All Oversized Everything: How To Go Big Without Going Home

There are typically two concerns when buying something oversized: Does this make me look like a child playing dress up? Or: Do I look like a crazy person? But, when done right, one oversized piece is all it takes to turn your outfit up to 11. Suddenly you'll get loads of compliments, without doing anything as drastic as that last haircut you got. So, what's the key to pulling off all things intentionally oversized? Understanding balance. Ahead, learn to let the oversized piece of your choice do the talking, without taking up all the conversation.
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The Oversized Sweater
Everyone needs an oversized turtleneck to curl up in and hide from the world come winter. This one's got the slouchy, extra-long sleeve trend covered, but it won't completely lose your shape. Pair it with black skinnies and boots, and you've got your fall-to-winter uniform.
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The Oversized Jeans
The key to buying oversized jeans isn't always sizing up — instead, find a pair with an intentionally-loose silhouette that fits around the waist, but is still baggy in the leg. Topshop is your place to score the perfect ones.
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The Oversized Outerwear
To embrace oversized outerwear, you have to get past the idea of wanting your coat to be figure-flattering — that's just not the point when it comes to these boxier buys. Keep your accessories on the more prim side. Here, a sleek black loafer lets you rock the more avant-garde silhouette while feeling more polished than cartoon-ish.
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The Oversized Shirt
With a baggy shirt, you have a few options. You can go big all over with some oversized-yet-structured jeans, or balance out the larger top with a more form-fitting bottom, like a skinny jean or legging.
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The Oversized Trouser
How to bring the oversized trend into the workplace? Try a trouser that's loose-fitting but slightly cropped. It's a cool, undone look when paired with a thin sweater and flat shoes — and maybe a blazer on top, too.
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The Oversized Sunnies
Pair these with an effortless, boyish look, a croc bag, and a coffee in hand and you might just be mistaken for Mary-Kate Olsen. Just make sure you try on oversized sunnies before you buy — you'll want to find a pair that's just the right amount oversized for your face.
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The Oversized Dress
Forget the rules that dresses are supposed to be oh-so ladylike and traditionally figure-flattering. An oversized sack dress in a bold-hued satin fabric can actually feel dressy. Opt for one with a sturdy structure that's more architectural than just a sack, and maybe add a heel — some extra height always works well with oversized pieces, especially if you're petite.
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The Oversized Moto Jacket
Cropped moto jackets feel so "been there, done that." Change up your go-to silhouette with a classic leather moto jacket that's more on the boxy side.
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The Oversized Cardigan
Meet your new Sunday go-to. With a boyfriend cardigan, don't overthink the rest of the outift — just a destroyed jean and your favorite white tee will do the trick. Coziness is the goal, here.
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The Oversized Boot
Not only will these come in handy when New York City turns into a snowy sludge maze, but they also make a street-style-worthy statement when paired with destroyed jeans and a graphic tee. They can give any casual outfit a more edgy, fashion-forward spin.
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The Oversized Scarf
It might look like you wrapped a blanket around your neck, but that's what you're going for. Nothing will keep you warmer when the temps drop than a super-cozy blanket scarf. Pick one in a fun yet versatile color palette that matches all of your usual cold-weather outerwear, and you'll never want to take it off.
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The Oversized Blazer
Opting for a blazer that's boxy and a bit oversized instantly makes it feel less like a stuffy, corporate staple and more like a cool-girl must-have. It's perfect for in-between autumn weather, and pairs easily with a button-up shirt and jeans.
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The Oversized Denim Jacket
A longline denim jacket is a great way to avoid wearing one that makes you look like you stepped out of a '90s sitcom. It goes with pretty much everything, but is especially elongating when paired with a long, flowy pant. And, of course, you've just got to go for the frayed hem.
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The Oversized Hat
Swap your high-school beanie for something more dramatic and sophisticated, because why not? Just make sure your wide-brimmed hat fits snugly on your head, or a gust of wind is sure to knock it right off.
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The Oversized Jumpsuit
If you're an overalls pro by now, you're ready to move on to the next level: the baggy jumpsuit. With the new shape, the less form-fitting, the better — but a cropped culotte shape keeps it from feeling like you're drowning in fabric. Throw on a tight long-sleeve tee underneath and your usual black bootie, and you're out the door.
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