18 Super Cute Ways to Style Oversized Sweatshirts

Here’s what you should be wearing with your oversized sweatshirts!

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Oversized sweatshirt photo from Princess Polly
Princess Polly

One of my favorite things to wear when I want to be cozy is an oversized sweatshirt.

However, it can get old wearing your same sweatshirt and jeans combo over and over. That’s where today’s post comes in.

Below, I’ve rounded up 18 cute outfits with oversized sweatshirts, with vibes ranging from chill to dressy. Check them out for some fresh outfit inspo.

Cute Oversized Sweatshirt Outfits

1. Pleated Midi Skirt

You may not have thought of pairing your favorite oversized sweatshirt with a skirt before, however, the look is so cute, especially if you choose a pleated skirt.

What is also fun about wearing a pleated midi skirt with an oversized sweatshirt is you can also wear some fun shoes to complete the outfit!

For example, if you want to really make your oversized sweatshirt outfit stand out, pair it with some boots or fancier shoes like the loafers seen above.

2. Plaid Skirt

If you want to go for more sophisticated vibes with your oversized sweatshirt outfits, I recommend adding a plaid skirt!

You can pair a plaid skirt with an oversized sweatshirt for a more sophisticated vibe if that is the type of style that you are going for.

And, what’s great about this type of look it will not only look good when paired with fancier shoes but also with casual sneakers for a chill outfit.

3. Track Pants

The ultimate chill outfit with an oversized sweatshirt is a sweatpant and sweatshirt combo!

Track pants along with a matching oversized sweatshirt may be just the everyday outfit you need for the winter time to keep you comfy and warm.

And definitely pair this look with some cute sneakers for the ultimate everyday comfy outfit.

4. Biker Shorts

Another great go-to everyday outfit if you love wearing oversized sweatshirts is pairing a sweatshirt with biker shorts!

Biker shorts paired with an oversized sweatshirt is one of my favorite everyday outfits when it is a bit chillier outside, but I still want to wear shorts.

I love this look with Adidas Sambas as shown above, but any sneaker would work.

5. Denim Shorts

If you are going for something comfy and easy for running errands, I recommend wearing oversized sweatshirts with denim shorts.

This will give you the ultimate comfy outfit for whenever you are running errands or hanging out with friends.

6. Cargo Sweatpants

For those of us who like to wear comfy outfits for everyday activities, then you should try pairing an oversized sweatshirt with cargo sweatpants.

This will not only give you a comfy outfit for your everyday looks, but also the cargo sweatpants will add a trendy clothing item to your look to make sure you still look stylish.

7. Denim Skirt

Longer skirts have been coming back in style, such as this denim skirt, and when paired with an oversized sweatshirt, it will give you a sophisticated and stylish look.

So, if you have been interested in trying out this skirt trend, I recommend pairing it with one of your favorite oversized sweatshirts to get a super cute look.

8. Joggers

Another great outfit for everyday looks would be an oversized sweatshirt and joggers set like this one!

White Fox sweats are super popular right now and they’re so comfy as well.

And what’s great about this look is you can easily make it look trendy by adding some accessories and trendy sneakers.

9. Lace Pants

You might not think to pair your sweatshirt with lace pants, but the look is actually so cute!

Lace is popular right now, so you will definitely look trendy in this outfit no matter where the day takes you.

Just make sure to finish this look with some trendy boots like the platform ones seen above.

10. Parachute Pants

Another in-style item that you should consider styling with your oversized sweatshirt is parachute pants!

Parachute pants have been very trendy recently, which makes them a great item to add to your oversized sweatshirt looks if you want to be comfy but also in style.

So, if you are interested in achieving this type of look, check out these parachute pants to create a stylish look for everyday outfits.

11. Jeans

Obviously, a go-to clothing item that looks super cute when styled with oversized sweatshirts is jeans!

You can also make this outfit look more trendy and edgy with baggy jeans and a cute oversized sweatshirt.

And, to add something fun to this outfit, you can pair it with chunky boots.

12. Camo Pants

If you trying to put together a more casual outfit that you can wear with an oversized sweatshirt, these camo pants may be just what you need!

Camouflage pants like these will give you a more casual look when paired with an oversized sweatshirt.

And, to complete this casual look, add a cute pair of Ugg boots, which are also very trendy right now.

13. Pinstripe Pants

Pinstripe pants are also another trendy type of clothing item that will look super cool when paired with an oversized sweatshirt.

This type of look can be worn for your everyday looks if you want something comfy and trendy, or you can also use this look to give you more of a classy vibe when paired with heels.

14. Khaki Pants

For a cool and casual look that you can create with an oversized sweatshirt, I recommend pairing it with khaki pants like these.

These khaki pants, when paired with an oversized sweatshirt and some sneakers, will give you a trendy look that you can wear for your everyday activities, whether it’s running errands or hanging out with friends.

15. Mini Skort

If you want to add a girly vibe to your oversized sweatshirt outfits, I recommend going for a look with a mini skort.

A mini skort like this one will look adorable when paired with any oversized sweatshirt, and I love how the skort and sweatshirt match in color.

Definitely try this outfit if you want something feminine and trendy to wear this season.

16. Cargo Joggers

If you are more of a pants girl and are looking for pants other than jeans or sweatpants to pair with an oversized sweatshirt, try some cargo joggers like these!

Cargo joggers with an oversized sweatshirt can be worn for more casual occasions, such as a casual dinner with friends.

And, if you want to add something trendy to this look, you totally can with some chunky suede boots.

17. Mini Skirt

Mini skirts are also a great choice if you are looking for another type of girly look you can create with an oversized sweatshirt!

Mini skirts like this one, when paired with your favorite oversized sweatshirt, will give you a super cute look you can wear every day.

This is the perfect outfit if you are looking for something more girly to wear while doing your everyday activities!

18. Track Shorts

If you like wearing matching lounge sets, you might also be interested in this outfit! As opposed to sweats, track shorts look amazing with oversized sweatshirts.

So, if you like wearing matching sets for lounging but want something different than the usual sweatshirt and sweatpants lounge set, I recommend checking out a set like this one that has a super cute oversized sweatshirt with matching track shorts!

What are your favorite outfits with oversized sweatshirts?

What outfit idea from this list is your favorite? What oversized sweatshirts are your favorite?

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