8 Tips On How To Wear Oversized Clothes Without Looking Awkward

If you read the title of this post and thought, “Simple: Put oversized clothing item on your body, proceed with life, done,” then, well, that’s fair. There isn’t necessarily a science to wearing oversized clothes, but hear me out…

Oversized clothes are definitely cute and comfy, but they can be a little intimidating. Usually, when I see oversized clothing in ads, style-based Instagram/Tumblr accounts, the person wearing it is pretty thin. The oversized shirt hanging oh so loosely on their body is coupled with some sort of aspirational carefree vibe. “Look at how small I look in this massive top, tee hee.”


As someone who is tall, curvy, has a wide upper body, big boobs, and a little bit of a tummy, I–tee hee–can’t relate.

Sometimes, a top that’s sold to me as oversized isn’t that oversized at all, or it ends up making me look like a shapeless sack of potatoes. Now, that’s fine if I want to go for the shapeless sack of potatoes look, but that’s usually not on my agenda. Luckily, there are a few ways to wear oversized clothes that look awesome on every body type instead of vaguely awkward on anyone over a size four.  So, without further ado, check out these eight tips on rocking oversized clothes. Who knows, if you’ve been adverse to rocking oversized clothes before, you might get inspired to give ’em a try.

Tuck In An Oversized Shirt Or Sweater

This is my personal favorite look for an oversized shirt or sweater: Tuck that bad boy into your waistband. It still shows off the bagginess--especially if you leave a little untucked--without looking like you're swimming in fabric.

Buy this sweater at ASOS for $31

Throw A Belt Into The Mix To Avoid Looking Shapeless

Plenty of people love wearing oversized dresses, and others love the idea of wearing oversized dresses, but aren't crazy about the end result. I'm often in that latter category, especially if we're talking about shapeless shift dresses. I'm not at all petite, and I often feel like I look like a big ol' walkin' rectangle if I'm wearing an oversized dress. But finding a fix is easy: Throw on a belt. A belt puts emphasis on my body shape instead of the shape of the dress itself. You can find cool belts in all sorts of shapes, sizes, and styles, so if you have a shapeless oversized sweater hanging in your closet, dying to be worn, you know what to do.

Buy this belt at ASOS for $22

Pair With Chunky Shoes With An Oversized Sweater

You might want to pair an oversized sweater with something a little more toned down, like a basic pair of skinny jeans. That's all well and good, but you can find some really fun balance in your look if you throw a pair of chunky boots into the mix. It also draws the eye away from the intensity of your oversized sweater without overshadowing it. Frankly, it's just a cute look that anyone and everyone can pull off.

Buy this sweater at UNIF for $88

Play With Lengths

It's really fun to mess around with contrasting lengths when you're rocking something oversized, especially an oversized coat. Consider pairing an oversized coat with a mini skirt, or a cropped oversized jacket with a jumpsuit or maxi dress.

Buy it at ASOS for $173

Don't Assume That An Oversized Shirt Will Actually Have An Oversized Fit On You

So, a lot of retailers will try to dupe you into thinking that a one size only oversized top will be oversized on everybody. The problem is, uh, not everybody is the same size. The top to the left is a perfect example: I bought it and, yes, while it's loose, it's definitely super oversized on my frame (thanks, boobs). So, if you can, try before you buy or compare the fit of an oversized item to the body measurements of the model wearing them (many online retailers provide that information now).

Buy this shirt at American Apparel for $22

When In Doubt: Leggings

I don't care if I get hate for this: Leggings can totally be worn as pants. If you want even a smidgen of proof, just think about how killer a basic pair of leggings and an oversized shirt or sweater look together. So, when in doubt about a cool way to rock your favorite oversized top, just throw on some leggings, shoes of your choice, and keep it movin'.

Buy this sweater at Zara for $22.90

Don't Be Afraid Of Novelty

Oversized clothing definitely stands out, so why not just go all in? You can have the most fun with oversized coats, jackets, and sweaters that make a serious statement, whether in terms of color or an eye catching print. To the left is a photo of me rocking this massive (AND I MEAN MASSIVE) leopard print coat that straight up makes me look like a rapper from the '90s. It's so OTT, but so fun; a regularly fitting leopard coat just won't give off the same vibes.


Find Interesting Elements For More Pizzaz

A plain oversized top can be a little boring, so you might be more inspired to wear an oversized top or coat if it's a little more visually interesting. Check out oversized blouses with cool sleeves--like batwing or dolman sleeves--or even ones that have fool cut outs, mesh panels, etc.

Buy this blouse at ASOS for $49

Do you like wearing oversized clothes or do you think they tend to look awkward? Tell us in the comments!

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