From Chukka to Chelsea, boots have become a staple piece in the modern man’s wardrobe. Whether you like to dress up or down, there is a boot out there for every occasion. Wearing a pair of boots with even the simplest outfit can elevate your style.

Photo Credit: Pinterest, Magic Fox, Pinterest

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

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Too Long; Didn’t Read

What Are Boots

From ankle to sole, there are many parts that help make up a boot’s form. Understanding boot construction is the best place to start since i’ll be using these terms throughout the guide.

Boot Collar: helps minimize irritation of the Achilles tendon and lower calf (depending on the height of the boot).

Hook Fastening: hooks you can put the laces into to further secure the boot.

Upper: literally the upper part of the boot. If you see a label that says “leather upper”, that’s the only part of the shoe that is leather.

Eyelets: the holes that the laces go through.

Stitch Down Construction: where the outsole and boot are sewn together. Stitch down indicates a good quality boot.

Tread: the bottom of the boot, which provides grip.

Insole: refers to the inside sole of the shoe – a good shoe will have a comfortable insole, while cheaper ones might not. However, you can always put your own insole into a boot.

Outsole: outside sole of shoe.

Tongue: the piece of fabric under the laces


Styles of Boots

Boots come in three styles: casual, smart and dressy. Casual boots are meant to be worn when you do not have to dress up at all (i.e. weekend). Smart refers to the Smart-Casual style, meaning these boots can be worn to work, on a date, or anywhere you want to make a good first impression. Dressy boots can be worn to more formal occasions or even with a suit, but are not limited to formal only outfits. I’ll point out these looks in the photos, so you can understand them better.

Casual Styles

Casual boot styles can be worn day to day and don’t offer a formal look to your outfits.

Work Boots

When you think of a work boot in the traditional sense, a steel toe boot might come to mind. However, the modern work boot is a day to day shoe that is perfect for the guy who likes to keep things on the casual side. Work boots are defined by their casual and bulkier style, especially in the toe area which can be reminiscent of the steel toe look. Some popular companies that specialize in work boots are Red Wings, Timberlands and Doc Martin’s, each having their own distinct style of a heavy duty work boot.

Doc Marten Boot

Red Wing Style Boot

Photo Credit: Nordstrom, Nordstrom

Timberland Boot

Classic Suede Work Boot

Photo Credit: Timberland, Nordstrom

Cap Toe Classic Work Boot

You can wear it hiking

Photo Credit: Pinterest, Pinterest

Looks great with casual clothing

Timberland work boot outfit

Photo Credit: Pinterest, Pinterest

Work boots look the best with casual clothing such as jeans and washed chinos. Avoid work boots for any dressy occasions or environments you need to look professional in.

Combat Boots

Classic Combat Boot

Photo Credit: Nordstrom

Rugged style boot

Clean and classic style boot

Photo Credit: Fashion Runway, Bedstu

Dressed up combat boot

Dressed down combat boot

Photo Credit: Pinterest, Thousand Yard Style

Note: If you go for a really minimal black combat boot, you can wear it formally

Combat boots are a style of boot that have more of a military look to them, hence the name. They are defined by their higher length and laces that go up to the very top. Combat boots come in rugged and sleek styles, which are perfect for the guy who wants a little edge in his looks. If the thought of repeatedly undoing and doing laces is already driving you crazy, opt for boots with a zipper on the inner side of the boot.

Hiking Boots

Day to day hiking boot

Photo Credit: Nordstrom

Although the first thought that comes to mind when you hear hiking boots is REI, or any other outdoor gear store, rest be assured there are hiking boot styles that work for day to day. Hiking boots can be defined by their soles because they have visible treads, thick laces, and hook like eyelets. Hiking boots work best with casual wear and are perfect for the guy who likes to dress for nature.

Photo Credit: Fashion Beans, Pinterest

Photo Credit: Bruno Cucinelli

Before you think Hiking boots are only for the very casual, they come in dressy version as well.

Dressed up hiking boot: great for winter

Photo Credit: GQ

If you have a very casual and outdoorsy style, modern hiking boots can be the ones for you. Keep in mind, they do fall in the casual category and should not be worn to any professional or formal occasion.

