttons undone

Note : If you have a short neck, unbuttoning will help elongate it.

THE UNBUTTONED LOOK

Wearing an unbuttoned shirt with a t-shirt is a specific casual look that has an element of hip. This look is best with sneakers, boots or casual shoes since it’s meant to give off a relaxed weekend vibe. You can pair this look with jeans, chinos or shorts.

Curious to give this look a try? Here are some sample outfits for inspiration:

Triangle Body Shape Tip: The open shirt look creates vertical panels that make the upper body look slimmer, which will help balance it out with your lower body. If you’re a fan of horizontal striped t-shirts, you can pair it with this look as it won’t make you appear too wide.

Inverted Triangle Body Shape Tip: The open shirt look creates vertical panels that make the upper body look slimmer, which will help balance it out with your lower body. If you’re a fan of horizontal striped t-shirts, pair it with this look without making your body look too wide.

Oval Tip: The open shirt look creates vertical panels that make the upper body look slimmer, which will help balance it out with your lower body. If you’re a fan of horizontal striped t-shirts, pair it with this look without making your body look too wide.

Rectangle Body Shape Tip: Wearing an open shirt look will visually create vertical panels and make you look slimmer than you are. However, if you like the look, try layering it with a vest or jacket to add bulk.

POCKETS

The more pockets that you have on your shirt, the more casual it becomes. Other than that, pockets or no pockets is a personal preference.

NO POCKETS

No pockets offers a clean and dressy look. You can easily tuck this shirt in and wear it with a tie and slacks.

ONE POCKET

One pocket is convenient, especially for storing sunglasses. Depending on how the rest of the shirt looks, the pocket can add a touch of casual to the look. Going for smaller patterns or solids with a pocket can keep it on the dressy side of things, especially if you wanted to tuck it in. Having a button on your pocket makes it casual.

TWO POCKETS

Double pockets make a shirt casual. You would not wear this to any place you need to “dress up”.

Note : Double pockets are a great trick for hiding “man boobs”. Also, they can visually add bulk to your chest.

Inverted Triangle Tip: Double breasted pockets will make your chest look bigger. If you already have a big chest, especially compared to your waist, avoid. Single or no pockets work just fine.

Triangle Tip: If your shoulders slope, double check to see if the pockets land in the right place, if they don’t, avoid.

 Short King Tip: Avoid unnecessary details on shirts like double breasted pockets or pockets that stand out as they will make you look shorter. Other details include contrasting buttons (i.e. black shirt, white buttons) and giant logos.

A subtle pocket like the example below works great for guys on the shorter side because it doesn’t distract the eye and creates a smooth look.

A pocket with a subtle detail like the example below is okay because there is little distraction. However, if you want to appear taller, avoid any distractions.

Avoid a pocket that stands out like in the example below. Having added details like this distracts the eye when looking from top to bottom and breaks up the body.

TIES AND BUTTON DOWNS

Some nicer button downs can be pulled off with a tie. The biggest thing to watch out for is material and patterns. For example, solids are easy to pull of with a tie and some plaids too. I’ll go over some examples to make it easier to understand.

Wearing a button down and tie with a suit works for business and business casual settings. In the example below, the guy is wearing a plaid shirt that works really well with a tie and suit. However, if you need to be very formal, stick to a dress shirt.

Source: GQ

Example of plaid shirt with tie that works great

Note : If your button down has a busy print, go for a solid tie.

Avoid large and casual looking prints when trying to pair a button down with a tie. For example, the large box plaid in the example below screams casual, while the tie will try to make it look dressy, which is a recipe for confusion.

Don’t wear a tie with this style of casual pattern

Pairing your button down and tie with a sports coat keeps the look smart. You can easily dress up or down the looks with pants: jeans (casual, but nice), chinos (smart) and slacks (dressy).

Source: Indochino

Button down with tie and sport coat

If you are wearing a tie, tuck in your shirt and do up the top button. Your button down should be long enough to tuck into your pants without it coming out every time you raise your arms. Besides it looking very bad if it keeps coming out of your pants, it will be very annoying.

Source: I Am Galla

Button up with a tie

If your shirt looks too casual (i.e. has two pockets, is a very thick flannel, has too many button details, has an embroidered design on it etc.) a tie won’t look good and it will definitely throw off the look.

Avoid ties with shirts like this (ex: double pockets and flannel)

What about the untucked button down tie look? Honestly, don’t do it. It’s trying to be formal, but not. Basically, you’ll look like a young pop singer at an award show who’s trying to look “cool”. Avoid.

Source: Pinterest

Untucked shirt with a tie

WHAT TO WEAR IT WITH

What to wear with your button down can be broken down by Casual, Smart, and Dressy. You can mix and match the tops, bottoms, and shoes to make something casual look more dressy and vice versa.

