How to Style a Sweatshirt (and Not Look Frumpy)

*This page contains affiliate links, which do not affect price but allow me to share a small commission. As an Amazon Associate, I earn from qualifying purchases.*

Remember how, at one time, sweatshirts were considered frumpy? Boy, how that’s changed! With the rise of athleisure wear and the shift to more casual lifestyles, sweatshirts have evolved. They’re softer, more fitted, and so much cuter than ever before.

Today, I’m sharing some of my favorites, and ways to wear sweatshirts that feel comfy, stylish, and totally age-appropriate. These are all Amazon finds that are affordable and flattering,  proof that you can look pulled together and still be comfortable.

Leopard print sweatshirt | Black Itty Bitty Jeans | Suede Boots | Woven Faux Leather Bag

1. Animal Print Sweatshirt

Gone is that ugly varsity number from your college days or some heavy, oversized monstrosity with a hood. The new sweatshirts are lightweight, fitted, and chic.

For example, this cute Amazon sweatshirt is a fun mix of two very different looks – sporty and glamorous. You’ve got the coziness of a sweatshirt combined with an edgy animal print, making for a modern look.

I like to style animal print with black jeans. It gives this casual outfit a sleek, dressier look than a pair of regular blue jeans, and that inky black also makes the leopard spots pop!

striped sweatshirt  | Itty Bitty Bootcut Jeans | Straw tote | Silver sneaker

2. Classic Striped Sweatshirt

My favorite type of sweatshirt is one with stripes because I adore a cute and sporty nautical look in summer. This navy and white striped crewneck sweatshirt is a classic that pairs well with jeans, pants, and shorts.

I also love to tie a striped sweatshirt around my neck and wear it with a shirtdress or a plain tee. It adds depth and color to your outfit — and when it gets chilly, just pull it on. I always travel in a sweatshirt like this in summer!

Here, I’ve styled it with Itty Bitty bootcut jeans, silver sneakers (a fun change from white), and a summery straw tote. It’s casual, fresh, and ready for anything — I look like I’m about to step onto someone’s boat!

fleece quarter-zip sweatshirt |  Not Your Daughter’s Jeans | white sneakers

3. Zippered Sweatshirt with a Collar

This is another sweatshirt style I love because it has a great face-framing collar, pockets, and a sporty zip neckline. Sometimes all you need is something bright and cheerful — like this one paired with crisp, white, cropped jeans. It’s a look that feels summery, fresh, and put-together.

You’ll notice that this sweatshirt, like the others I’m sharing, is quite fitted. They aren’t tight, but they follow your shape much more closely than a traditional sweatshirt. Of course, you could easily go up a size if you prefer a more relaxed, oversized vibe.

short puff sleeve striped sweatshirt | Itty Bitty Boot jeans | silver sneakers

4. Short Puff-Sleeve Sweatshirt

This cute little number might be my favorite sweatshirt in a long time. It has short puffed sleeves — and when I saw it on Amazon, I thought, “What a great idea!” I’m always eager to roll up my sleeves for a sporty look, so why not try a sweatshirt that does it for me?

The slight puff at the shoulder makes it feel feminine and a little fashion-forward, without being over the top. It’s such an easy way to add personality to a casual outfit. In keeping with the nautical vibe of the sweatshirt, I’ve styled this with bootcut jeans. The slight flare gives a sailor vibe.

terry fleece sweatshirt | woven tote | white jeans | sandals

5. Aqua Crewneck Sweatshirt

If this sweatshirt looks familiar, you’re right! It’s the same one as the leopard and striped versions. I love it so much I’ve bought it three times. All the sweatshirts I’m sharing today are from Amazon Essentials — good quality for the price, and always classic with a slight modern twist.

I fell in love with this aqua color the minute I saw it. It’s even prettier in person, and when paired with white raw-edge jean,  you definitely get that vacation vibe — white sand, turquoise water, and a soft breeze. It’s such a breezy, calming look.

All of these sweatshirts are lightweight, soft, warm, and slightly fitted. I’m wearing a size small, and they fit true to size.

striped pullover hoodie | Itty Bitty Boot Jeans | Silver sneakers

6. Striped Hoodie

Okay, there I go again with those stripes! I love them in summer, but I also picked up this one because it has a hood. I don’t usually wear it up, but it adds a casual, sporty vibe that’s just cute. This hoodie comes in other colors if you’re ready for a stripe break!

It’s a practical and relaxed style to wear, whether you’re on a boat or in the backyard. And, it’s perfect for travel — comfy, lightweight, and easy to layer.

Summer Blue Sweatshirt |cropped chinos | Silver sneaker

7. Summer Blue Sweatshirt

When the color is this pretty, you can skip the extras. This gorgeous French blue sweatshirt is one of my favorites — it really brightens my face. I styled it with slim, cropped chinos for an easy, summer look that’s casual yet pulled together. The silver sneakers give it a sporty fashion forward look.

More Sweatshirts

So that’s it. There are many other types of sweatshirts available at various price points throughout the summer. I really like this floral sweatshirt I got last season, and it’s always fun to wear a graphic sweatshirt with a playful message. There’s a sweatshirt for everyone these days!

How to Choose the Right Sweatshirt for You

Here are a few simple style tips to help you look modern and confident in a sweatshirt:

• Pick a polished print or color. Stick to stripes, solids, or animal prints in sophisticated shades.
• Look for a streamlined fit. Avoid bulky shapes and choose one that follows your curves without clinging.
• Keep embellishments minimal. A little detail is great — too much adds bulk or looks dated.
• Balance the proportions. Pair a relaxed sweatshirt with fitted bottoms, or vice versa.
• Mind the hemline. If you’re bottom-heavy, avoid tight bands; a looser hemline is more flattering.
• Add accessories. A simple necklace, sporty watch, or statement bag adds instant polish.
• Don’t forget great shoes. Trendy sneakers, ankle booties, or even a wedge sandal can dress things up just enough.

And my favorite finishing touch? Lipstick! It’s amazing how a little color brightens your whole look and keeps a casual outfit from feeling blah.

Final Thoughts

The newest sweatshirts strike the perfect balance between comfort and style. A modern sweatshirt that fits well and flatters your figure can make you feel cozy, confident, and totally fabulous — proof that casual doesn’t have to mean frumpy.

Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

Learn More About Deborah Explore Her Latest Posts