Does your shirt actually fit you?

Do you ever put on a button down and just feel… off?

Like you bought a quality shirt from a good brand, but something still doesn’t look right when you check the mirror?

Here’s the thing: even a well-made shirt can look cheap if it doesn’t fit your body properly. And conversely, a more affordable option that fits correctly will always look better than an ill-fitting premium piece.

That’s because fit trumps everything else.

That’s why I want to walk you through the 4 fit mistakes that instantly ruin your button down style game.

Let’s dive in.

Who I’m Following

Whenever someone asks me who some cool celebrity style stars are, Ryan Reynolds comes up as a great example of smart casual style. His subtle pops of style through layering, eyewear and prints make his style perfect for the every-guy.

• Ryan Reynolds Instagram – Here’s an IG account that I follow that breaks down Ryan’s outfits.

Mistake #1: Buying shirts with shoulders that extend past your shoulder point

You’re automatically reaching for Medium or Large without checking where the shoulder seam actually falls on your body.

But here’s the thing – this is the most critical measurement for any shirt since it affects your entire silhouette. When you grab your usual size and the shoulder seam hangs past your actual shoulder bone, you create that droopy, oversized look that screams “I borrowed someone else’s clothes.”

Here’s how to check:

1. Stand naturally and look in the mirror.
2. The seam where your sleeve meets the shoulder should hit right at the corner of your shoulder bone.
   1. If it’s hanging off the edge, the shirt is too big.

And here’s what most guys don’t realize – a tailor can’t fix shoulder fit. This has to be right from the start.

Mistake #2: Choosing shirts that pull at the buttons when you move

You’re sizing down because you think “fitted” means “tight” – and creating that strained, uncomfortable look.

I see this constantly with guys who want to look sharp but end up looking like they’re about to hulk out of their clothes. When you pick a shirt that’s too small through the chest, those horizontal pulling lines across your chest destroy any chance of looking polished.

Quick Test 1:

1. Sit down in your shirt.
   • If the buttons show any tension or pulling, size up.
2. You should also be able to pinch about an inch of fabric on either side of your chest and torso without the shirt feeling loose.

Quick Test 2:

1. Reach your arms straight ahead like you’re about to do a squat.
   • If your shirt is uncomfortable and pulling at your back, your shirt is too tight.

Solution: Try different fits like “trim” vs “tailored” vs “slim” vs “regular” and see which one is made for you. In-between fits? You can always take in shirts, but you can’t really let them out. Avoiding buying shirts that are on the smaller side.

Remember: you want to look intentional, not like you’re struggling to breathe.

Mistake #3: Settling for sleeves that balloon around your arms

You’re accepting baggy, shapeless sleeves because you think that’s just how shirts fit – but you’re killing your entire silhouette.

Nothing looks sloppier than sleeves swimming in excess fabric. When your sleeves are too loose through the arms, your entire upper body disappears and you look like you’re wearing a tent.

However, there’s a sweet spot here: You should be able to grab about 1-2 inches of fabric under your bicep when you raise your arm to the side. Any more than that and you’ll look shapeless. Any less and you’ll feel restricted.

For cuff length, your sleeve should end right at the dimple of your wrist when you flex your hand toward your thumb.

Mistake #4: Wearing shirts that pass your zipper and hang below your back pockets

Your untucked shirt should fall between the middle and bottom of your zipper – never below your back pockets.

Too long and you look like you’re wearing a dress. Too short and your belt shows when you raise your arms, which looks juvenile. The perfect untucked length hits right at the middle of your zipper and covers the top of your back pockets.

Quick test:

1. Raise your hands up (you don’t need to exaggerate when reaching up, do a natural motion of grabbing something above your head)
   1. If your stomach shows, the shirt is too short.
   2. If the hem goes below your back pockets, it’s too long.

Most guys get this wrong because they assume all mediums or larges should fit the same. But brands cut lengths differently, so always check this measurement.

Tip: Check the length of your favorite fitting button down (where neck and shoulder meet to the bottom hem of the shirt). Some stores and brands will tell you the shirt length online and you can compare numbers to know if it will fit you.

What you learned

Here’s what we covered:

• Shoulder seams are non-negotiable and must hit at your shoulder point
• Chest pulling makes you look uncomfortable and poorly dressed
• Sleeve fit should follow your arm shape without excess fabric
• Length matters for creating clean, intentional proportions

The key is understanding that great-fitting button downs aren’t about the brand name or price – they’re about getting these four details right.

Your next action step

Try on your favorite button down right now and check these four points in the mirror.

If the shoulders fit correctly but other areas need work, book an appointment with a local tailor this week – most adjustments cost around 2-3 fancy coffees and make a dramatic difference.

Measure your favorite button down:

1. Shoulder seam to shoulder seam (to know your shoulder width)
2. Where the neck and shoulder meet to the bottom hem of the shirt (to know your length)

For new shirts, here are brands that consistently deliver quality and/or multiple fit options: Rails, Reiss, Bugatchi, Billy Reid, Ben Sherman, Taylor Stitch, Bonobos, and Hugo Boss.

Need to go custom without breaking the bank? Go with Proper Cloth or Charles Tyrwhitt

Remember – invest in quality pieces that fit well rather than settling for cheaper options that never look quite right.

PS – You know what I love about these button-down tips?

They prove that great style isn’t about having perfect taste – it’s about understanding the fundamentals that actually work.

The Style Game Plan gives you these same fundamentals for your entire wardrobe, plus my exact 10-step system that takes you from morning overwhelm to effortless confidence.

Ready to become the guy who just “gets it” when it comes to style?

Click here to get The Style Game Plan and start your complete transformation today.