A couple of notes:

• Avoid mixing casual shoes with the dressy category
• Jeans and dress shoes look fine as long as you mix the look with smart and dressy items
• Don’t mix shorts with boots or dress shoes

BOTTOMS

• Casual: Jeans or Shorts
• Smart: Chinos
• Dressy: Dress Pants or Slacks

MID-LAYER

• Casual: Sweatshirts, Hoodies
• Smart: Cardigan, Sweaters
• Dressy: Blazer

TOP LAYER

• Casual: Denim Jacket, Bomber Jacket, Parka
• Smart: Suede Jacket, Leather Jacket, Harrington Jacket, Quilted Jacket
• Dressy: Peacoat, Over coat

SHOES

• Casual: Sneakers, Street Shoes, Casual Boots
• Smart: Oxfords, Derby, Loafers, Nice Boots
• Dressy: Dress Shoes, Dressy Boots

Source: Pinterest

Style: Casual

Items: Button Down, Shorts (Casual), Slip-on Sneakers (Casual)

Stylist Note: This is as casual as you can get with a button down, but notice the look is still more stylish than shorts and a t-shirt.

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Source: Pinterest

Style: Casual and Modern

Items: Button Down, Shorts (Casual), Suede Derby Shoes (Smart)

Stylist Note: The shoes add a modern and stylish touch to an otherwise casual look – bonus points for hidden socks!

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Source: Pinterest

Style: Casual and Fun

Items: Button Down, Chinos (Smart), Sneakers (Casual)

Stylist Note: The chinos are rolled up at the bottom, making something smart look more casual and relaxed. The look is paired with a fun button down, making it weekend friendly.

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Source: Pinterest

Style: Casual and Rugged

Items: Button Down, Jeans (Casual), T-Shirt (Casual), Desert Boots (Smart)

Stylist Note: The flannel unbuttoned shirt gives the look a casual, but rugged vibe. The suede desert boots complete the look nicely, versus pairing it with a sneaker.

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Source: I Am Galla

Style: Casual and Modern

Items: Button Down, Chinos (Smart), Espadrilles Slip On Shoes (Casual)

Stylist Note: An otherwise very smart look is made stylishly casual with rolled up chinos and espadrille shoes, perfect for summer. A great example of how a look can easily be dressed up or down based just off shoes.

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Source: Pinterest

Style: Smart and Casual

Items: Button Down, Chinos (Smart), Boots (Smart)

Stylist Note: The shirt, grey chinos, and boots keep the look smart, while the rolled up sleeves and double pockets add the casual touch.

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Source: Notoriously Dapper

Style: Smart and Stylish

Items: Button Down, Chinos (Smart), Derby Shoes (Smart)

Stylist Note: A classic look gets a modern touch with rolled up chinos, smart shoes, no-show socks.

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Source: I Am Gala

Style: Casual and Modern

Items: Button Down, Jeans (Casual), Peacoat (Smart), Leather Sneaker (Casual)

Stylist Note: The Peacoat makes this look smart, while the leather sneakers keep it casual. Opting for a sleek leather sneaker versus a running shoe is an excellent choice for a modern look.

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Source: Pinterest

Style: Smart and Modern

Items: Button Down, Chinos (Smart), Coat (Smart), Vest (Casual), Chukka Boots (Smart)

Stylist Note: This otherwise very smart look is made modern with an untucked button down and Chukka Boots. Bonus points for added warmth with a down vest.

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Source: Pinterest

Style: Smart and Fun

Items: Button Down, Slacks (Dressy), Loafers (Smart)

Stylist Note: A fun tucked in button down is dressed up with slacks and a fashion forward loafer shoe. You can switch the shoe out for an oxford or derby if you prefer a more classic shoe.

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Source: Pinterest

Style: Dressy and Casual

Items: Button Down, Chinos (Smart), Blazer (Smart), Sneakers (Casual)

Stylist Note: An otherwise dressy look consisting of a blazer and chinos is made casual and modern with fresh white sneakers and a chambray button down.

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Source: Pinterest

Style: Smart and Modern

Items: Button Down, Jeans (Casual), Blazer (Smart), Oxford Boots (Smart)

Stylist Note: A tucked in button down, blazer and stylish Oxford boots pair perfectly well with a dark wash jean to keep this look modern and stylish.

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Source: Pinterest

Style: Smart and Classic

Items: Button Down, Slacks (Smart), Chelsea Boot (Dressy)

Stylist Note: A perfect example how to dress up your button down with slacks or dress pants for a professional look.

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Source: Pinterest

Style: Dressy and Fashion-Forward

Items: Button Down, Chinos (Smart), Blazer (Dressy) and Loafers (Smart)

Stylist Note: Creating a faux suit with a blazer and chinos is very smart and stylish look, which can easily be dressed up or down. In this example the look is slightly dressed down by unbuttoning the top two buttons.

