18 Cool Sweatshirts And 6 Fun Ways To Style Them For Maximum Comfort

I am now of the opinion that a sweatshirt is the most versatile and useable piece of clothing in anyone’s wardrobe. Sure there are certain, fancier occasions when a sweatshirt would be a bit inappropriate but when styled right they can go from cuddling on the sofa to dining at a cool restaurant. I think I may have turned a corner on my sweatshirt philosophy once we were out of quarantine but not ready to let go of being in comfortable clothes 24/7. Plus there was/is a ton of incredible inspiration on the internet, for just anyone to see and try themselves! Also, a sweatshirt is the perfect layering piece that can easily move between all four seasons – especially now that there’s a solid chill in the air. Sweatshirts are a very important clothing item, ok? So today I have rounded up six easy ways to style your sweatshirts so you can be both comfy and cute. Right this way…


I love and have worn this look multiple times. You probably already own most of the pieces too. A fresh-looking hooded sweatshirt, leggings, your favorite sneakers, and an oversized long coat. A baseball hat and a cute purse for bonus points. Now, you can totally play with color but I think there is an inherent chicness to a neutral-toned “sporty” look.

Matching Set

Maybe you want to kick up the warmth and sportiness and go for a matching sweatshirt/sweatpant set but still wear an oversized coat. So it’s the same idea as before but this time you might want to go with a bolder shoes like boots or high-top sneakers. Since the pants are bulkier, a boot helps to visually balance out the look. It’s also nice when it’s really cold and snow might be imminent:) Also, notice that in both photos that their accessories are kinda fancy or on the trendier side. The trendy sunglasses and bag on the left and on Tracee (yes, we are on a first-name basis), a designer bag and a bold red lip.


Jeans and a sweatshirt are the other classic power couple and you can see why here. What makes these looks work is the fit of the sweatshirt. There are a little more fitted. I know the term “fitted” doesn’t scream comfort, but if you find the right cut and material, I promise it will be. Take a look at Blake Gifford sporting her college sweatshirt that’s fitted on her waist then paired with jeans and SUPER cute heels. Easy and super stylish. Then in the middle photo, Jeanne Damas is wearing high-waisted jeans with her sweatshirt tucked in in the front and styled with those cute suede boots. I would happily walk down the street in that look.

But of course, you can also just throw on a hoodie and an overcoat (with a cute bag) and be good to go.

Fun Pants

This is when things get more fun. Do you have really cool pants that you feel are only for dressier occasions? Hey, just throw on a cute sweatshirt and whatever shoes you’d like and you are all set! I think this outfit could work for so many different outings or events. Heck, if you work somewhere more creative or that lets you dress how you want (aka probably not corporate America), this is a perfect fall/winter work outfit too:)

Casual Suit

Speaking of the office, look at how incredibly cool and chic these suit looks are?? I really love that the sweatshirts are slightly oversized and work because everything else is structured and tailored. Also, the accessories are very good and help to elevate the outfit.

And finally the sweatshirt/skirt combo. I clearly couldn’t stop myself when picking inpso photo because there were too many good ones. Each of these are unique in their own way and goes from pretty casual to almost fancy. Do you see that shirt with the feathers?? So if you have a skirt you love but never wear, throw on the sweatshirt to dress it down and make it a fun casual look!

Feeling inspired?? I hope so because fashion should be fun and for me, this has been a really approachable way to play with a piece of clothing I’m usually trying to hide in. If you are in need of a sweatshirt, I’ve picked out 18 really great ones to get you started:)

1. Women’s Cropped Hoodie: I own this sweatshirt in four colors and I LOVE it. It’s perfectly cropped, very comfortable, and wildly affordable. 10/10.
2. The Track Oversized Crew: This looks like a great oversized yet structured option that has a lot of great reviews. And it comes in 3 other colors!
3. The Slouch Sweatshirt: Okay. I know this isn’t a cheap option but I know from personal experience it is a dream to wear. I bought a used one at this awesome clothing resale place near me and I wear it all of the time. If I had the budget to buy more new, I would.

1. Shawl Collar Henley Sweatshirt: How cute would this look with jeans or a bold pant?! That collar is really awesome.
2. Turtleneck Sweatshirt: This one also has a really cool collar that I feel you don’t see very often. It also comes in green!
3. (Re)sourced Fleece Button-Front Hoodie Sweatshirt: First off, this is one of my colors! I think it’s beautiful and is also technically a fleece so you know it’s warm. It also comes in cream if Merlot isn’t your cup of wine:)

1. Crosby Half Zip Pullover: This is one of Emily’s favorite sweatshirts and is the one she’s wearing in the opening photo. I know she loves the fit and the color. As Em has proven many a time, it’s easy to make look very cool:) It’s on my list!
2. Rivet & Thread Floral Turtleneck Sweatshirt: I really love this color and how versatile it is! I also love/prefer a loose hem (especially when I’m not feeling particularly great physically).
3. The Shrunken Sweatshirt: This is the less oversized sibling to the one I raved about above. My feelings are the same and someday I hope to own some. FYI the hems on these are “fitted” but soft and on the looser side which I really love.

1. Fuzzy Turtleneck Cropped Sweatshirt: This is not a color that I normally gravitate towards but in a sweatshirt that’s more casual, I really love it. This one looks super comfortable and is cropped which is a dream for my short body:)
2. Perfectly Oversized Cropped Crew: I am a sucker for a neon yellow and I love the cut and shape of this one!
3. Magic Rinse™ Relaxed Crewneck Sweatshirt: Emily told me that she saw this one in person and said it was awesome. Naturally, I needed to include it! It also comes in a bunch of other colors.

1. Woman Pullover: Fewer things are cooler than a great graphic sweatshirt. Personally, I prefer ones that are a bit more minimal and I’ve had my eye on this one for a while. Also, if you haven’t checked out Sammy B.’s designs I think you should right now:)
2. Sportswear Logo Crop Hoodie: This one has color but juuuust enough. I also love the cream and gray stripes!
3. Rec Room Sweatshirt: I think this one is just cool and looks really soft and cozy. SOLD.

1. 80s PEPSI COLA Raglan Pullover: Fewer things are cooler than vintage and this bright blue Pepsi-Cola sweatshirt is very cool.
2. Vintage 1990s Reebok Sweatshirt: I love that this one has a small logo so if you don’t like to dress “loud” this one is a great option.
3. Vintage 90s Adidas Equipments Big Logo Sweatshirt: If you want sporty then an Addidas sweatshirt is a perfect fit for you! I really love the blue accent on the sides.

Well, that’s it from me today. Again hope this inspired you to try something new while still staying warm and comfortable:)

Love you, meant it.

Opening Image Credits: From: My Favorite 2021 Fashion Styling Hacks/Trends – A Step By Step How To Make Your Comfortable Clothes Look Like You Still Care

The post 18 Cool Sweatshirts And 6 Fun Ways To Style Them For Maximum Comfort appeared first on Emily Henderson.

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