The Obtainer - 5/19/25, Monday

Valet.
The Obtainer

Monday,
May 19th Edition

Cory Ohlendorf

A T-shirt is a fundamental piece of your wardrobe. They’re timeless, but there are always updates and trends to play with. Case in point: The bigger, boxier, beefier tee you need now.

- Cory Ohlendorf, Editor in Chief ⋯ @coryohlendorf

 

Boxy T-Shirts Are Big (Literally)

You’ve probably noticed that the silhouettes of menswear continue to balloon in proportions. Everything from jeans and button-downs are bigger these days. A touch baggy, with a flowy and roomy vibe. And this extends to even the most basic of wardrobe staples. Yes, oversized T-shirts are suddenly everywhere. And as summer 2025 heats up, the boxy tee has emerged as the season's MVP. Loose in the shoulders, generous in the sleeves, and cut with a cropped, square silhouette, these tees aren't just about comfort—they're about attitude.

They nod to '90s skate culture, early-2000s streetwear, and even vintage military basics, but feel totally modern when styled right. Toss one on over a tank, wear it with pleated shorts or poolside with trunks—it works wherever you're going. And unlike slim-fit tees that can cling in the heat, these breathe easy. This summer, the coolest move might just be going bigger.

Our Picks

Oversized T-shirt,
$54 / $36 by Skims

 

Heavyweight box crew T-shirt,
$58 by CDLP

Heavyweight relaxed T-shirt,
$65 by Reigning Champ

 

AIRism oversized T-shirt,
$14.90 by UNIQLO

 

Mock-neck oversized T-shirt,
$35 by Los Angeles Apparel

5 Stylish Items to Buy This Week

This clever reusable film camera ($99) blends retro charm with modern convenience. Designed for beginners, it features a focus-free 31mm f/9 lens, built-in flash (powered by a AAA battery), and manual film advance and rewind. Compatible with any 35mm film, it's an eco-friendly alternative to disposables, reducing landfill waste. Lightweight and available in vibrant colors, the Reloader is ideal for capturing candid moments at events or during travel—especially if you want real photographs shot on film. With a simple focus-free lens, it's a foolproof option that's a whole lot of fun.

See all 5 products »

 
Smart Buys

The sales and discounts our team is currently watching.

 

Todd Snyder’s knit sportcoats are the epitome of soft tailoring, so there’s none of the padding that makes a blazer stuffy. They’re made in Italy from 100% cotton, so they’re light and breathable.

$698 / $344
by Todd Snyder

 

Nike’s rugged C1TY sneakers are ready for anything. The mesh upper keeps the fit breathable, while the reinforced sides and toe box help protect your feet from the elements.

$100 / $74.97
by Nike

 

Want an on-trend Western-tipped belt without going full “cowboy” with the aesthetic? This understated option is a more restrained look, but still has that signature metal tip.

$79.50 / $55.65 by
Johnston & Murphy

 

Want more?
See all 27 sales »

 
Worth a Read

The best stories from around the web.

 

To render yours cooler, breezier and more modern, let it flop open like a devil-may-care cardigan.”

 

Double-Breasted Blazers Feel Cool and Modern—If You Wear Them Like This

 

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The Wall Street Journal
 

According to the model and menswear expert Richard Biedul, buying menswear in summer is a minefield.”

 

The Only Summer-in-the-City Style Guide You Need

 

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MR PORTER
 

I take it out of my hand luggage because it always sets off the detectors; that way, they don't have to pass everything. They just take the candle, they swab it, and then I'm good to go.”

 

Antoni Porowski Won’t Travel Anywhere Without This $99 Candle

 

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Thrillist