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Source: Pinterest

Style: Dressy, Classic, and Smart

Items: Button Down, Chinos (Smart), Sweater (Smart), Tie (Smart), Blazer (Dressy), Shoes (Smart)

Stylist Note: This is high on the spectrum of looking dressy. The sweater, tie and button down paired with chinos and derby shoes give it a very professional look.

There you have it, all the ways you can make outfits with button downs. Keep in mind, you can easily switch out certain pieces like shoes or jackets to easily dress up or down a look. Use the examples above as a base and make edits to fit your style.

OVERALL FIT

FIT STYLES

One of the most important things you can do to dress well is wear clothes that fit properly. This means avoiding shirts that are too baggy or too tight. Luckily, brands make fits beyond Small, Medium and Large to help you achieve this.

Note : Each brand designs with a certain “fit model” in mind, this is why shirts can fit very differently from brand to brand. For example, some brands create very long shirts for taller guys, while others cut their arm holes high for slim guys. A fit model is a person (a model) the designer uses as their mannequin to make clothes for.

Common Fits:

• Classic Fit: Plenty of room through the chest and arms holes
• Regular / Tailor Fit: A little extra room through the chest and body, less tapered in the waist
• Slim Fit / Modern Fit: Fitted through the chest and arm holes, slightly tapered around waist
• Extra Slim Fit / Trim Fit: Slim throughout with higher arm holes.

Note : It’s important to make sure your shirt lines up well at the shoulders, most of the other stuff, like a loose waist, a tailor can fix.

Oval Body Type Tip: Men with an oval body shape should start off with a tailor/regular fit shirt then work their way up or down from there. In case it’s too big there are two options: 1) try on a slim fit and see how it works with your body 2) if the regular fit works better, get a tailor to make slight adjustments where you need them. Keep a look out for length, arm and back fit.

Rectangle Body Type Tip: Men with a rectangle body shape should start with trim fit then work their way up to a slim fit if needed. Remember, you don’t want your shirt to hug you because it will make you look slimmer. Instead, make sure it comfortably fits along your body.

Inverted Body Type Tip: Depending on how big you are, start with a slim fit and if it’s too snug, try going up one size before going to a regular fit. An important thing to note is you don’t want the shirt to be too snug around your waist because then your waist will look way too small compared to your shoulders.

Trapezoid Body Type Tip: Trapezoids should start off with a slim fit and then work their way up for down from there.

Triangle Body Type Tip: Triangles can fluctuate between slim fit and tailor fit, it just depends on the size of the hips and stomach. Start slim and work your way up.

Tall Guy Tip: Make sure the arm length fits you. You might have to go for “T” sizes or brands that cater to tall men.

GOOD FIT

SHOULDER

FIT NOTES

The shoulder seam should fall right at the edge of the shoulder. Going past the edge will make your shoulders look sloped. Going too high will make your shoulders look narrow.

COLLAR

The collar doesn’t need to be snug, but make sure there isn’t an obvious gap either. A sharp collar looks more professional, if your collar is weak, consider getting a collar stays.

Test: You should be able to comfortably fit two fingers inside your collar.

CHEST

The shirt should not pull at your chest nor should there be extra fabric hanging around the underarms.

Test: Sit down and see if the buttons pull. You can also raise your arms and make a triangle above your head to see if the chest pulls, however, the more important thing is to make sure it doesn’t pull when you are in a normal stance or sitting.

ARMS

The arms should not be frumpy, but don’t need to be tight at the same time. You should be able to bend your arm and not have the fabric pull.

Test: Raise your arm to the side and you shouldn’t be able to grab more than 1 to 2 inches of fabric right under your bicep.

WRIST

The length should fall past your wrist, right at the base of the hand.

Test: Flex your hand and you will see a dimple at your wrist near the thumb, your shirt cuff should end at this dimple.

WAIST

Make sure the shirt follows along your body and slightly shapes the waist. None of the buttons should pull, especially when you sit.

Test: Grab all the excess fabric around your waist to one side, you shouldn’t be able to grab more than 2 to 3 inches of fabric.

BACK

The back should lay flat. There shouldn’t be any fabric billowing out at the back. However, it shouldn’t be uncomfortably tight.

Test: Put your hands straight out in front of you and there shouldn’t be any uncomfortable pulling of fabric.

Note : Having extra fabric on the back can be common, your tailor can take in the sides or dart the back to make it flat.

LENGTH

The shirt should fall anywhere between the middle and bottom half of your zipper, the closer to the middle the better. The top your back pockets should be covered.

