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How to Dress Up a Sweatshirt: 5 Easy Steps to Look Chic

How to dress up a sweatshirt in 5 easy steps: add a blazer, wear it with a denim mini and leather jacket, a printed midi skirt, wide jeans or a matching set.

By How Do You Fashion · Updated · 3 min read

How to Dress Up a Sweatshirt: 5 Easy Steps to Look Chic

A sweatshirt is the comfiest top you own, but it does not have to look like gym wear. With the right layers and bottoms, it can look cool and put together for coffee, shopping and even a casual dinner.

Below are 5 easy ways to dress up a sweatshirt, each with a real outfit and labels on the photo so you can see exactly what to add.

Quick answer: Throw a blazer or leather jacket over your sweatshirt, swap leggings for a skirt or wide jeans, and finish with clean sneakers, tall boots or loafers.

Step 1: Add a Blazer on Top

A woman sitting on a bench in a green graphic sweatshirt, a grey blazer, a cap and sneakers1Blazer on top2Graphic sweatshirt3Clean sneakers
Photo: sofiamcoelho on Instagram

A blazer is the fastest way to dress up a sweatshirt. It adds sharp shoulders and makes a sporty top look smart casual.

Quick tip: Choose an oversized blazer so the sweatshirt fits under it.

Step 2: Try a Denim Mini and Tall Boots

A woman in a blue graphic sweatshirt, a black leather jacket, a denim mini skirt and tall black boots1Sweatshirt2Leather jacket3Denim mini4Tall boots
Photo: amaka.hamelijnck on Instagram

A sweatshirt with a denim mini skirt and tall boots looks cool and girly. A leather jacket on top adds edge.

Quick tip: Add black tights when it is cold.

Step 3: Pair It With a Printed Midi Skirt

A woman in a grey sweatshirt, a black leather jacket, a printed midi skirt and heeled boots1Grey sweatshirt2Leather jacket3Printed midi4Heeled boots
Photo: hannamw on Instagram

A grey sweatshirt with a printed midi skirt is a fashion editor favorite. The mix of casual and pretty feels fresh.

Quick tip: Tuck the front of the sweatshirt into the skirt for shape.

Step 4: Wear It With Wide Jeans

A woman in a navy half zip sweatshirt and light wide jeans holding a yellow bag1Half zip top2Light jeans3Fun bag
Photo: mv.tiangue on Instagram

A half zip sweatshirt with wide jeans is relaxed but polished. A fun bag adds personality.

Quick tip: Half zips look a little dressier than hoodies.

Step 5: Go for a Matching Set

A woman in a peach sweatshirt and matching joggers on a city street1Matching set2Joggers
Photo: inthing_ on Instagram

A matching sweatshirt set in a soft color looks intentional and pulled together. Add sunglasses and a nice bag to finish.

Quick tip: Pick a set in a thick, soft fabric for the best look.

Mistakes to Avoid When Dressing Up a Sweatshirt

  • Wearing a faded or pilled sweatshirt
  • Pairing it with gym leggings when you want to look dressed up
  • Choosing one so long it hides your whole shape
  • Wearing running shoes with dressy pieces
  • Skipping a jacket or blazer layer

FAQs

How do you make a sweatshirt look dressy?

Add a blazer or leather jacket, wear it with a skirt or wide jeans and finish with boots, loafers or clean sneakers.

Can you wear a sweatshirt with a skirt?

Yes. Denim minis and printed midi skirts look great with sweatshirts.

What shoes go with a sweatshirt outfit?

Clean sneakers, tall boots, heeled boots and loafers.

Is a half zip dressier than a hoodie?

Yes. A half zip or crewneck looks more polished than a hoodie.

Comfy Can Be Chic

Dressing up a sweatshirt is all about one smart layer and the right bottoms. Try a blazer or a skirt and you will wear your sweatshirts way more often.

More ideas: how to dress up sweatpants, how to dress up leggings and comfy winter outfits.

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