10 Ways You Haven’t Thought Of To Style An Oversized Sweater

10 Ways You Haven’t Thought Of To Style An Oversized Sweater
Photo: Adobe; iMaxTree. DESIGN: Cierra Miller/STYLECASTER.

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When I’m feeling a little tired of my closet, the question is not a matter of what to buy but how to style. Am I the Shakespeare of fashion? Probably not. But like great literature, there are a few closet staples that will never (and I mean never) go out of style. Amongst the critically acclaimed white Converse, leather jackets and black blazers of the fashion world, we have the oversized sweater. As the bitter cold of winter falls upon us, the question remains: How to style an oversized sweater

Maybe you found your oversized sweater vintage shopping in your hometown and wear it with fond memories of the hypothetical grandpa that once owned it. Or perhaps you saved money for months to buy the Instagram famous Balenciaga logo sweater. And finally, I promise I won’t tell if you’re less like Romeo and more like Jake Gyllenhaal with the stolen chunky knit of an ex-lover to keep you warm during long, lonely nights (because let’s be real, it doesn’t remind you of innocence). 

While the way we wear these iconic pieces may come and go with trend cycles and seasons, the items themselves remain timeless because there are endless ways to style them. Whether you prefer a neutral fisherman knit or a colorful pattern, a wide belt or knee-high boots should be at your beck and call to pair with it. If you don’t already own an oversized sweater, I would recommend purchasing a high-quality style and challenging yourself to wear it at least a few times a season for years to come. 

Do not fret, I skipped the spark notes and went straight to street style to provide a sonnet-worthy sweater styling roundup. These 10 ways to style an oversized sweater are guaranteed to stun at your next Socratic seminar and in true trend-setting fashion, everyone will simply say “I agree”.

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With a Maxi Dress

The dramatic proportions of a chunky knit sweater and a floor-sweeping dress instantly look high fashion. I love this combination during the winter since it keeps your whole body covered and you can easily hide additional layers underneath (hello fleece-lined leggings).

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With Combat Boots

Combat boots are the universal outfit maximizer and an oversized sweater is no exception. Bonus points if you find a delicate knit (like the crochet one above) to off-set the grunge of the combat boots.

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With Statement Shades

The beauty of an oversized sweater is in its simplicity. Let the sweater give “I’m just running to the farmer’s market” chic and add statement sunglasses as an accessory. Every time you switch the shades, you have a full new look!

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With Bright Pants

A head-to-toe colorful look works year round. Treat a patterned sweater like it is a part of a set with coordinating pants.

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With a Collared Shirt Underneath

Take inspiration from your dad’s closet and layer a collared shirt underneath an oversized sweater. The large fit will keep the look casual so you don’t look like you’re attending private school or a day at your dad’s office.

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With a Chunky Belt

Create an exaggerated silhouette by throwing a chunky belt over the sweater. The more fabric that hangs over the top, the better.

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With a Monochromatic Color Scheme

Sweaters come in every color imaginable so pick a few your favorites and start the hunt for matching bottoms. Think of the pairing as a cozy and casual alternative to wearing a suit.

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With Knee High Boots

If your sweater is really oversized, skip pants or a skirt altogether and let a pair of knee high boots meet you halfway. This is a great look for a night out.

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With Color-Blocked Accents

Forget matching your belt to your shoes, match you sweater to your eyeshadow, heels and anywhere else you want a pop of color.

STYLECASTER | How To Style Oversized Sweater

iMaxTree.

With a Bow

Similar to a collared shirt, a shirt with a large bow looks amazing peering out from underneath a sweater. I love the combo of this letterman sweater with the bow because it is taking an athletic look and adding contrasting glam.

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