5 Styling Tips on How to Wear Oversized Sweaters

oversized sweater

Top: Ottoman Slouchy Tunic, more colors here | Jeans: Maternity Skinny Jeans, non-maternity here | Bag: Leopard Clutch, similar here | Hat: Wool Fedora, similar | Shoes: Newbury Boots, also here and similar

I’ve long been a fan of the oversized sweater. I think that living somewhere with brutal winters will do that to you. One winter in Chicago and I was over the cute, thin, fitted sweaters. They simply weren’t warm or cozy enough. Now my closet is filled with a good mix, but most of my sweaters lean towards the oversized side. There’s a good reason for it too. They’re the perfect thing to wear when it’s freezing outside and you just want to be warm, cozy, but still look cute. Oversized pieces can easily go from looking cool to frumpy, so I’ve put together a few pointers on how to wear them the right way.

How to Style Oversized Sweater Outfits

1. Tailored Bottoms

When it comes to wearing any boxy or oversized top, a good rule of thumb is to keep the bottom half of you looking more tailored. It keeps your look balanced and gives you that effortlessly chic look. Jeans are my go-to, so I stick to well-fitting skinny jeans to give shape to my legs, but tailored ankle pants like these would look great and be perfect for the office too. I love that both of these styles are straight or tapered at the ankle giving shape to the bottom half of you and making your legs look longer.

Ankle Pants & Skinny Jeans


 

fedora hat outfit

oversized sweater outfit

red sweater fashion
fall fedora hat outfit

2. Consider Your Height

Oversized sweaters typically fall into two categories. One being a boxy, but shorter oversized fit, and two being a more straight, but longer fit—like the one I’m wearing here. I love both, but depending on your height and body shape, one might be better for you than the others. If you’re shorter, I’d opt for a shorter oversized sweater and then follow tip number three. Sweaters that are too long can make your legs look shorter, which might be great if you’re super tall, but not ideal if you’re short.

3. Tuck It

When in doubt, tuck the front of your sweater into your jeans or pants. It’s a little tougher with a bump, but the front tuck is my signature move to making oversized tops look more stylish and intentional. It also helps to elongate your legs, so if you’re on the short side, definitely try this little trick!

fall booties outfit

fall outfit ideas

4. Frumpy vs. Stylish

There’s a fine line to walk with big sweaters and you don’t want to fall on the frumpy side. Instead of just ordering any sweater a size or two up, pick sweaters that are designed to be oversized. Simply ordering up a few sizes will give you an oversized look, but sleeves that are too long and awkward will make it look like you ordered the wrong size. Sweaters that are designed to be oversized will fit your arms and shoulders appropriately leaving you looking styled, not frumpy.

Oversized Sweaters


 

red sweater outfit
booties

pregnancy style

5. Wear Heels

If you’re worried about looking too casual, simply add a pump or heeled bootie to elevate the look. It doesn’t have to be fancy—my look is still super casual, but it elongates your legs and adds some edge to your look. If you really hate heels, opt for flats with a pointy toe that will give the illusion of longer legs too.

Do you love a good oversized sweater for fall and winter? What tips do you have for styling them the right?

BTW, how to style a fedora hat, and two fall colors that you need asap.

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