The Chic Way To Wear Oversized Everything!

This article was last updated on April 16, 2022

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We don’t have to tell you how amazing oversized clothing is, in terms of coziness — we know you’d live your entire life in your too-big T-shirts and shorts if you never had to see another soul again. But, when it comes to chic and flattering lines? Oof — a baggy silhouette just isn’t the first thing that comes to mind. 

However, with the right balancing acts and some sneaky styling tips, you can get the best of both worlds. Ahead, we’ve laid out eight ways to wear fall’s larger-than-life trend and still keep things pretty — click through for the golden rules of going big!

Oversized Sweater

Oversized Sweater — Basic, single-colored (or even coloblocked) oversized sweaters offer an opportunity to wear your super-skinny printed jeans and leggings. Style them with basic boots and a supple, expensive-looking bag for a look that’s far from shlubby. 

Banjo & Matilda Sweater, $325, available at Net-a-Porter.

Oversized Cardigan

Oversized Cardigan — For a layered look that plays on this season’s dress-over-pants silhouette, belt an oversized cardigan over a crisp button-down and skinny jeans. 

GAR-DE Dryas Oversized Cardigan, $112.50 available at The Outnet; Photo: via ASOS.

Oversized Blazer

Oversized Blazer — Keep the ’80s out of a boxy, oversized blazer by wearing it with a shorter hemline and chunky heels. We like the look of a colored or printed blazer over a textured shift dress. 

Cut25 by Yigal Azrouel Clothing, $550, available at Shopbop.

Oversized Clutch

Oversized Clutch — Clutches bigger than an 8×11″ sheet of paper tend to look overwhelming in anything but a single color. Use one to balance out a dress that’s got an allover print. 

Aila Red Envelope Clutch, $316.26, available at My Wardrobe

Oversized Coat

Oversized Coat — A voluminous coat will instantly make you look smaller, so it’s important that your shoe has some height to it. To balance out the extra fabric, decorate your neck; either a pretty collar, scarf, or necklace will draw the eye upward. 

Acne Sasha Wool Coat, $900, available at La Garconne.

Oversized Skirt

Oversized Skirt — In a knee- or midi-length, an “oversized skirt” features a full A-line silhouette that calls for ’50s-chic shrunken sweaters and cardigans. Mix your color families (pastels and jewel tones, fluroscents and neutrals) for a modern spin. 

H&M Oversized Skirt, $49.95, available at H&M.

Oversized Waistcoat

Oversized Waistcoat — When it comes to an oversized vest, make sure that you’re wearing something underneath that peeks out beyond the hemline, unless you want it to seem like you’re going the no-pants route. A pair of slim-fit brocade trousers and a paper-thin T-shirt (or, when the temperatures drop more, a turtleneck) look incredibly chic. 

Zara Studio Waistcoat, $189, available at Zara.

Oversized Earrings

Oversized Earrings — To let your oversized earrings take center stage, keep your dress simple, forgo any other ostentatious jewelry, and carry a handbag that sits low on the body (either a clutch or something featuring a cross-body strap). 

Photo: Courtesy of Tory Burch.

Click HERE to read more from Refinery29.

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