Smart Casual Styles

Smart Casual styles let you dress up or down your outfits depending on what look you are going for. Jeans make these boots look more casual, while chinos can add a dressier touch.

Apron or Moc Toe Boots

Moc Toe (or Moccasin Toe) boots, also called Apron toe boots, resemble a moccasin shoe with its square shaped toe cap. These boots can range from a casual style, usually with a white rubber outsole, to a smarter style with a wooden outsole. This style of boot looks best with jeans and chinos.

mens apron toe boots brown leather

Wooden outsole = dressed up boot

Photo Credit: McCaren and Sons

Photo Credit: Pinterest, Pinterest

Wooden Outsole = Dressy

Rubber outsole = casual

Photo Credit: J. Crew, Pinterest

Chukka or Desert Boots

The Chukka boot is the perfect starting point for someone wanting to get into the world of boots. They can easily be dressed up or down and go with everything from t-shirt and jeans to business attire. Chukkas are defined by a low eyelet count and ankle length. You might have heard the term “Desert Boot”, which is basically a Chukka, but with a rubber sole. Chukkas are good for dressing up, while a desert boot is good to keep things casual.

Classic Chukka Boot

Photo Credit: DSW

Desert Boot = rubber outsole

Chukka Boot = wooden outsole

Photo Credit: Idle Man, Pinterest

Photo Credit: Pinterest, Ashley Weston

Photo Credit: Pinterest, Pinterest

Chukka boots come in suede fabrics, which are great for a middle point between a leather chukka boot and a desert boot.

Dressy Styles

A classic dress boot can range from being very dressy to somewhat dressy depending on a couple of factors such as the finish, simplicity, and toe style. The more simple a boot, the dressier and more formal it looks. For example, going for a grainy leather finish can make the boot look slightly less formal, while going for a shiny leather finish makes it dressier. Also, a simple outsole can make it look more formal, while going for a contrast outsole (i.e. wood) can make it slightly less formal.

Plain Toe Boots

A plain toe boot doesn’t have a design at the front top of the boot.

Plain Toe = Nothing on the front toe

Plain toe dress boot with contrast sole

Photo Credit: Nordstrom, Allen Edmonds

Photo Credit: Thursday Boot, Pinterest

A simple boot makes it dressier

Photo Credit: Pinterest, Pinterest

Cap Toe Boots

Cap toe boots are defined by a line going across the front top of the boot. The cap toe can be a simple line or have a more decorative one known as “brogue”.

Cap Toe = Line across the front top

Photo Credit: J. Crew, Johnston & Murphy

Photo Credit: Pinterest, Pinterest

Photo Credit: Pinterest, Pinterest

Brogue Boots

If you like a little more going on in your shoe, a Brogue boot is a great choice. These boots are defined by their decorative perforations such as a wingtip, medallion or cap toe design at the front top of the boot. These boots fall on the dressier side of things and are perfect for suits or simply dressing up your jeans and button down outfit.

Cap Toe: There is a decorative line across the front top of the boot.

Brogue Cap Toe

Photo Credit: Nordstrom

Wing Tip: There is a wing like design on the front top of the boot.

Wing Tip

Photo Credit: Nordstrom

Medallion: There is a design at the top front of the boot. In the example below, you can see two toe styles can be combined, in this case cap toe and medallion.

Medallion + Cap Toe

Photo Credit: Nordstrom

Combination: Two or all three designs can be mixed together into one boot.

Medallion + Wing Tip

Photo Credit: DSW

Brogue boots look great with cuffed jeans

Photo Credit: ASOS, Pinterest

Chinos and brogue boots

This cuff is slightly high, could be lower

Photo Credit: Pinterest, Pinterest

Don’t know where to start? The “safest” place to start is with a plain toe boot because it can be dressed up or down without thinking too much about how the design works with the rest of your outfit. However, if you plan on having a couple of pairs of boots, it’s fun to experiment with different designs. Think of the design as the “bespoke” aspect of your outfit. Refer to the images above on how to best wear a wingtip boot.

Balmoral Boots

If you want a boot for suits and dressy occasions, a Balmoral boot is an excellent choice. The boot is defined by lacing up high at the ankle, hook closure and distinct stitching or contrast fabric between the upper and lower boot. Balmoral boots usually come with a cap toe or wing-tip design.