Test: Raise your hands in the air and create a triangle with your arms. Check to see if your stomach is exposed. If you’re a tucked in kind of guy, make sure the shirt doesn’t come out of your pants.

Note : Don’t assume every S, M, L is supposed to fit every male body type in the world. Finding a good tailor to make slight edits to your shirt is like getting a custom shirt.

HEM

One more thing to note is the hem of the shirt, which is the bottom of the shirt. There are two types:

ROUND HEM

A bit of a rounded hem is pretty standard in button downs and is the easiest to work with. If your hem is rounded and is showing the side of your belt loops, it’s too short.

Round Hem

FLAT HEM

A flat hem can be a little trickier. If you have a beer belly or are naturally round, avoid a flat hem as it can obstruct the otherwise straight bottom finish and make your stomach look bigger.

Flat or square hem

Note : If you love an old school 60’s clean cut look, a flat hem can help you achieve that.

And that, my friend, is how your perfect button down should fit. Now you might be thinking, “How is a button down supposed to fit me that well off the rack?” Never fear, I have a solution for you, which is your new best friend, the tailor.

TAILORING

Wait! Before you get rid of that shirt, there’s still some hope. Tailors can be your best friend when it comes to making sure your shirt fits you to the T! However, keep in mind that tailors can cut or take in fabric, but can’t add fabric. For example, they can easily shorten a shirt, but not lengthen it.

Note : Before taking your shirt to a tailor, make sure your shirt lines up well at your shoulders. This can be a hard part to fix, so it might not be worth the cost.

THINGS A TAILOR CAN FIX

• If your arms are too baggy, a tailor can tighten the arms. Price: $20-$30
• If your sleeves are too long, they can shorten them. Price: $20-30
• If the shirt is very big in the waist or back, a tailor can take in the sides. Price: $30
• If the shirt is slightly big in the waist or back, a tailor can dart the back. Price: $20
• If the shirt is too long, a tailor can shorten the hem. Price: $20
• If you don’t like the shape of the hem, a tailor can change it if there’s enough fabric: $20
• If your shoulders slope a tailor can take in the excess fabric bunching around the underarm: Pricing can vary depending on difficulty

Note : If you have sloping shoulders, wearing a blazer or jacket with your button down will help make your shoulders appear more broad.

Note : Once you find a good tailor you can trust, seek their opinion on whether a shirt fits well.

HOW TO FIND A GOOD TAILOR

• Check Yelp
• Most big department stores have in-house tailors
• Ask a men’s suiting store for a recommendation
• Ask a friend for a recommendation

Not sure if the price is right? Call a couple of spots and compare prices for the service you want. Bigger cities may charge more for services than smaller towns.

BAD FIT

One of the biggest style mistakes you can make is wearing an ill-fitted shirt. A fitted shirt can make you look more fit, tall and stylish, where as a bad fit will overwhelm you. If your shirt fits like the example below, you will look wider and shorter than you are.

Note : If it’s nearly impossible for you to find shirts that fit well, going custom-made might be the best option for you. Custom shirts start at $75 and up. Better quality shirts will start near $130.

PRINTS, PATTERNS AND COLORS

Aside from prints and patterns being aesthetically pleasing, they can help make our bodies appear bigger or smaller than they are. When deciding what pattern is best for you, the main thing to consider is creating balance with the upper body and lower body. For example, if you have a larger upper body and a slimmer lower body, going for a shirt with vertical stripes will help even you out.

Keep in mind that this guidance is a great stepping stone for those of you who are new to the style game. Once you get comfortable and confident with your clothes, feel free to start experimenting with different prints, patterns and lengths to see how they make you feel. This advice is to help you better understand why something might look good on you vs why it might not and what to watch for.

LIGHT COLOR SHIRTS

Light colored shirts are an easy staple to keep in your wardrobe. They are very versatile and can pair with numerous bottoms. If a bold white shirt isn’t your thing, try lighter shades of any color such as blue or grey to achieve a similar effect.

Light Shirts:

• Makes you look bigger
• When paired with light bottoms, streamlines the body and makes you look taller
• When paired with dark bottoms, breaks up the body and makes you appear shorter
• Great for daytime wear
• Offers a crisp, clean and classic look
• If your legs are way slimmer than your upper body, avoid really dark pants with light shirts

Note : Want to appear taller for that first date? Wearing monochromatic colors, like a light grey shirt and medium grey jeans, makes your body appear taller.

Rectangle Body Type Tip: Going for bright and light colored shirts will add visual weight to the top half of your body. This will make you appear bigger than you are, which is great for you.

Oval Body Type Tip: Wearing light colored shirts will make your upper body appear larger than it is. If you don’t want this, pair your light shirt with a jacket, blazer or sweater, which will slim the upper body. If you really love light shirts on their own, go lighter in the pants to make your legs appear wider too and create balance.

