30 Times Going Bigger Meant Looking Better

Not too long ago, skinny jeans, miniskirts, and body-con dresses could be found in almost any girl’s night-out repertoire. And, truthfully, many of these still are. But, the fashion industry has gotten the memo: Vessel-constricting apparel does not a lady make. As far as we're concerned, baggy's not back — it's here for the long run.
So, consider the slides ahead your outfit inspiration wish list of non-Spanx-required looks that will allow you to have your holiday feast and eat it, too – yes, even that extra helping of your mom’s famous mashed potatoes. And, luckily for us, oversized fashion is far from frumpy and shapeless, which makes winter dressing a whole lot more exciting. The loose-fit trend is ideal for layering, appropriate from day to night, and will keep you extra-toasty in the constant battle against Mother Nature.
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So, if you’re looking for comfortable silhouettes that will be flattering throughout Thanksgiving dinner, the next day, or all season long, we’ve gathered the very best. You and your food baby can thank us later.
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Photo: Courtesy of Net-A-Porter.
Introducing the LGSD: the little grey sweater dress, a.k.a. your new winter staple.
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Photo: Courtesy of Zara.
Make loungewear daywear by combining a boxy turtleneck with slim-fit sweatpants.
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Photo: Courtesy of Rachel Comey.
Tuck in the front of an oversized dress for a pseudo-high-low effect.
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Photo: Courtesy of 6397.
Boyfriend jeans? Check. Boyfriend jacket? Check.
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Photo: Courtesy of Agnona.
Oversized coat + cutouts = wearable art.
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Photo: Courtesy of Bally.
A belt may seem restrictive, but it's also adjustable. You know, depending on what course you're currently on.
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Photo: Courtesy of Farfetch.
A tunic-length top is the easiest of oversized essentials. Standout prints are optional but recommended.
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Photo: Courtesy of Brunello Cucinelli.
For a flirty look, pair a tunic with a statement skirt.
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Photo: Courtesy of Cynthia Rowley.
Goodbye, body-con. Hello, flouncy frock.
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Photo: Courtesy of Apiece Apart.
Oversized garments look effortless when color-blocked in seasonal hues.
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Photo: Courtesy of McQ Alexander McQueen.
Your grandpa's sweater vest has never looked better.
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Photo: Courtesy of Derek Lam.
Who says a voluminous skirt needs to be paired with something tighter on top?
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Photo: Courtesy of J.Crew.
Because wearing slightly loose-fitting clothing takes us one step closer to Jenna Lyons' aesthetic.
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Photo: Courtesy of Topshop.
Embrace your inner Edie Sedgwick with the biggest and shaggiest coat you can find.
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Photo: Courtesy of Adam Lippes.
Oversized separates in similar hues and widths form the cleanest of lines.
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Photo: Courtesy of A.W.A.K.E.
The ultra flare shape and graphic print make these bell-bottoms less disco and more Friendsgiving-dinner ready.
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Photo: Courtesy of J.Crew.
Our kind of winter tux.
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Photo: Courtesy of Free People.
Doesn't get easier than a printed jumpsuit that can be layered over long johns or under chunky sweaters for the duration of the season.
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Photo: Courtesy of Forever21.
Cocoon coats instantly create a mod moment.
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Photo: Courtesy of Jasmin Shokrian.
Because oversized style means sometimes sporting a handbag that lets you store your hat, gloves, and chunky scarf.
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Photo: Courtesy of Maison Kitsuné.
We couldn't say it better ourselves.
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Photo: Courtesy of J.Crew.
Combine business with pleasure by wearing a knee-length embellished skirt under a white, tailored top.
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Photo: Courtesy of Nasty Gal.
Sequined sweater that doubles as a tunic: yes. Denim jacket over sequined sweater that doubles as a tunic: double yes.
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Photo: Courtesy of No. 6.
And, just like that, matching, boxy separates become a dress.
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Photo: Courtesy of Alice + Olivia.
A high-rise fit draws the eye to the narrowest part of your waist, but the parachute shape gives your pants plenty of room to move on the dance floor.
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Photo: Courtesy of Arthur Arbesser.
Like your old school uniform...but baggier, boxier, and so much sleeker.
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Photo: Courtesy of Urban Outfitters.
If only Coachella were in the winter...
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Photo: Courtesy of Shopbop.
Black (and oversized) everything.
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Photo: Courtesy of Nasty Gal.
Just because it's oversized doesn't mean you have to sacrifice your shape. This flared skirt highlights curves while the top remains relaxed and comfy.
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Photo: Courtesy of Maiyet.
Or, use a belt to cinch the smallest part of your waist while leaving the rest of your layers loose.
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