Balmoral boots have a distinct line that separates the upper

Photo Credit: Bodileys

Photo Credit: Pinterest, GQ

Photo Credit: Pinterest, Splash News

Chelsea Boots

Chelsea boots have a clean and simple toe, which allows them to easily be dressed up or worn with a “smart” look. The shiny leather boot versions do fall on the dressier side of things, but the suede version can be worn with something as simple as a t-shirt and jeans. Chelsea boots are defined by stretchy fabric on either side of the boot, which makes them easy to put on and take off.

Photo Credit: Nordstrom

Photo Credit: Pinterest, Fashion Gens

Photo Credit: Pinterest, Pinterest

Jodphur Boots

Jodhpur boots are a great choice for guys who like a clean boot, but also enjoy a Western vibe. Jodhpur boots are defined by their buckle that hits at the ankle.

Photo Credit: Heddels

Photo Credit: J. Fitzpatrick Footwear, @irvinrandle

Photo Credit: Pinterest, Pinterest

Monk Strap Boots

If you love the look of Monk Strap shoes, well guess what? They come in a boot version too! Monk Straps are defined by their double buckle and can come in everything from plain toe to brogue styles.

Photo Credit: Amazon

Photo Credit: Pinterest, Santoni

Photo Credit: Pinterest, Pinterest

Zipper Boots

If you hate the thought of constantly undoing and doing laces, a zipper boot might be the perfect match for you. Most of the boots I described above do come in zipper versions.

If your boots are lace up, the zipper will be hidden in the inside of the shoe. You do not have to untie your laces if you have a zipper.

Photo Credit: Frye

If you are going the zipper route, opt for a sleek pair of zipper boots rather than a bulkier one. The example below on the left shows a square and bulky style I recommend staying away because they look very old school. However, the example on the right is a better choice because it’s slimmer, has a nice wood accent, and the round-ish toe style is way more modern than a square toe.

Old School and dated

Sleek and modern

Photo Credit: Zappos, Johnstron & Murphy

What Style of Boot Should You Go For?

Alright, now that you know all the styles of boots, which one should you go for? Start by asking yourself if you prefer to dress casual, smart or dressy.


If your overall style preference is casual, it’s best to go for a work boot style shoe. Work boots keep up with your t-shirt and jeans look, but can also go with a button down for those days you want to look smart-casual.

Photo Credit: Pinterest, Pinterest

Smart Casual

If you want a boot that can work for dressy and casual occasions, Chukka boots are you go-to. You can wear them with a t-shirt and jeans or with something business casual.

Photo Credit: Cobble & Hyde, Pinterest


If you prefer an upscale look and find yourself dressing up more often than not, a Chelsea boot is a great starting point since they pair really well with dress pants and even dress up jeans. If the no-lace look isn’t your thing, go for plain toe dress boot with laces.

Photo Credit: @AlexanderLiang, Pinterest

If you like having a bit of flare in your style, go for a boot with a wing tip design. Wing-tip boots can work well with everything from a t-shirt and jeans to suits.

Photo Credit: Norris Dantaford

How To Wear Them

Boots are easy to pair with jeans, chinos and dress pants. If you want to elevate your look, there are small things you can do like cuffing your jeans that can help achieve that.

Jeans and Chinos

Pairing jeans and chinos with boots is an easy look, especially for first time boot wearers. Let’s go over a couple of tweaks you can make to appear more stylish.

Rolling and Cuffing with Boots

There are a couple ways to wear rolled pants with boots and it depends on your boot style. If you boots hit at the ankle, you can roll your pants up to the top of the boot.

Photo Credit: Pinterest, Pinterest

Photo Credit: Swagger New York, Pinterest

If your boot has a slim opening and goes above your ankle, you can roll your chinos to the middle or the top of your boot.

Photo Credit: Pinterest, Pinterest

You can also roll and tuck the front part of your chinos under the boot tongue.

Just front tucked, works with slim pants

Photo Credit: Pinterest

Over Your Boots

If your boots are slim at the ankle, you can wear your pants over your boots for a clean and classic look.

Photo Credit: Pinterest, Pinterest

The Half Tuck

If your boots have a tongue that sticks out (like in a desert boots), you can tuck the pants into the tongue and have the rest of the chino naturally fall to the sides and back.

