
Update: This post was originally published on Dec 7, 2014.
Oversized clothes get a bad rap as the items you reach for when you don't want to try. For days when you're tired, bummed out, self-conscious, or sick, it's a cliché to don that sweater/sack dress/boyfriend jean that you can disappear into. Still, we know those days and those pieces are completely necessary. But, don't discount your biggies when you're feeling energetic, jazzed, confident, and happy, too.
The difference between sad-and-baggy and rad-and-baggy is all about what you're wearing your oversized pieces with. Click through to see the six most common oversized pieces, and our ways to bring them out of your doldrum-day wardrobe.

The Oversized Suit
There's something so cool about an oversized suit, and you don't have to be model-tall to pull it off. It's all about knowing where to strategically pare back. If you're shorter, try for a crop just at the ankle (taller girls can more easily get away with longer lengths). Keep the waist trim and the top cropped so you're not swimming in fabric from head to floor. Also, opt for a neutral color; anything bigger and brighter can end up looking like pajamas. Keep your accessories on the sleek side, but use this as the place to go wild with color.
Tome top, jacket, and pants; Karen Walker shoes.
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Cole Haan, $98.00, available at AmazonPHOTOGRAPHED BY LANDON NORDEMAN.
The Oversized Pant
If you're wearing big palazzo-style pants, you've probably also reached for your tallest heels and a tiny cropped top. While that look always works, we're here to propose another. Flat sneakers and a long, sinewy top that reaches just below your butt create a super-lean silhouette.
Suno T-shirt, Marissa Webb cropped top, Acne jacket.
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Rodebjer, $625.00, available at RodebjerBuilding Block, $495.00, available at Building Blockadidas, $65.00, available at adidasPHOTOGRAPHED BY LANDON NORDEMAN.
The Oversized Sweater
Your go-to move might have been to wear your big, chunky sweaters in oatmeal colors with skinny jeans and booties. But, this time around, wear yours with a loud-colored trouser (even better if it's oversized, too).
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Joe Fresh, $16.00, available at Joe FreshWilfred, $165.00, available at AritziaH&M, $299.00, available at H&MDKNY, $195.00, available at DKNYPHOTOGRAPHED BY LANDON NORDEMAN.
The Oversized Cardigan
These long, to-the-knee cardigans are the real-life version of the season's runway-hit duster sweaters. Treat yours like a dress by buttoning the bottom and cinching the waist with a belt. If it's a substantial enough knit, you can wear it over a chunky sweater, too.
Sonia by Sonia Rykiel cardigan and belt.
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Demylee, $140.00, available at DemyleePatagonia, $22.00, available at PatagoniaPHOTOGRAPHED BY LANDON NORDEMAN.
The Oversized Coat
If you're going for a big coat, go for a big pant, too. This big-on-big match-up looks surprisingly modern — just make sure your accessories are on the more delicate side.
Preen trench, Nonoo sweater, Kenzo pants.
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PHOTOGRAPHED BY LANDON NORDEMAN.
The Oversized Scarf
Silly, muppet-limb-style scarves are one of our favorite trends this season, and to wear yours well requires a sense of humor. Don it with your favorite loud sweater, on-trend jeans, and fun pair of shoes — and that's it. If you're layering correctly, you should be toasty enough to wear this look outside, too. (Be smart, here, we don't want anyone suffering frostbite in the name of fashion.)
Michael Kors scarf, Eugenia Kim shoes.
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PHOTOGRAPHED BY LANDON NORDEMAN.Like what you see? How about some more R29 goodness, right here?
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