Why I Stopped Overlooking Oversized T-Shirts

One of the lasting life lessons I learned from my first “real” relationship was the power of an oversized T-shirt.

My ex had a well-curated collection, mostly from Uniqlo or Frank And Oak. Each one was simple, streamlined and free of logos, patterns or contrast stitching. I — a girl with a taste for garish colour blocking and an aversion to wardrobe basics — was mystified by this assortment. Why have so many versions of seemingly the same thing?

In finding my fashion taste, I had long overlooked the baggy tee. It was a boring blanched vegetable in a world of sweet sartorial desserts. Historically, I’d much rather wear a button-down with a necktie, a dress with puffed sleeves or a kitschy sweater vest. And yet, the more time I spent around this selection of plain pieces, the more I came to appreciate it.

Each time I would “forget” to bring comfy clothes to change into when I went over, I would be generously tossed a tee to take home with me and own for weeks at a time. I loved the way I felt wearing it. The drop-shoulder stitching gave it a relaxed structure, while the oversized effect gave me an androgynous edge. To my pleasant surprise, its blatant basicness was not stale; it was a blank slate ripe for accessorizing. I paired it with tonal Bermuda shorts and leaned into carefree boyishness. I layered it atop a maxi skirt and piled on chunky silver necklaces. In its unadorned appearance lived a world of possibilities — from The-Row-level monochrome pairings to louder, well-layered looks. How had I not realized?

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Photography via Launchmetrics.com/spotlight

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Look to any crop of recent runways and you’ll find a sea slouchy shirt inspiration. Across the Spring 2025 collections, Gabriela Hearst offered a hardened leather variation, while Ann Demeulemester played with textures by layering a distressed tee over a lacy frock (above). Christian Wijnants and Ermanno Scervino leaned into the stripped-back sexiness of a shapeless chemise with equally lax pants and minimal accessorizing (below).

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Photography via Launchmetrics.com/spotlight

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In my discovered appreciation of the oversized top, I’ve found myself shopping in the men’s section, side-stepping the pink tax and finding the T-shirt options to be even more plentiful. I’ve learned to appreciate the simple yet detailed nuances of fabric; how a boxy, starchy design will hang differently than a flowy lightweight pick. And once in a while, as a little styling challenge, I’ve found myself pushing past my penchant for feminine silhouettes and walking into the world wearing a beanie, way-too-big cargos and my baggiest oversized T-shirt.

I now know it’s the basis of any well-seasoned wardrobe, so below, I’ve outlined the best picks on the market. That romantic relationship may have not worked out, but our shared appreciation of the no-frills chemise will remain. And that’s it’s own kind of bond.

The best oversized T-shirt picks to shop now

Uniqlo crew neck T-shirt

Available in 13 shades and made of quality heavy-weight jersey, the Uniqlo crew neck is a classic for a reason. I will always be loyal to this design as my first introduction into the oversized tee world. It’s chic, cozy, and under $20.

Kotn Luxor Jersey tee

The Luxor Jersey tee is a breathable, lightweight T-shirt made from organic cotton. Designed with a textured finish, mid length sleeves, and a relaxed fit, it embodies what Kotn does best: balancing casual staples and elevated design elements.

Frank and Oak The Loose T-shirt in taupe

This baggy tee has a sleek put-together effect, thanks to its exaggerated long length, wide shape and modern greige hue. Made of organic cotton, it’s crafted to last forever — like any good oversized T-shirt is.

Hanes men’s Beefy t-shirt

Nothing guarantees comfort like a humble Hane’s T-shirt. Sold in a pack of two and available in an array of shades, this 100 percent cotton crew neck is ideally oversized for all your layering needs.

Everlane box-cut tee

If you tend to prefer cropped lengths, Everlane’s tee is right for you. It hits just below the waistline so it can be easily tucked or left to effortlessly billow. Plus, it comes with the option for a pocket.

Gap organic cotton T-shirt

Bring butter yellow into winter with this pastel tee. With long short sleeves that hang in a boxy shape and a below-the-hip length that lays loosely against the body, it’s has a vintage appeal that would pair perfectly with 501s.

COS lightweight brushed-cotton T-shirt

A COS classic, this men’s cotton-jersey has effortless drop-shoulder detailing and a fit that leaves room for easy movement. To style, pair with slouchy navy trousers and a coordinating cardigan for a two-toned effect.

Another Tomorrow luxe seamed short sleeve

If you’re looking to treat yourself to a luxury T-shirt, Another Tomorrow is the place to go. This pick stands out for its sharp details — like the dramatic drop-shoulder, curved hem and statement back stitching.