How to wear your oversized sweaters with anything in your closet– and how to shop for more pieces to pair with them too!

Getting into the colder months, my favorite pieces to reach for are the sweaters that swallow me whole and sit on the top shelf of my closet all year round.

Dressed up or dressed down, there’s nothing you can’t do with an oversized sweater and I should know, I have tons of them!

Four girls wearing oversized sweaters

If you’re here because you searched up, “how to wear an oversized sweater,” you’re in the right place. We aren’t just talking cute winter cardigan outfits here, although I love those as well.

It can be daunting to make the switch from fitted and cropped to long and large knitwear, but there’s something chic and fashionable about embracing the cottage core winter outfit trend, even if you’re accustomed to thinking it looks sloppy.

Playing with silhouettes and outfit themes are some of the most fashion forward tricks you can play to turn something from a casual and relaxed look to something that’s more fashion forward.

Expert Tip: An example of this is that I love to wear a more earthy oversized sweater with loose leather pants– now it’s something that’s visually interesting!

Jeans with an oversized sweater, three different ways and styling

How To Wear Oversized Sweaters With Jeans

Jeans might be the hardest pants to pair an oversized sweater with, because of all the different ways that jeans can possibly fit and flatter your body.

Skinny jeans are a good go to, and while they should always be a staple in your closet, we aren’t exactly in the year of the skinny jean.

Here are some ideas for pairing your jeans with an oversized sweater:

1. Cropped Straight Leg

These jeans go perfectly for a cute casual look. They’re not too fitted, but they’re not baggy. A pair that has just the right fit is the perfect pair to wear with an oversized sweater.

2. Contrasting Jeans

Using a jean that contrasts quite a bit keeps it from feeling like you’re being swallowed by the sweater or by the look as a whole.

3. Embrace The Slouch

The slouchiness of this outfit is what makes it work. It’s cohesive here.

With Leggings

Leggings are easy– especially with a chunky boot. This is my personal winter uniform. Oversized sweater, leggings, and a really cool boot.

4. Leather Leggings

Our girl on the left has the right idea: A bright fun color with a leather legging is the perfect way to keep that silhouette new and fresh.

5. Keep It Simple

This is a staple in all of our closets, we don’t have to overthink it! This is perfect.

A girl wearing an oversized sweater with a mini skirt

With Shorts

Transitional seasons are tough when it’s chilly at night and in the morning, but nice and a little bit warm in the afternoon. If you need a good inbetween, I love a good oversized sweater with shorts.

6. Peek-A-Boo

This one is with a skirt, but the visual representation still stands. With a little bit of a peek-out, a pair of shorts can be the perfect addition to the oversized look.

7. With Tights

Layer some tights under your shorts to give it the look like you’re wearing a dress. Elevate the whole look with some sheer black tights or some fleece lined tights.

8. Cross Body Bag

Throw on a cross body bag to add some interest to your look and hide your shorts with your sweater.

How To Wear Oversized Sweaters Without Looking Fat

If you’re not used to this look, I know it can feel incredibly unflattering to wear a sweater that’s way larger than your actual size.

But the truth is that it’s all a mind game. It comes down to the visuals, and where the sweater hits you. Does it end at your largest point? Is it an unflattering color for you? Finding the right one will solve all of your problems.

9. French Tucked

This is the perfect example of an oversized sweater French tucked into jeans. This is a great way to add some shape back into your outfit if that’s how you prefer to wear it.

10. As A Dress

Wearing it as a dress highlights your legs a little bit and keeps the look grounded on what your proportions are. A cute way to make it more wintery is with knee high socks.

11. Even More Layers

Adding even more layers will ensure that you simply look cozy and warm, not bulky.

Two girls in oversized cable knit sweaters

Oversized Cable Knit Sweaters

Some of the prettiest and most clean looking sweaters are your cable knits. Starting with these oversized cable knit sweaters is going to show you a whole new world of clean looking oversized style.

13. Linen Skirt

I love this combination, the texture with the soft flowing of the skirt, it’s a stunning outfit all together.

14. With Uggs

This is the PERFECT fall/winter look… Comfortable jeans and platform Uggs (these are the ones I just bought!) with an oversized cable knit sweater. How cozy.

15. Keep It Preppy

With a bow. This is the cutest look and very on trend with the preppy outfit style for 2024.

Are Oversized Sweaters In Style In 2024?

In 2023 and as we roll into 2024, yes, oversized sweaters are very much in fashion. The styles currently are very visually interesting and that usually means that either our pants or our tops are oversized, if not both.

Playing with menswear and tailored pieces in an oversized way has never been more in fashion, so have some fun with these concepts! Even if it’s just adding one of these kinds of pieces to your favorite pair of jeans.

The size and fits of our sweaters in style go in and out every year, but does anyone actually get rid of their sweaters? Of any size? Not really, we just find new ways to wear and style them.

How To Play With Silhouettes

I touched on silhouettes a little bit earlier in this post, but it’s my personal favorite part of styling and dressing to play around with to create cool outfits.

I adore a slouchy jean with a more fitted top or vice versa, and sometimes even baggy on baggy if something cool and tailored like a blazer is involved.

If your mind goes straight to assuming that something with a baggy or slouchy silhouette is sloppy and unpresentable, this kind of sweater that we’re diving into today is a really great introduction to starting to see it a little differently. It can be quite chic and fashion forward to break some of the more traditional rules and understandings of how fits work.

Play around, and you might make some outfits you really love with new silhouettes!

As you’re jumping on the oversized jumper train, I hope you’ve found some great and foundational outfit ideas here to help you change it up a bit within your own wardrobe… and beyond. Tell me which style is your favorite of them all.

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