14+ Sweatshirt Outfits That Prove This Piece Isn’t Just for Sport

These chic sweatshirt outfits will show you how to take this wardrobe staple beyond working out, including oversized sweatshirt outfit ideas, black sweatshirt outfit looks, cropped sweatshirt outfit ideas, and oversized hoodie outfit ideas!

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overhead selfie of a woman in a houndstooth blazer over a grey sweatshirt, jeans, and sneakers

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How do you style a sweatshirt in 2023?

Sweatshirts as a wardrobe staple won’t be any different in 2023, and we will continue to see them worn in chic ways beyond working out. There are many ways to style a sweatshirt including wearing it with leisurewear like leggings, joggers, and sweatpants. Or, you can dress up a sweatshirt with jeans, wide-leg trousers, leather pants, or a midi skirt, or wear one under a blazer for a business casual vibe

Even if you are at the office 9-5, every day of the week, you can still find many opportunities to sport a classic sweatshirt, even at work.

Chic Sweatshirt Outfits

We’ve scoured the fashion world and stalked our fave style influencers to share the top sweatshirt outfits that we know you’ll love too! There are sporty looks, casual outfits, and a couple of dressier options, so read on to be inspired. 

tennis street chic

woman wearing a faded black graphic sweatshirt with a black mini skirt and chunky black sandals

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This look is cute and casual for spring or summer. A tennis skirt is the perfect athletic piece to add a feminine feel to a sweatshirt outfit.

We love the combo of the graphic Anine Bing sweatshirt, the black tennis skirt (or skort), and the chunky double-strap sandals. The hat keeps the outfit looking laid-back, but the leather YSL crossbody elevates the whole look. 

This outfit can easily be recreated with any crewneck sweatshirt, tennis skirt or skort, and chunky sandals. You don’t need a designer bag, just opt for a sleek black leather bag with a minimal design.  

ode to the oversized denim jacket

woman wearing an oversized denim jacket over a white crewneck sweatshirt with faded black jeans and black leather ankle boots

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The beauty of an oversized denim jacket is that it’s roomy enough to layer over a chunky sweatshirt. This outfit has a laid-back feel but is made slightly dressier with heeled ankle boots and gold jewelry. 

If you aren’t in the mood for sneakers, but still want to feel comfortable in a cozy sweatshirt, here’s what to do. Put on your favorite jeans and add an oversized denim jacket and black ankle boots to bring in that modern aesthetic. 

the matching sweatsuit, elevated

woman wearing a matching grey sweatshirt and sweatpants with a long ivory wool coat over, and white sneakers

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You can never go wrong with a matching sweatsuit. It’s the quintessential cozy outfit that looks more elevated when the pieces come in a set. 

This minimal grey set from Anine Bing is stylish and chic, paired with a soft oversized neutral coat, suede bag, statement sunglasses, and classic white sneakers. The perfect coffee run outfit for the weekend. 

quarter-zip sweatshirt + leather pants

woman wearing a light grey half zip sweatshirt with leather pants and white sneakers

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Who doesn’t love a basic good quarter-zip or half-zip sweatshirt that gives that vintage varsity aesthetic? This style of sweatshirt looks great with the unexpected, black leather pants. 

The result is a laid-back look with an edgy feel. And, the New Balance sneakers are the perfect finish to the outfit. You can easily wear this running errands, out to brunch, or on a casual date. 

blazer + biker shorts combo

asian woman wearing a hoodie under a blazer with black shorts and sneakers

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A blazer, hoodie, and biker shorts are a match made in heaven. We’ve been seeing this outfit combination everywhere over the past year and we love the sporty-chic aesthetic it gives. 

This sweatshirt outfit has an elevated appeal with a mix of neutral colors (always a timeless choice), and the blazer makes the feel polished and sophisticated. 

put a vest on it

woman wearing a padded leather vest over a tan sweatshirt with black jeans and black ankle boots

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Next on the list of sweatshirt outfits is one of our favorites. This whole outfit has a high-fashion feel and shows how a classic sweatshirt can easily be worn with other wardrobe staples. 

The vest is definitely the star of the outfit and looks great over the tan crewneck sweatshirt. Black cropped bootcut jeans keep the look fresh and modern, while black leather boots anchor the whole outfit. 

Oversized Sweatshirt Outfit Ideas

Go big or go home, right? Oversized sweatshirts are super popular, especially among fans of the ‘baddie’ aesthetic. But, even if your style is relatively refined, you can still find a way to sport an oversized sweatshirt outfit. 

Check out our favorite looks to copy below. 

oversized sweatshirt, gone grunge

woman wearing an oversized sweatshirt with black shorts, black sheer tights, and combat boots

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There’s something so appealing about this grunge-inspired outfit that combines an oversized sweatshirt with leather shorts, sheer tights, and combat boots. While this look isn’t for everyone, the grunge vibe has made a comeback in the last couple of years, but in a slightly more refined way. 

We love how the sweatshirt has a youthful feel, but the tights and combat boots add that grungy edge. Wear this outfit to a concert, shopping, or out with friends at the best coffee shop.

oversized sweatshirt + turtleneck

woman wearing a turtleneck under a crewneck sweatshirt with biking shorts

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Leave it to style icon Anine Bing (queen of the sweatshirt) to give us a perfectly elevated oversized sweatshirt outfit. If you live and breathe fashion, there’s a good chance you already have an Anine Bing sweatshirt in your closet… or a few! 

