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You've come to the right place to learn how to style an oversized shirt. As a fashion editor and practicing androgynous girlie, I just so happen to be the industry’s (self-declared) leading expert on the subject. In fact, I wore two just today.
Whether you’re turning a large rugby shirt into a dress or putting on a billowy button-down, oversized shirt outfits are a Fashion Person’s secret weapon. The drastically outsized silhouette feels theatrical and attention-grabbing in the best possible way, while still giving off an effortless feel. It gives the wearer more fabric to play with and the observer more visual surface area to enjoy. Or, as we say in the business: The looser the fit, the chicer the feel.
Glamour’s oversized shirt wish list
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Beyond aesthetics, wearing a loose-fitting top—or any voluminous garment, for that matter—makes a powerful statement that should not be overlooked. It allows you to take up space in the world, to be unapologetic in your existence. You don’t have to make yourself smaller, and you don’t have to embrace the hyper-revealing in order to look sexy. You can exist separately from all of these things. In this way, wearing an oversized T-shirt or button-down isn’t just wearing an oversized shirt. It’s a way of presenting yourself to the world—and yes, okay, it looks really chic too.
Here are some ways to make the look feel authentic to your personal style.
1.Belted at the waist
While I love a “so big you could drown in it” fit, embracing a little tailoring almost always guarantees a stylish look. Throw on a narrow belt to make your favorite boyfriend shirt and wide-leg pants feel more appropriate for your proportions, while still very much retaining that relaxed fit. The cinching effect will actually emphasize your look’s exaggerated silhouettes even further.
2. As a crop top
Similar to a leather belt, tucking your biggest oversized tee, jersey, or rugby shirt into your bra will create a quick tailored look. Your comfy-casual outfit will still feel artfully baggy, just slightly less so.
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3. With a little side tuck
As you’ll soon learn, most tricks for pulling off a baggy shirt involve some form of tucking—whether that’s a full tuck, a half tuck, or a side. All are great choices I use regularly, but the latter is easily the most underrated way to wear oversized shirts. It’s laid-back, cool, and looks great under a crisp suit jacket.
4. Layered over a long-sleeve tee
This trick for how to style oversized shirts is one early-1990s relic I’ve welcomed back with open arms. Layering an oversized T-shirt atop a long-sleeve tee gives off that cool, ’90s vibe all of us seem to be striving for these days. My advice? Mix stripes and an oversized graphic tee to channel an edgy, punk feel.
5. With a chill button-down
If you’d like actual footage of me getting dressed this morning, this street style shot is as close as it gets. I pretty much copy-and-pasted this outfit inspiration for running errands: slouchy pants, a baggy T-shirt, and a striped button-down in a bright hue—which I, likewise, matched to my sneakers. Another win for the overlarge shirt community.
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6. With equally oversized bottoms
It’s a common misconception that a dramatically large shirt must be paired with a fitted trouser, skinny jeans, or a slim-fit skirt for balance. And while that theory certainly holds true in certain situations, it’s not at all fool-proof. I say embrace the volume throughout by styling with a pair of longline shorts or a bubble-style midiskirt. You can bring the “balance” aspect into play with a pair of sleek boots.
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7. As a shirtdress
With years of experience shopping in the men’s department, I’ve turned almost everything you can imagine into a dress. Jackets, button-downs, blazers, T-shirts, cardigans, rugby shirts—you name it. So take inspo from this street style look, and turn your dad’s vintage polo into an unexpected and chic dress.
8. With cargos
There’s just something so delightfully contradictory about styling polished workwear with utilitarian streetwear staples, like sneakers or cargo pants (or any other such fashion trend). Channel that combo yourself with your favorite oversized button-down. Believe me, it’ll soon be at the top of your rotation.
9. Buttoned all the way up
If it’s the weekend, by all means, let your collar hang wide open. But if you’re in any setting that requires you to look put-together, button that baby all the way up. It makes your look feel intentional and high-fashion. Finish with a slicked-back hairstyle and accessorize with a pair of metallic statement earrings, then thank me later.
10. Wrapped around your waist
Remember when you couldn’t leave the house without a flannel knotted around your waist? I say we bring back that same concept—but with oversized button-down shirts. Layered over another dress shirt, the look actually feels really chic.
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11. Half-buttoned with jeans
I first saw this styling hack years ago on a Fashion Week model who had just walked a prestigious runway. Since then I’ve made it my mission to work it into my big-shirt repertoire. The look is super simple to pull off—just layer a button-up over a white tee and tuck in both to a pair of baggy jeans. Add a belt and fasten a few buttons, swipe on a red lip, and you’re good.
12. Doubled up
If none of these outfit ideas feels unique enough for your style (and if so, props to you), might I suggest this out-of-the-box styling tip? Pop on dual oversized tops for a layering moment of epic proportions. Just make sure the pants you tuck them into are also pretty baggy, so you don’t end up with diaper bottom.
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