Photo Credit: Pinterest, Pinterest

Photo Credit: Pinterest

The Full Tuck

You can tuck all of the bottom of your pants into your boots. Slim pants work better for this look. You can either fold the pant out and then tuck it in like the example on the left. You can also tuck them into your socks and let them naturally fall out as you walk like the example on the right.

Photo Credit: Pinterest, I Am Galla

Photo Credit: Pinterest, Pinterest

Dress Pants

When it comes to dress pants and suits, always wear your pants over your boots. Opt for dressier boots to keep up with the look. Your best options are: Balmoral, Brogue Boots, Plain Toe, Cap Toe, Jodphur Boots, Zipper Boots or Monk Strap Boots.

Photo Credit: Pinterest, D’Marge

Photo Credit: Pinterest

What to Wear With Boots

What to wear with your boots 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:

  • (1) Avoid boots in the casual or smart category with formal suits
  • (2) All boots can go with jeans, but stick to dressy boots for dress pants and chinos
  • Casual: Jeans or Shorts
  • Smart: Chinos
  • Dressy: Dress Pants or Slacks
  • Casual: T-shirt, Henley
  • Smart: Button Down Shirt, Polo
  • Dressy: Dress Shirt
  • Casual: Sweatshirts, Hoodies
  • Smart: Cardigan, Sweaters
  • Dressy: Blazer
  • Casual: Denim Jacket, Bomber Jacket, Parka
  • Smart: Suede Jacket, Leather Jacket, Harrington Jacket, Quilted Jacket
  • Dressy: Peacoat, Over coat

Example Outfits

Photo Credit: Pinterest

Style: Casual
Items: Boots; T-Shirt (Casual); Jean Jacket (Casual); Shorts (Casual)
Stylist Note: When it comes to wearing boots with shorts, it’s best to stick to a desert boot because of its low cut and casual style. Your socks should not show.

Photo Credit: Pinterest

Style: Casual
Items: Boots; T-Shirt (Casual); Jacket (Casual); Jeans (Casual)
Stylist Note: Boots can make even the simplest jeans and t-shirt outfit look stylish. Pair the look with a jacket, in this case a denim jacket, for the perfect layer. The contrasting colors on the boots look great.

Photo Credit: Sobatak

Style: Casual
Items: Boots; Button Down (Smart); Jacket (Casual); Jeans (Casual)
Stylist Note: A work boot with a button down and jeans can keep things on the casual side. Timberlands can still be considered stylish guys!

Photo Credit: Pinterest

Style: Rugged
Items: Boots; Sweater (Casual); Jacket (Casual); Jeans (Casual)
Stylist Note: Boots pair really well with leather jackets and help keep up the rugged look.

Photo Credit: Pinterest

Style: Smart Casual
Items: Boots; Sweater (Smart); Chinos (Smart);
Stylist Note: Chukka boots are a great alternative to dress shoes when you want to look business casual for work.

Photo Credit: Pinterest

Style: Smart Casual
Items: Boots; Button Down (Smart); Chinos (Smart);
Stylist Note: The suede desert boot adds the perfect casual touch to this look, but can easily be taken up to dressy-smart by wearing a leather boot.

Photo Credit: Pinterest

Style: Smart with hint of Bespoke
Items: Boots; Button Down (Smart); Vest (Dressy); Sweater (Smart); Jeans (Casual)
Stylist Note: If you like that classic bespoke style, boots are the perfect footwear to achieve that look.

Photo Credit: Pinterest

Style: Dressy
Items: Boots; Dress Shirt (Dressy); Blazer (Dressy); Jeans (Casual)
Stylist Note: Pairing your jeans and blazer with a sleek pair of Chelsea boots keeps up with the dressy side of things.

Photo Credit: Pinterest

Style: Business
Items: Boots; Dress Shirt (Dressy); Jacket (Casual); Slacks (Dressy); Tie (Dressy)
Stylist Note: Plain toe dress boots work well with slacks and a dress shirt. You can also pair this look with a brogue dress boot.Photo Credit:Pinterest

Photo Credit: GQ

Style: Dressy Casual
Items: Boots; T-Shirt (Casual); Suit (Dressy)
Stylist Note: Suits and boots go really well together and add a non-traditional element to the look. If you need to be formal, go for a plain toe or brogue boot. This look can easily be worn with a dress shirt and tie and still look amazing.

