Why Your Dress Shirts Are Making You Look Amateur AF And How To Fix It

There’s nothing funnier than a guy in an ill-fitting shirt who thinks he looks aces. He’s got the right pants, shoes are polished and tight, jacket on point but his shirt has enough room around the waist to hide six basketballs or the second button from the top IS PUTTING IN WORK trying to keep the shirt closed.

“The biggest issues guys are facing with dress shirts today are pretty standard,” Sam Smith explained, “their shirt doesn’t fit because it’s either too long, too big or just too billowy.”

Smith is one of the guys behind Hugh & Crye — an online retailer of better fitting menswear. Based in Washington, DC, the company started with a simple concept — fit comes first. They believe fit is about feeling good when you button up your shirt in the morning. It isn’t just about being correct, it’s about being yourself. If something doesn’t quite fit – your body, your values, your character – it throws everything off balance. They even havean online custom fit finder  so you never buy a poorly-fitting dress shirt again.

If you’re forced to buy off the rack, you’re going to fall victim to at least one, or all, of these issues that happen with the typical plastic-covered or million-pinned floor models. Smith has four reasons why your shirt is making you look bad and what to do to fix the stitching glitch.

The Shirt Is Too Damn Long

The shirt hem should be long enough for you to comfortably wear the shirt tucked or untucked. Two ways to look for this: First, when your shirt is untucked and buttoned, the tail should fall just past the back pockets of your pants. Note, we say “pants,” and not jeans, as most guys wear their jeans a little low on the waist. The second way to know whether you have the right length is to tuck in the shirt. When tucked in, raise your arms above your head and see if the tails pop out from your pants. If so, your shirt could be a little too short.
There’s Too Much Damn Fabric

The best dress shirts fit comfortably around the chest, under the armpits, and across the upper back, giving you a full range of motion. A fitted shirt will feel snug, but not too tight. Your chest should “fill out” the shirt in a way where your body is discernible under the fabric. Note: If the buttons pull when you’re standing still with your arms down, it’s too tight. The same thing is true in the waist- the shirt should be tapered from shoulders to waist to accommodate the shape of your body. Most mass-market dress shirts leave way too much fabric in the waist and body, contributing to the dreaded male muffin top.

The Sleeves Are Too Damn Long

Most guys know that you want to show a little bit of sleeve under your jacket – but not too much. Too little, and it looks like you’re swimming in your jacket – but too much, and a well-fitting jacket can look far too tight. We think the cuff of your shirt should fit right at the base of the thumb. From there, feel free to roll up your sleeves however you’d like – just keep it clean.

The Shoulders Are Way Off

To accommodate large swathes of the population, most brands cut their armholes loose and low leaving too much fabric in the shoulders. This can make a fit guy look chubby, and wrinkles quickly due to the abundance of fabric. The seam where the sleeve attaches to the body of the shirt should hit you on your shoulder – right at the top of it. It’s a flattering look for any guy, and will probably be more comfortable, too.

Chris Illuminati avatar
Chris Illuminati is a 5-time published author and recovering a**hole who writes about running, parenting, and professional wrestling.