Okay so I’ve always thought frat guys had this effortless cool style thing going on, right? Like they just roll outta bed looking put together. Total mystery to me. So last semester I decided, screw it, I’m gonna figure out how they actually dress and try copying it myself. Figured I’d document this mess step by step.
Starting Super Wrong
First big mistake: Thought it was all loud Hawaiian shirts and backwards baseball caps from old frat party pics I saw. Grabbed this awful bright orange shirt covered in pineapples my uncle left behind, some old gym shorts, and slapped on a faded Bruins cap backwards. Walked around campus feeling ridiculous. Got exactly zero “cool” vibes. Just a dude who looked like he got lost after a beach bonfire. Hated it. Hated myself. Needed a hard reset.
Actually Paying Attention
Next day, camped out near the main frat houses with my crappy coffee pretending to read a book. Just straight-up stared at dudes walking in and out. Took actual notes on my phone like a weirdo. Here’s the patterns I saw:
- Short-sleeve button-downs, mostly: Not the touristy ones. Think solid colors like baby blue or heather gray, some chill stripes.
- Polo shirts were everywhere: Mostly relaxed fit, collars popped or unpopped, seemed like decent brands but worn out.
- These weird shorts: Called chinos? Not super long basketball shorts, not tight either. Like 7-inch or 9-inch inseam maybe? Saw khaki, olive green a lot.
- Shoes: Seriously dirty leather boat shoes or beat-up white leather sneakers. Sometimes flip-flops if it was hot.
- Base layers: Plain white or black t-shirts underneath everything.
- Winter stuff: Big Patagonia fleeces or down vests. Like, seriously huge.
My First Attempt After Stalking
Hit up a thrift store downtown. Mission: Find the items from my spy list.
- Found a faded navy blue Ralph Lauren polo shirt ($4.99). Collar was a little floppy.
- Scored some light khaki-colored chino shorts ($6.50). Little baggy.
- Almost missed a pair of crusty brown Sperry boat shoes ($8.00). Smelled faintly of feet and old leather. Perfect.
- Grabbed a generic white tee from the pile ($1.99).
Tried it all on at home. Polo felt stiff. Shorts needed a belt or they were sliding down. The shoes? Sized wrong. Squeezed my pinky toe. Added an old baseball cap forwards this time. Looked in the mirror. Less “lost tourist,” more like… the guy helping you at a golf course starter hut? Meh.
The Fit Fix
Decided the clothes just hanging off me was part of the problem. Everything was too big or too stiff. Threw the polo in the washing machine twice with fabric softener to beat it up. Tried cuffing the shorts twice so they hit just above the knee. WAY better. Found a thick brown leather belt from my dad. Squeezed my feet into the boat shoes hoping they’d stretch. Took the hat off entirely. Swapped the white tee underneath for one that was thinner, less stiff cotton.
The Final Test (And Realization)
Wore it all to a big outdoor BBQ thing happening near Greek row. Kept it simple: Navy polo (weathered now), cuffed khaki shorts, that beaten leather belt, the boat shoes I’d semi-broken-in, thin white tee peeking out slightly. No hat.
Stood around holding a soda. Felt awkward but… different. A couple guys just nodded at me like, yeah, you’re fine. No weird looks. No one laughed. Then it kinda clicked watching them: It’s not really about specific brands, it’s about clothes being comfortable, worn-in, and fitting mostly relaxed. It’s low-key. Messy hair? Fine. Shoes scuffed? Good. Shirt a little rumpled? Whatever.
Got home, threw the polo on the floor. That’s the look now. It’s about pretending you didn’t try. Guess the “cool” is just confidence mixed with clothes that let you move without thinking much. Kinda basic once you strip away the brand hype. Not gonna lie, it works.