Trapezoid Body Type Tip: Lighter shirts add visual volume to the body, which is nice if you want your upper body to appear bigger than it is.

Triangle Body Type Tip: Wearing light colors will make your upper body appear larger than it is and exaggerate the stomach. However, pairing a light shirt with a jacket, blazer, sweater or even a tie can make the upper body appear slimmer. If you really love bright shirts on their own, go lighter in the pants to make your legs appear wider and create balance.

Inverted Triangle Body Type Tip: Wearing light colored shirts will make your upper body appear larger than it is. If there is already a big difference between your upper and lower body, don’t pair your light shirt with slim dark pants since your legs will look skinnier compared to your upper body. However, pairing a light shirt with a jacket, blazer, sweater or a tie can make your upper body not appear as large.

DARK COLOR SHIRTS

It’s a good idea to keep a couple of darker shirts on hand, especially for going out at night. Medium to dark colors doesn’t mean wear navy blue or black all the time. Instead, stick to medium to darker shades of your favorite colors like “olive” in the green family or “burgundy” in the red family.

Dark Shirts:

• Makes you look slimmer
• When paired with dark bottoms, makes you look taller
• When paired with light bottoms, makes you appear shorter
• Great for going out at night
• Offers a sleek and stylish look

Note : Not having a color major color break in your clothes can make you appear taller (i.e. pairing a navy blue shirt with black jeans and black boots)

Rectangle Body Type Tip: Medium to dark colors make your body appear slimmer than it is, if you don’t want to look any slimmer, it’s best to stick to lighter colors.

Oval Body Type Tip: Medium to dark colors make the body appear slimmer than it is, so they are great for balancing out the upper body with the lower body.

Trapezoid Body Type Tip: The darker the shirt, the slimmer the body looks. If you want to appear bigger than you are, go for medium to light shirts.

Triangle Body Type Tip: Medium to dark colors can help hide the stomach, so this works well if you want to look slimmer.

Inverted Triangle Body Type Tip: Darker colors make the body appear slimmer than it is, so if your upper body is much bigger than your lower body, medium to dark colored shirts can help balance out your body.

HORIZONTAL STRIPES

Horizontal stripes are pretty classic when it comes to prints. You don’t have to only go for horizontal stripes, but can go for a pattern that has prominent horizontal stripes to achieve the same effect like in the example below on the left.

Horizontal Stripes:

• Makes your body appear wider
• Can make you appear shorter
• The bolder the stripe, the bigger the effect of looking wide

Note : The eye follows horizontal stripes side to side, which is why people appear wider when wearing horizontal stripes.

Short King Tip: Avoid horizontal stripes as they will make you appear shorter. However, if you absolutely love horizontal stripes, pair them with a jacket or blazer to break up the wideness. Wearing a jacket or blazer creates an illusion of a vertical panels that help lengthen the body.

Rectangle Body Type Tip: Horizontal stripes are great for guys on the slimmer side because they will make your upper body appear larger than it is.

Oval Body Type Tip: Avoid horizontal stripes because they will make you look bigger than you are, making your upper body much larger than your lower body. However, if you absolutely love horizontal stripes, pairing your shirt with a jacket, blazer or sweater can help create an illusion of vertical panels, and slim you out on top.

Trapezoid Body Type Tip: If you want to appear bigger than you are, horizontal stripes will do the trick.

Triangle Body Type Tip: Avoid horizontal stripes because they will exaggerate your stomach. However, if you absolutely love horizontal stripes, pairing your shirt with a jacket, blazer or sweater can help create an illusion of vertical panels, and solve the issue.

Inverted Triangle Body Type Tip: If you want to appear larger at the top, horizontal stripes will help you achieve that. However, if your upper body is already much bigger than your lower body, horizontal stripes will exaggerate it and you will look disproportionate. If you already own horizontal stripes, pair them with a jacket to break up the stripes.

HORIZONTAL STRIPES ACROSS THE CHEST

Stripes just across the chest is a fun way to wear horizontal stripes without worrying about appearing wide or short.

Stripes Across Chest:

• Make your chest appear wider
• Creates an illusion of a taper from chest to waist

Rectangle Body Type Tip: Wearing stripes just across your chest is a great way to visually create a V shape from your shoulders to your waist. This is a great technique for rectangles who have straight bodies and want more shape. You can also go for a light shirt with stripes across the chest to make you look bigger, but still have the taper effect.

Oval Body Type Tip: Having horizontal stripes just across the chest while the rest of the shirt is dark will broaden your chest and slim your waist, giving an illusion of a V shape.

Trapezoid Body Type Tip: Wearing stripes just across your chest can exaggerate your V shape from your shoulders to your waist by making your chest look wider.