Photo Credit: Soletopia

Style: Dressy
Items: Boots; Dress Shirt (Dressy); Suit (Dressy)
Stylist Note: Wearing Chelsea boots with a suit keeps up with the formal look and is always a safe option if you are unsure what boots to pair with a suit.

Overall Fit

First and foremost, boots should be comfortable. The beauty of going for a good leather boot is it will stretch with your foot as you wear them.


Make sure there is no rubbing at the back of your ankle or leg. Eventually it will break the skin and you will bleed, which is no fun. Sometimes boots can do this at the beginning as this is the “breaking in” period. A temporary solution is to buy a cushioned band-aid and stick it in the irritating area.

Insole & Toe Cap

Photo Credit: Super Feet

Your foot should fit comfortably in the insole. It should not be able to move back and forth. However, make sure your toe isn’t up against the front of the shoe, there should be a little room. Do not buy boots that are too large because your foot and boot’s flex point should line up. The flex point is the curve in the middle of your foot at the bottom. If they do not line up, you can cause harm to your foot.

Make sure your toe isn’t hitting the top of the boot. That means the shoe is too small for you and you need to move up a size. You should have wiggle room. If you have wide feet, opt for a “W” size boot.

What a Cobbler Can Fix

Just like there is a tailor for your clothes, there’s a cobbler for your shoes. Here are some things they can fix for you:

  • Shoes too tight: A cobbler can stretch out your shoes. They have a machine at their workshop that can target a specific area to stretch. This includes a pinching toe, tight heel or tight calf.
  • Replace Sole: Whether you’re in need of a brand new sole or don’t like the one your current boot comes with, a cobbler can resole your boots. If you love your boots and they are a bit slippery at the bottom, a cobbler can put in a no-skid sole for you. Your soles must be resoleable, so it’s best to ask if they are when you buy your boots.
  • Uncomfortable Insole: a cobbler can add padding to your insole.
  • Smelly boots? Don’t need to toss them. A cobbler can professionally clean your boots inside and out. You can also get a spray for the inside of your boots, there are some good ones out there
  • Waterproof your boots: Alright, if you’ve ever lived in a rainy or snowy area, you know the feeling of wet socks. Well, a cobbler can protect your shoes from the elements!

What You Can Fix

There are certain things you can do at home to protect or refresh your boots.

  • Protect your boots with a leather and suede protector. The spray creates a protective barrier that will stop scratches or stains to sink into your boots. You can also buy waterproofing spray, but don’t expect it to get you through a torrential downpour for 5 hours.
  • Boots smell? Get a deodorizing spray to keep them lasting longer.
  • Add in your own insoles if the inside of your boot isn’t comfortable.
  • Stretch your boots with a leather stretching spray.

What to Look for in a Boot

When it comes to boots, there are a couple of things you should look for if you are “investing” in them. Details like types of leather and stitch down construction can help your boots last longer and make sure you get more bang for your buck. If you are not looking to “invest” in a pair of boots, look for comfort and style.

Types of Leather

Knowing what a “good” vs “bad” leather is will help you spend wiser. Keep in mind, i’m not telling you to spend a ridiculous amounts on boots, but what I am telling you is to make sure you’re not overpaying for something that isn’t as good.

Full Grain

Source: Leather Honey

Full grain leather is the best in class. If you see this on the boot, it’s a great sign. Not only is it the strongest and most durable leather, it ages well and resists moisture.

Top Grain

Source: Leather Honey

Top grain leather is a step below full grain leather. It’s not as durable because the top layer of the leather has been sanded down to make it look more uniform. However, it’s not a bad choice compared to some other leathers out there.

Bonded Leather

Source: Leather Honey

It’s exactly what it sounds like, leather scraps that are bonded together to create a sheet of leather. Although it’s technically real leather, it’s not as durable as full grain or top grain. Don’t spend a lot on these.

Genuine Leather

Source: Leather Honey

This term sounds amazing, but sorry guys, it doesn’t mean what you think it does. Genuine leather is made from the bottom cut, but doesn’t have any grain and is heavily processed. So yes it is leather, but it’s not good leather. You might be better off buying faux leather. Don’t spend a lot on these.