We love how Anine has styled her sweatshirt with a turtleneck underneath, long biker shorts, a chic handbag, cat-eye sunnies, and gold jewelry. The look is sporty, yet polished, and dripping with coolness. 

the wellness junkie look

woman wearing a crewneck white sweatshirt with black leggings, white socks, and sneakers

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You just finished your morning yoga class, and now taking a brisk walk to your fave juice bar for a green smoothie, with collagen. That’s exactly what this chic sweatshirt outfit gives, and we’re here for it. 

The oversized sweatshirt has a varsity feel and the leggings keep the outfit looking clean and classic. The white socks and sneakers combo finishes the look perfectly…and let’s not forget the cotton tote for a yoga mat. 

classic black sweatshirt outfit

woman wearing a black sweatshirt over a white collared button down shirt with leather pants and white sneakers

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Every woman needs a classic black sweater or sweatshirt in her closet. While sweaters usually have more of a polished feel, this outfit shows how a black sweatshirt paired with other timeless pieces can create a refined appearance. 

In other words, you can easily dress up a sweatshirt! This leads us to our next question…

How do you dress up a sweatshirt?

A sweatshirt can be easily dressed up by pairing it with more formal pieces like tailored trousers, leather pants, a midi skirt, a blazer, or a trench coat. For a dressed-up look, make sure the sweatshirt is the most casual piece in your entire outfit.

Add heels or ankle boots to enhance your outfit even more. And, don’t forget to accessorize with elevated pieces like a leather shoulder bag or clutch and elegant jewelry. 

the dressy sweatshirt outfit

woman wearing a crewneck tan sweatshirt over a black midi slip skirt and black ankle boots

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Here’s how to take a basic sweatshirt and make it fancy. When wearing a sweatshirt for a more formal occasion, make sure you choose one that is a solid color (neutral is always a safe choice) with a more tailored fit (pictured is the Totême Eurora silk terry sweatshirt, which is currently sold out so we’ve provided alternatives linked above!).

We love the look of this camel crewneck sweatshirt with a sexy black midi-length slip skirt and black leather ankle boots. The black leather shoulder bag and gold jewelry add to the outfit, making it a perfect option for date night or a broadway show

cropped sweatshirt outfit

woman wearing a matching cropped sweatshirt and shorts set with white sneakers and a blue ball cap

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If you have the midriff (or the confidence) to sport a cropped sweatshirt outfit, here’s a great way to do it. Find a cute matching set with shorts and throw on a pair of sneakers and a baseball cap. 

This outfit is a comfortable and playful option for the summer. Or, wear it on vacation when you plan to head to the pool after grabbing breakfast and an iced coffee. 

You can also easily swap the sweat shorts for biking shorts, leggings, or jeans. 

Are hoodies in style 2023?

Hoodies are a piece that will definitely still be in style for 2023. Oversized hoodies in particular have been very popular over the last couple of years and will be sticking around. We will continue to see hoodies styled with leisurewear, and also with business casual pieces like wide-leg trousers, leather pants, and midi skirts.  

Oversized Hoodie Outfit Ideas

If you are looking for chic ways to wear a hoodie, be inspired by these looks below that feature the oversized style we love. 

simple oversized hoodie outfit

black woman wearing an oversized grey hoodie with loose long jeans and white sneakers

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The first oversized hoodie outfit is effortless, simple, and cute. Grab your favorite oversized hoodie and fold it under, add some loose-fit jeans, and put on a pair of chunky sneakers to balance out the hoodie. 

This outfit has major Y2K vibes and is wearable for any casual activity. Coffee run? Yep. Dog walk in the park? You bet. Farmer’s market stroll? Of course. 

oversized hoodie off the runway

woman wearing an oversized hoodie with cream leather leggings and white ankle boots

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Here’s an oversized hoodie outfit that has a totally different feel. The hoodie is casual, yet easily elevated with cream leather leggings and white leather sock boots. 

The Chanel purse takes the whole outfit up another notch (but you don’t need one to recreate this look), and the oversized sunglasses complement the hoodie perfectly. 

If you are looking for a sweatshirt outfit that makes a statement, this is definitely one to try. 

trench coat + oversized hoodie

stylish black woman wearing a grey trench coat over grey hoodie with green jogger pants and white pumps

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Last on the list of sweatshirt outfits is a fun and playful look we love.

The oversized hoodie is the perfect style to wear under the oversized trench coat for a modern look. We love this sporty, yet feminine outfit that combines casual pieces with dressy heels for a touch of glam. 

The grey, green, and pop of white make for an eye-catching color combination. But, you can just as easily go with a black hoodie, tan trench coat, black trousers, and a neutral pump for a more subtle take on this outfit. 

What do you wear with a sweatshirt?

A sweatshirt is a surprisingly versatile piece that can look excellent as part of both casual and dressier outfits. Here are just a few ways you can style a sweatshirt in a modern and chic way:

  • with jeans and classic sneakers
  • under a blazer with tailored trousers 
  • with a midi skirt and ankle boots
  • with leggings or biking shorts and trainers
  • under a trench or wool coat
  • with matching sweatpants or joggers
  • with leather pants or leggings

Creating chic sweatshirt outfits is easy when you know how to style them. We hope you’ve been inspired by this post and have discovered new ways to style your crewneck  sweatshirt, oversized hoodie, or cropped sweatshirt. 


More Style Guides You’ll Love:

16+ Chic Cozy Outfits That You Can Easily Wear On The Go

16+ New Balance Outfit Ideas You’ll Love in 2023

15+ Baddie Winter Outfits for Next-Level Aesthetic

15+ Coffee Date Outfit Ideas That Are Classy & Casual


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