Triangle Body Type Tip: Since Triangles have a narrow chest and shoulders compared to the waist, the stripes across the chest are a great way to broaden up the chest. If you want to draw attention away from your stomach, stick to a darker base color.

Inverted Triangle Body Type Tip: Keep in mind stripes just across the chest will make your chest appear much larger, so if your chest is already much larger than your waist, it will exaggerate the difference and make you look disproportionate.

VERTICAL STRIPES

Vertical stripes are pretty classic and can easily be dressed up when tucked in and worn with dress pants or chinos.

Vertical Stripes:

• Make your body appear longer
• Make your body appear slimmer
• The bolder the stripe, the more the elongating effect
• Can easily be dressed up with chinos or slacks

Note : Vertical stripes can create the illusion of the body looking taller and slimmer because the eye follows the lines up and down.

Short King Tip: Vertical stripes will make you appear taller, however, don’t go for too thick a stripe. Photo #1 is the thickest you should go, anything more can make you look smaller by being too bold.

Rectangle Body Type Tip: Vertical stripes will make the rectangle body appear slimmer than it is, it’s best to avoid if you don’t want this.

Oval Body Type Tip: Vertical stripes are great for slimming out the upper body so it can look more balanced with the lower body. They are a great way to incorporate light colors into your wardrobe without having to worry about your upper body look too big.

Trapezoid Body Type  Tip: Vertical stripes are great for appearing taller.

Triangle Body Type Tip: Vertical stripes work well for triangles as they slim out the waist and some of the hip. They are a great way to incorporate light colors into your wardrobe, while making you appear slimmer and taller.

Inverted Triangle Body Type Tip: Vertical stripes work well for guys whose upper body is much bigger than their lower body because they slightly slim up the top and create balance.

PRINTS

From classic to fun to bold, there are plenty of prints to pick from. Just like horizontal and vertical stripes affect the appearance of our bodies, the size and contrast of prints can also make our bodies appear larger or smaller than they are.

Let’s first start by defining some common types of prints:

HIGH CONTRAST PRINTS

High contrast prints are a fun way to stand out of the crowd. High contrast means the shirt’s base color and print color are opposite (i.e. black and white).

High Contrast Prints:

• Adds personality to your style
• The taller you are, the bigger print you can go for
• The shorter you are, the smaller print you should go for
• High contrast prints make the body appear bigger
• The bigger the print, the bigger it makes your body appear

Note : Medium sized prints with high contrast make good shirts to wear unbuttoned.

Tip: Small to medium sized prints are the best place to start, then work your way and see the effect it has on your upper-body. It’s best to avoid giant prints.

Tall Guy Tip: The taller you are, the larger the print you can go for. However, keep in mind big prints will make you look even bigger, so if you’re already really tall, avoid going too large if you don’t want that affect.

Short King Tip: Avoid large prints as they will make you look smaller. If you love contrasting patterns, go for not so busy ones (i.e. dots). Tucking in your shirt, wearing a jacket and going for a pant color similar to the base color of the shirt can help streamline the body.

Rectangle Body Type Tip: Prints with contrast add visual weight to the upper body, which works great for slim guys wanting to appear bigger.

Oval Body Type Tip: Prints with a lot of contrast will make Ovals appear bigger than they are, however, tucking in your shirt can help help slim you out. If you love prints with contrast, try wearing lighter pants to create balance between your upper and lower body or throw a jacket on. Choose a print size that works with your body, medium is the best place to start.

Trapezoid Body Type Tip: The higher the contrast and the larger the print, the wider your body will appear. However, take your height into consideration and don’t overwhelm yourself by going too large.

Triangle Body Type Tip: Prints with a lot of contrast will make Triangles appear wider than they are. It’s best to wear a jacket with your busy shirt so you don’t exaggerate the stomach. Also, don’t go too dark in the pants with your contrast top because your legs will look slimmer in comparison.

Tip: Prints with contrast will make the upper body appear larger than it is and exaggerate the difference between your upper and lower body. If you love prints with contrast, go lighter in the pants to make your legs appear bigger or throw a jacket on.

LOW CONTRAST PRINTS

Prints with less contrast is a great stepping stone for those entering the world of patterns since they’re more subtle. Low contrast is when the base color and print color are similar (i.e. light blue and medium blue).

Low Contrast Prints:

• A subtle way to show personality
• The taller you are, the bigger print you can go for
• The shorter you are, the smaller print you should go for
• Low contrast prints make the body appear slimmer

Short King Tip: Stick to small and medium prints as large prints will make you look smaller.

Tall Guy Tip: Since low contrast prints are subtle, you can go for any size.

Rectangle Body Type Tip: Small prints with less contrast make the body appear slimmer than it is, however, medium to large prints will have less of the affect.