Corrected Grain Leather

Image result for full grain leather examples
Photo Credit: Ozapato

This leather can look fancy, but it’s actually low quality leather that has been printed with fake grain to make it look luxurious and real. Don’t spend a lot on these.


If you see a really cheap pair of “leather” boots, double check the label, they might be polyester. Polyester can look like real leather, but it’s a synthetic material. Make sure you don’t spend a lot on these.

Leather VS Suede


Suede and Leather are generally the same material, which is cow hide. However, Suede is the inside of the hide whereas leather is the outside of the hide. Suede can also come from sheep and pigs.

Image result for full grain leather
Photo Credit: Jackson Wayne Leather Goods

Dressy Factor

Suede and Leather are generally the same material, which is cow hide. However, Suede is the inside of the hide whereas leather is the outside of the hide. Suede can also come from sheep and pigs.



Photo Credit: Gant, Taft

Suede Dressed Up

Leather Dressed Up

Photo Credit: Pinterest, GQ

Note: An easy rule of thumb to remember is: if you are trying to be formal, go for a darker boot. Dark does not mean only go for black, but going for a dark brown, dark burgundy etc.

What’s Better?

If you’re looking for durability, you probably shouldn’t go for suede because it is more fragile and will get damaged when it comes in contact with water. However, if you are going for pure aesthetics, suede is pretty good looking! Suede might not be your day to day shoe, but it can definitely be a nice boot to have in your wardrobe.

Stitch Down Construction

Photo Credit: Truman Boot Company

See the white stitching? That’s stitch down construction. If your boot has this, excellent! It’s a marker of a good pair of boots. This stitching connects the upper boot to the sole of the boot. What’s neat about this style of stitching is it allows you to resole your boots if you need to, making them last for years on end. Other words used for stitching: Norwegian Welt or Goodyear. The alternative to stitching is a glued down sole, which as you can imagine, will eventually detach from the boot.


Photo Credit: Real Men Real Style

If you live in a place where there are cold and wet winters, having good treads on your boots is going to save you a lot of slips. You can always get a cobbler to add treads if your current pair doesn’t have them.


For your first pair of boots, go for either black or brown since they are a staple color to have. Black and brown boots are very neutral and go with everything.

Classic Colors

When buying your first pair of boots, go for classic colors like brown, black or grey.



I can safely say brown leather boots go with almost every outfit under the sun. Think of brown boots as a pop of color in your outfit. For example, if you’re wearing all dark colors (i.e. black t-shirt and dark blue jeans) a brown boot is great for breaking up the darkness and bring your outfit to life.

  • Brown boots work really well with neutral, earthy, bold and bright colors
  • Medium brown boots are an excellent choice
  • Brown boots work for formal occasions as long as the boot is dressy

Photo Credit: Pinterest, @krueger_patrick

Photo Credit: Pinterest, The Fine Young Gentleman

Photo Credit: Pinterest, Rowanrow

Photo Credit: Pinterest, He Spoke Style


Suede brown boots can be a little tricker to pair, but the key is to stick to neutral and earthy shades in the rest of your outfit.

  • When wearing light brown suede boots, it’s pleasing to the eye if there is another piece in your outfit that is light as well (i.e. shirt, pants etc).
  • Medium to dark brown suede boots go really well with earthy or deep colors
  • If you like bright pants for Spring, light to medium suede boots work great

Example of light boot with light shirt

Medium brown boots work well with earthy colors

Photo Credit: Royal Fashionist, @chrissleman

Photo Credit: Pinterest, Styleoholic

Photo Credit: Pinterest, Pinterest


Just like brown, black boots go with almost every outfit under the sun. If you’re not sure where to start, black is a great option.

  • Black boots are great for more formal outfits like suits
  • Black boots with broguing or a wooden heel is a great option to add flare
  • Brown boots work better with lighter colored bottom (i.e. light blue), black might be too harsh with a soft color
  • Black boots are great for guys who like a bit of a “motorcycle” edge in their looks
  • Black suede boots are a great option if shiny black seems too formal for you

Photo Credit: Idle Man, Idle Man

Photo Credit: Pinterest, @magicfox

Photo Credit: @magicfox, Pinterest

Photo Credit: Pinterest, Pinterest


After you have your black or brown pair of boots, grey is a great color to add into your rotation. In terms of pant colors, grey boots work with other neutral colors like blue, white and black, and pair really well with earthy colors like burgundy and green.

