The Fit Guide for Men Who Are Tired of Looking Like They Borrowed Clothes
At some point, every guy has looked in the mirror and thought, ‘Is this shirt supposed to fit like that?’
Photo Credit:@wyntonaustin
I’ve been there—standing in a fitting room, staring at myself in jeans so tight I felt like I owed the denim an apology. Or worse, I’ve bought a blazer that looked great on the hanger, only to realize I couldn’t lift my arms past my waist. Clothes are supposed to fit you, not fight you.
The truth is, bad fits happen. More often than not, they’re the silent killers of a good outfit. The sleeves that flap like wind socks, jeans that could double as parachutes, or shirts that look like they’re swallowing you whole—if you know, you know.
Here’s the good news: finding the perfect fit isn’t rocket science. You don’t need a tailor on speed dial or a ruler in your pocket. With a few simple rules—like paying attention to inseam lengths and ditching shirts that could double as tents—you’ll start spotting what works and what doesn’t. Clothes that fit right don’t just look good. They make life easier.
This guide? It’s the shortcut to never looking in the mirror and thinking, ‘Well, this is awkward’ again.
The Fit Breakdown: Key Clothing Items
Now that you know the basics, let’s talk about the clothes you actually wear. Here’s how they should fit so you can stop second-guessing yourself.
1. T-Shirts
Not Here Tee
Jungles
$70
Orlando Tee
ALLSAINTS
$95
The perfect tee skims your body. Not clingy, not baggy—just a solid middle ground. The length? Mid-hip. Anything shorter, and you’re accidentally wearing a crop top. Anything longer, and people will start asking where you bought your nightgown.
2. Jeans
Wrangler
Men's Bootcut Jean
$69.99
Jeans should feel like jeans, not spandex or a parachute. Slim-fit jeans work for most guys—no weird bagginess, no circulation issues. If bending over sounds like a rip waiting to happen, size up. If you can fit both hands into the waistband, size down. Finding jeans shouldn’t feel like hard work.
3. Dress Shirts
Mendez Knitted Shirt
PAIGE
$229
A good button up- shirt should sit on your shoulders like it was made for you, not some other guy. As for the collar? You should be able to slip two fingers in comfortably—if you’re gasping for air, it’s time to size up.
4. Blazers and Suit Jackets
Casual Everyday Blazer
WAO
$248
The shoulder seams should end exactly where your shoulders do—no “my big brother lent this to me” vibes. And if you can’t button it without feeling like you’re holding your breath for dear life? It’s not your jacket. Let it go.
5. Pants and Chinos
River Relaxed Chino Pants
NEUW
$199
Stick to straight or slim cuts. If you’re constantly pulling them up or if they balloon out like you’re preparing for takeoff, they’re not the ones. The right pair of pants stays put, looks clean, and gets the job done—just like you.
The Basics of a Perfect Fit
Once you know what to look for, spotting a bad fit becomes easy—like spotting someone trying way too hard at a party. Here’s the deal:
Shoulders
If your shirt’s shoulders hang halfway to your elbow, you’re one step away from looking like you stole your dad’s dress shirt. On the flip side, if the seams are cutting into you, congrats—you’re now the proud owner of a denim straightjacket.
Sleeves
Your sleeves should end right at your wrist bone. Anything longer, and you’ll look like you’re gearing up for your deep-sea audition in Finding Nemo.
Pants Length (Inseam)
Pants that puddle at your ankles say, “I gave up.” A clean break at the shoe says, “I get it.” Small difference, big impact.
Shirt Length
Your t-shirt shouldn’t swallow you whole. If it’s covering half your back pockets, it’s too long. Unless you’re still channeling your 2005 emo phase, let’s aim for something that actually hits mid-hip.