Oval Body Type Tip: Prints with less contrast will make the body appear slimmer than it is and will help balance out an Oval shape.

Trapezoid Body Type Tip: Prints with less contrast are easy to pull off for Trapezoids. The larger the print, the wider you will appear.

Triangle Body Type Tip: Prints with less contrast will make the body appear slimmer than it is and will help balance out the Triangle shape.

Inverted Triangle Body Type Tip: Prints with less contrast will make the body appear a slightly slimmer and can help balance out you out if your upper body is much larger than your lower body.

PLAID

Plaid is one of the most classic prints out there, but that also means it’s everywhere. However, there is a way to avoid looking like every other guy in the room, which is by playing around with different sizes and prints of plaid.

Each style of plaid can create an illusion of appearing wider, slimmer, taller, shorter etc. Let’s look at a few and see what effects they create:

Tip: The larger the print and the higher the contrast, the larger you will look.

Short King Tip: The shorter you are, the smaller you should keep the plaid. Large prints will make your body look small.

Rectangle Body Type Tip: Plaid with a lot of contrast and medium sized print will make your body look bigger. Best styles for you: Ex 1, 3, 4, 5, 8

Oval Body Type Tip: Plaid with small to medium sized prints with less contrast are the best for you. Best styles: Example 2, 6, 7. You could pull off Examples 3, 4 with a jacket. Don’t go too large with your plaid.

Trapezoid Body Type Tip: Trapezoids can pull off most plaid prints. The taller you are, the bigger plaid you can go for. Best styles for you: Ex 2, 3, 4, 5, 6, 7

Triangle Body Type Tip: Plaid with small to medium sized prints with less contrast are the best for you. Best styles: Example 2, 6, 7. You could pull off Examples 3 and 4 with a jacket.

Inverted Triangle Body Type Tip: If you upper body is much larger than your lower, plaid with small to medium sized prints with less contrast are the best for you, examples: 2, 6, 7. However, if your difference isn’t that big, you can pull of example 4.

FABRICS

Your choice of fabric can vary depending on the time of the year and how formal the occasion. I’m not going to bore you with a complete lesson in fabrics, but here’s a summary of what you actually need to know:

COTTON

Cotton shirts are pretty common. They can be lightweight and breathable depending on the fabric weight. The lighter the weight, the thinner the shirt, the more breathable it is. If you want extra comfort, go for a cotton shirt with stretch.

Subcategories of cotton:

• Washed cotton: more casual looking
• Fine cotton: dressed up
• Italian cotton: even more dressed up
• Oxford cotton: much thicker cotton (also known as a Oxford Cotton Button Down, OCBD)
  
  

Oxford cloth shirt

Best for: Year round

LINEN

Linen shirts are very breathable and are perfect for hot and humid environments. They have a tendency to fit loosely and wrinkle easy. They are okay to wear wrinkled, but it’s important to note they do give off a casual vibe.

Best for: Summer or hot environments

CHAMBRAY

Chambray looks like a denim shirt and is often confused for one. However, Chambray is made out of a plain weave fabric that has a soft and light feel, unlike denim. Chambray is a great option for those who like the look of a denim shirt, but don’t want to wear a thick shirt.

Best for: Year round

DENIM

Exactly what you think: jeans in the shape of a shirt. You can find denim shirts in lightweight or heavy denim, as well as dark and light colors. They fall in the casual category and look great with black jeans.

Best for: Fall, Winter and Spring

FLANNEL

Flannel is a thick wool or cotton shirt that is very warm. Don’t be deterred by the lumberjack stereotype, you can find flannel in a non-plaid patterns.

Best for: Cold weather

WOOL

Wool button downs are best in class when it comes to fabric. They last a long time, won’t wrinkle easily, and don’t absorb odor. You might have heard of Merino wool, which is also a great breathable option, especially for those who sweat a lot.

Best for: Year round

CARE

Now that you’ve found “the one”, how do you care for it so you can live happily ever after?

WASHING

How often should you wash your shirts? Only when they are dirty. This can vary from person to person since some men sweat more than others. If your shirt starts to smell after one wear, that’s your answer. However, the less you wash it, the longer you can preserve it.

DRY CLEAN

If your shirt tag says “dry clean only”, obey it. If your shirt doesn’t say “dry clean only”, it’s optional. Dry cleaning is the easiest option for those who hate doing laundry and ironing.

LAUNDRY

If you don’t want your shirt to shrink even the slightest, avoid warm and hot water and wash it in cold water only.

Throwing your shirts in the dryer can also cause them to shrink, so avoid the dryer and dry them flat. The dryer in general has a tendency to weaken fabrics, so don’t go too hot if you can’t live without it.