  • The easiest way to wear grey boots is by having a 2 neutral colors and one pop color (i.e. white t-shirt, blue jeans and green jacket). Don’t go past 3 different colors in your clothes
  • You can also wear all one color (i.e. all black or all blue) and have the grey boot be the pop of color
  • Don’t wear the same shade of grey in your pants and shoes
  • You can wear opposite shades like dark grey pants and light grey boots
  • You can wear a grey top (i.e. sweater or coat) and grey boots of the same color and it will look fine since the two items are away from each other

Photo Credit: Pinterest, @magicfox

Photo Credit: On Point Fresh, Style Mann

Photo Credit: Hello His, Pinterest

Other Colors

After you’ve covered your basic colors, you can have a little fun and experiment with secondary colors that can take your look to the next level.


Although they are more rare, green boots are a unique color to add into your rotation. The key is to let the green boot be the statement piece in your outfit and you can do this by wearing dark or neutral colors with the boots.

  • Blue, black, beige and white bottoms pair the best with green boots
  • When wearing green boots, it’s best to pair them with earthy or neutral colors
  • Green suede boots are an excellent fashion forward choice

Photo Credit: Pinterest, Alden

Photo Credit: Pinterest, Pinterest


If you really want to stand out of the crowd, white boots can be a fashion forward statement. Only word of warning: good luck keeping them clean!

  • The best way to wear white boots is with neutral colors like blue, black, white and grey
  • Cream boots can be a good alternative if white seems too bold

Photo Credit: Pause Magazine, Timberland


Burgundy boots can go two ways: classic or fashion forward. A leather burgundy boot is the classic choice because it can be worn exactly as a medium brown boot would. However, a brighter burgundy boot is great for making a fashion statement.

  • Burgundy goes really well with other earthy colors
  • Can treat a burgundy dress boot like a brown dress boot
  • Perfect way to add a splash of color to your boots without going overboard

Photo Credit: Pinterest, J. Crew

Photo Credit: Fabripagllari, J. Crew

Photo Credit: Pinterest, Thousand Yard Style


If red isn’t your thing, maybe blue is! Blue boots can be a fun color to add to your collection. Navy boots can be as subtle as black, but lighter blue boots can be your statement piece.

  • The best way to wear blue boots is with blue, black, beige or green bottoms and a neutral top
  • If you like blue, but don’t want the whole boot to be blue, go for a blue accent in the heel
  • A darker blue will be easier to pair than a lighter blue

Photo Credit: Pinterest, Pinterest

Photo Credit: Pinterest, Pinterest

Photo Credit: Look Book


Taking care of your boots will help them last longer, especially if you are going for full grain leather or suede. I know sprays and lotions seem like a marketing ploy to up-sell you, but some of them really work.

Overall Protection

The first thing to do is spray your boots with a Leather and Suede Protector.A protector will prevent scuffs, stains from setting in, and any water damage. You only need to spray your boots once a month. A universal protector will do the trick.

If you are “investing” in your boots and going for real Leather or Suede, follow the rest of the instructions below:

Leather Care

  • Just like our skin, leather needs moisture, so apply a good leather conditioning cream to the boot from time to time.
  • A damp wet cloth can help clean leather.
  • If your leather gets wet, let it dry naturally.
  • Get your boots shined from time to time.

Suede Care

  • You can brush your suede before and after applying the protector spray.
  • Small scuffs to your suede can be erased with a rubber eraser or a toothbrush.
  • If the stain is liquid, try using cornmeal or talcum powder on the spot. If it’s dry, try white vinegar (vinegar works great for salt stains as well).
  • Get a good suede brush to rejuvenate the fabric! Holding it above steam and then brushing can help the driest of suede come back to life.

Note: Keep in mind, water and suede don’t mix, so avoid wearing them in the rain or putting water directly on them when cleaning.

Shopping Notes


Your boots are made for walking, make sure you can walk hours on end in them. An excellent insole will help with this. Add your own insole if you like the boot overall, but wish the insole was a bit more cushioned.

