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5 Must-Know Styling Tips on How to Wear Oversized Sweaters & Look Chic AF

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We are a big fan of the oversized sweater all through fall and winter. It’s the easiest outfit to pull together. Here’s how to make it look chic—no matter the occasion.

After just one midwest winter, I really grew to appreciate the oversized sweater. It’s now a staple in my closet and I don’t see that changing anytime soon, especially since we still live in a cold winter climate.

Oversized, chunky sweaters are cozy, comfortable, and feel effortlessly chic when worn correctly. They’re incredibly versatile throughout the winter too.

Dress them up with a pretty silk skirt or sleek trousers. Or, throw one on casually with a pair of you favorite jeans or leggings with sneakers to pick your kids up from school.

Oversized pieces can easily go from looking cool and effortless to frumpy, right? I’ve been guilty of throwing on an outfit that looked amazing in my head, only to find out that I look like I just rolled out of a dumpster.

So, I’m sharing a few pointers to keep your oversized sweater outfits looking sleek and stylish. Once you master these rules, you’ll feel confident wearing your oversized sweaters with just about anything.

How to Style Oversized Sweater Outfits Like a Pro

First up, let’s talk about oversized. This doesn’t have to mean massively huge and drowning you. In fact, I’d argue that would be exactly how to not wear an oversized sweater.

We want to aim for sweaters that are designed to be oversized and look like they were meant to be that way, not just like you purchased the wrong size. Now, let’s get into these styling tips!

1. Play with Proportions

turtleneck sweater outfit

When you’re wearing something bigger and oversized on top, you want to balance it out on bottom so your outfit feels purposeful and intentional. Skipping this tip can leave your whole oversized sweater outfit feeling out of balance and just off.

Tailored Bottoms

When the top is oversized and baggy, reaching for tailored, narrow-bottoms like skinny or straight jeans, or leggings—we love a good pair of faux leather leggings—easily keeps proportions balanced. This helps give shape to your lower half. You can take this look and dress it up or down depending on what shoes you pick.

For sweaters that are very oversized, opt for a pointed ballet flat or pointed boot that helps to elongate the leg and create more balance for your oversized top.

I know everyone is telling you to toss your skinny jeans, but I disagree. We might not be wearing them like we used to, but they still have a place. A pair of skinny jeans with an oversized sweater with boots—yes, please!

Wide Leg

3 ways to wear a black sweater

When pairing with a wider leg pant or bottom, you run the risk of looking frumpy. To avoid that, create some definition at the waist to give some visual interest and break up the fabric.

Right now, wider leg styles are trending like crazy, and you can still wear an oversized sweater with them, just make sure to create some definition at your waist to avoid looking all over lumpy!

Tuck part of your sweater into the front, and add a belt for something unique to break it up. Or try this new product I just heard of, Tucky, to tuck your sweater under without creating extra bulk from tucking.

You can also do this with slouchy boyfriend-style jeans, or a more tailored trousers with a wide leg. Personally, I love both. Throw and long coat over it and you’ve got a chic look that’s comfortable too.

When it comes to shoes, I love a heel with wider leg pants to show some ankle and add some height. But on the flip side, I also love them paired with a pair of sneakers for a cool, urban look. This is great for running errands, picking up the kids and still feeling like you’re pulled together!


black sweater and denim skirt

When it comes to skirts, I recommend you stick to the same rules as wide-leg pants if you’re wearing a wider, flowing skirts. Tuck or belt your sweater to create definition at your waist to create more shape.

For fitted skirts like the one above, tie a rubber band around a chunk of the fabric in the front and tuck it under your bra to create the illusion of a tuck, without the excess fabric bunching under your skirt. Or grab that same Tucky belt I mentioned earlier—it would work wonders!

2. Pick the Right Style for your Body

spanx faux leather leggings outfit

Oversized sweaters typically fall into two categories. One being a boxy, shorter oversized fit, and two being a more straight, but longer fit. I love both, but depending on your height and body shape, one might be better for you than the others.

If you’re shorter, opt for a shorter oversized sweater so it doesn’t hang too low on your thighs. When it’s too long, it makes your legs look shorter and makes your sweater look too big.

If you’re taller, opt for a longer sweater when wearing with pants, and wear shorter ones with skirts.

3. Master the Tuck

everlane sweater outfit

When in doubt, tuck the front of your sweater into your jeans or pants. This is a quick way to up-level your outfit and make it look way more sophisticated and chic. It’s also so simple—you don’t have to add any fancy accessories or anything.

The tuck helps to elongate your legs, so if you want the illusion of looking taller, definitely try this little trick. Start by tucking the whole front of your sweater in and gently pull it out until you get the look you want. You want a nice chunk of fabric draping over the front.

If it’s billowing out too much, you probably need a longer sweater. You can also try tucking the front end of your sweater under your bra. For shorter sweaters, this can be a fun way to show a peek of skin for an edgy look.

Lastly, skip the tuck if you’re wearing your oversized sweater with leggings.

4. Go Monochromatic

When in doubt, the quickest way to make your oversized sweater outfit look totally chic is to go monochromatic. You can do this with neutrals, which is always so classic and chic, or make a statement with bolder colors.

I love the bold look especially for the holidays. It’s such a fun and unique look that’s timeless and elegant.

When it comes to monochromatic outfits, don’t worry about matching the colors exactly. Slightly differing shades look amazing together. If you’re wearing neutrals, feel free to mix and match differing shades as well.

5. Layer with Coats & Jackets

sweater and jeans–casual outfit

To complete your look, layer a jacket or coat over your oversized sweater. There’s no set rules here except for that your coat or jacket should be big enough to fit your sweater underneath. There’s nothing more uncomfortable than forcing a thick sweater into a jacket that’s too small. You can’t move your arms and your coat will look awkward and ill-fitting.

For a more casual look, try out an oversized denim jacket like the one above. I love the layers for warm, but also visual interest. Best of all, you can probably recreate this exact look from things you already have in your closet.

I also love grabbing an oversized jacket to throw on over it. This works for more formal, dressy looks, as well as for more casual looks. It so simple, but totally works. A beautiful camel overcoat is a winter essential in my book.

More Oversized Sweater Outfit Ideas

This classic black and denim combo is timeless and will never go out of style. You might even have a white sweater, black ankle jeans and booties in your closet right now.

The perfect example of how to pair all of your different neutral tones together for a sophisticated outfit. We love the mix of textures in this outfit too.

Another monochromatic look with dark blue and brown flats. Such a fun way to wear blue in winter.

jeans with a grey sweater tank and green booties

Oversized sweater & pointed boots make this outfit both comfortable and stylish.

Cream on cream looks amazing in winter. I love how she paired white sneakers for a fun, sporty-look that anyone can pull off.

BTW, 3 pairs of trousers to add to your wardrobe, and the best simple gold jewelry—all under $15



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