Note : Unless the care label says otherwise, put fabric softener in your washing machine if you want to naturally dry your shirts. Fabric softener keeps them from feeling crunchy, especially when washing them in cold water.

WRINKLES AND IRONING

I hear it all the time…”I hate ironing shirts!” Unless you want to be limited to wrinkle-free shirts, which end up mostly being dress shirts, wrinkles are a part of life. But wait… what if I told you there is a magic wand that releases hot steam that you can wave over your shirt and it gets rid of wrinkles? It exists! It’s called a steamer. Get one! Here are a couple to check out: Handheld (good for traveling/takes up less space) or Full Size (easy and quick to use everyday).

While shopping you can keep a look out for shirts that say “wrinkle-free”, however, a majority of these shirts might be dress shirts, so make sure you’re getting a button down.

PACKING FOR TRAVEL

When packing a button down, roll up your shirt to maximize space in your suitcase and avoid heavy wrinkling. If you get a few wrinkles and don’t have access to an iron, hang the shirt in the bathroom while you shower, the steam from the shower can help get rid of some of those wrinkles.

Source: Ethan Man

SHOPPING NOTES

LOOK FOR STRETCH

If you love being comfortable and are new to the world of button downs, go for one with stretch. Tug the fabric to see if it stretches.

DON’T BE AFRAID TO TRY THINGS

Have fun with prints and textures. If you are new to button downs, feel free to start with plaids or solids and work your way up. If you’re ready to step it up a bit, try dots, woven textures, chambray, or novelty prints.

FIND YOUR BRANDS

Different brands fit in different ways and it’s helpful to find which ones are made for you. The easiest way to find yours is by trial and error. Source 4 to 6 different brands of shirts and try them in a change room to see how they fit. Keep a look out for “Slim Fit” or “Regular Fit” as well. Once you know which brands and fits work, it’ll be easier to add shirts to your wardrobe with minimal effort.

MEASURE

Either measure your body or your favorite shirt and compare the measurements listed online to see if they compare or are close. This is great for people who have trouble finding sleeves or lengths that fit. You will need a tape measurer for this.

Sleeve: Some sleeve measurements start from the base of the neck to the cuff, these measurements are usually in the 30s (i.e. 34). If the measurement is in the 20s (i.e. 26) that means it’s measureed from the shoulder seam to the cuff.

Shoulder: Measure from shoulder seam to shoulder seam.

Chest: Measure from underam to underarm.

Length: Measure from where the neck meets the shoulder (right next to the collar) to bottom of shirt.

FAQ

Some guys wear their shirts wrinkly, is that on purpose?

Cotton has a tendency to wrinkle easily, so it’s normal for shirts to wrinkle throughout the day. However, there are some brands, like J. Crew, that market the relaxed and naturally wrinkly look, which is a personal style preference. If you like the shirts, but not the wrinkly look, you can easily iron them.

Can I wear an undershirt with a button down?

You can definitely wear an undershirt with your button down. Not showing your undershirt is more stylish than showing it, so opt for a v-neck undershirt. If you heat up easily, look for breathable undershirts that have cooling technology. Also, wearing an undershirt can help with not having to wash your shirt after each wear because the undershirt can absorb the sweat and odor. It’s also okay not to wear an undershirt if that’s your personal preference.

My collar keeps flopping to the side, does that mean my shirt is done?

Overtime collars can get weak, but that doesn’t mean you need to toss your shirt. Consider getting a collar stay to make sure it looks crisp and sharp.

What’s up with denim/chambray button downs?

Denim button downs are a fashion forward look for guys who like a rugged style. They are meant to be worn casually and come in a number of thicknesses. You can pair them with colored jeans such as olive, burgundy, black or wear denim on denim. If you like the look, but aren’t into the denim shirt thing, try a chambray shirt. Chambray shirts have the denim look, but are much thinner and can be dressed up.

Denim on denim is a very specific look that some fashion forward guys like to wear. If it makes you cringe and all you think of is a Canadian tuxedo, avoid it. If you want to try it, wear opposite color denim at the top and bottom, for example a darker shirt and lighter jeans.

Source: Magic Fox

When wearing my button down with a sweater, should I go with a v-neck or crew neck sweater?

You could go either way depending on what look you like. The v-neck shows more neck, which is nice for guys with short necks. If you go for a crew neck, make sure the sweater isn’t right up against your neck or you will look uptight. Keep the very top button of your shirt undone, unless you need to be very formal. If you want to wear a tie, go for the v-neck.

Congrats, you made it to the end! You’re a button down expert now. If you have questions or feel like I missed addressing something, feel free to tell me in the comments. The next step is to check out the other guides. Chinos pair really well with button downs, so check that one out!

Guess What? I’m coming out with a men’s style course! Click here to learn more.