Boots You Can Resole

If you are “investing” in your boots, make sure boots are resoleable. If 5 years down the line the only thing that’s messed up is the sole, you can make them anew!

Know What You Are Getting

You don’t need to buy the most expensive boots, but just make sure you’re not being ripped off.

Take Care of Them

Take care of your boots. Get good cleaners and protectors and apply them every one or two a months depending on how much you wear them.

Avoid Flashy Brands and Go for Quality Brands

Go for a brand that has a good reputation. There are new and old brands that make excellent shoes. Beware of flashy brands that will charge you for the label rather than quality.

Real Leather Stretches

Real leather stretches slightly as your wear it, so don’t buy your shoes too big. If you are getting a brand new pair of boots, chances are 0 to a few people have tried them on before, so expect them to be a bit snug at first. If you already bought boots and they stetched out on you, add in an insole to make them tighter.

Look at Customer Reviews for Sizing and Fit

If you’re shopping online, pay attention to customer reviews and how sizing worked for them (i.e. runs large or runs small) and order accordingly. Sometimes the description says true to size, which is not always the case. The example below shows the store’s fit note and the customer’s fit note, which are the opposite.

Says “True to Size”
Customer Reviews Say They Fit Big


What’s better round or square toe?

When it comes to dress boots, a slight round toe is the better and more modern option. Square toe can be hard to pull off because it looks too trendy and odd with jeans. Moccasin boots are the only exception because that’s how they are meant to be.

Photo Credit: Amazon, Johnston & Murphy

Can men pull off rain boots?

There are 2 ways to approach rain friendly boots: you can go for low cut rubber boots or find a pair of leather boots that are waterproof. I recommend going for the latter because you can wear them day to day and on rainy days. Rubber boots, on the other hand, can get hot and heavy, making you want to switch out of them once you get indoors. While shopping online, use the keyword “waterproof” and the style of boot you like (i.e. waterproof chukka) and you will find some nice options. Spray your waterproof boots with a protector to make them last longer.

Waterproof Chukkas

Rubber Boots

Photo Credit: Zappos, Zappos

Waterproof Apron Toe Boots

Photo Credit: Timberland

Can’t I just spray my regular boots with waterproof spray to make them waterproof?

Waterproofing sprays are made more for protecting the skin of your boot, rather than sealing the seams to prevent water from seeping in. If you are caught in light rain, it could work. However, if you get caught in a downpour and have a mile to walk, you’ll probably have wet feet by the end.

What should I look for in a boot?

  • Start with comfort. Boots should be comfortable, so you can wear them for hours. The footbed should fit your foot well. You can always put in your own insole if you’re getting a great deal on an excellent pair of boots, but the bed is a little off.
  • Next, quality. Fabric and stitch down construction are the other key factors that will determine whether you have a good boot or not. You don’t need to spend hundreds on a full grain leather boot if you don’t want to, but make sure you’re not paying a high price for bad leather.
  • Spending $200 to $300 on a good boot that will last you for years is worth the investment versus spending $80 on boots and having to replace them often. Also, who wants uncomfortable cheap boot that you have no desire to put on. Now that’s really wasting money.
  • If shopping online, find a place that has free shipping and free returns, so you can order 2-5 of your favorite pairs and have a try on session at home.

Can I wear boots with shorts?

Generally, I would say avoid wearing boots and shorts. However, there is one exception and that is a desert boot or suede chukka boot because they don’t go up the ankle as much. It’s best to wear low cut socks to keep up with the “summery” look.

Desert and Chukka boots with shorts

Photo Credit: Pinterest, Pinterest

If you don’t want to look like a mailman and also get a very bad tan line, avoid the following:

Avoid any high boots or socks with shorts

Photo Credit: Pinterest

You made it to the end of the guide. You’re a boot expert now! If you have any questions, don’t hesitate to reach out. Happy Boot Shopping!

Supreet Chahal

Supreet is a Fashion Stylist from San Francisco, CA. She helps both men and women establish a sense of style and dress with confidence. If you want to work 1:1 with Supreet, visit If you're a guy looking to learn more about style, check out, a site dedicated to teaching men how to dress well.

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