How to Dress up a Sweatshirt

Co-authored by Cassandra Sethi

Last Updated: December 1, 2023

If you want to achieve a laid-back, cute style, you can easily dress up your favorite sweatshirt. Pair your sweatshirt with other tops such as tees and blazers, and add bottoms like skinny jeans or tights and a skirt. You can also add other items like sneakers, heels, statement necklace, and sunglasses to embellish your ensemble. With the right garments, you can style your sweatshirt for business-casual settings and casual, stylish outfits.

Part 1

Part 1 of 3:

Layering Tops

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To choose a versatile sweatshirt that you can wear to casual office environments or around town, go with 1 that is fitted in shape and free of logos or designs. A plain, non-athletic sweatshirt works great.
2
Wear a tee underneath and a blazer on top for a business-casual look. First, put on a white T-shirt that is longer than your sweatshirt. Then, put on your sweatshirt. Finally, wear a blazer on top of your sweatshirt for a polished addition.^{[1]
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- This is a great idea if you need a winter outfit to wear to the office on casual Friday.
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Put on a button-down underneath for a touch of professionalism. Put on a button-down with a collar first, and let the collar sit above the sweatshirt. In addition, you can allow the bottom of the shirt to poke out from underneath. You can also cuff the sleeves of the button-down around the sleeves of the sweatshirt. This adds color and texture to your outfit.
- Try wearing a multi-colored, plaid button-down with a plain gray sweatshirt. Wear this to brunch with friends or for a casual meeting.
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Throw on a structured, sleeveless dress on top for an edgy look. This looks best with fitted sweatshirts without a hood. Choose a sleeveless, colored dress with a structured shape, and wear it on top of your plain sweatshirt for an office-to-party outfit.
- You can select a cream-colored sweatshirt to wear with a burgundy dress.

Part 2

Part 2 of 3:

Pairing Bottoms

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1
Wear your favorite pair of jeans with your sweatshirt for a casual look. If you want to wear your sweatshirt around town or for a night out, select a pair of jeans that fit great. You can go with a skinny jean for a modern look, or choose a bootcut pair for a traditional style. This looks great for running errands, hanging out with friends, or going to the movies.^{[2]
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- You can choose a navy hoodie with white skinny jeans for a chic look.
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Choose a pair of leggings if you want a comfy outfit. To pull off the laid-back look, select a pair of structured leggings in cotton or leather material. Wear leggings with your sweatshirt if you are grabbing coffee with your friend or going grocery shopping.^{[3]
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- Combine a pair of black leather leggings with a fitted black sweatshirt for a monochromatic look.
3
Select a skirt and tights with your sweatshirt for a more polished look. If you want to wear your sweatshirt in a stylish, feminine way, try pairing it with a mini-skirt or knee-length skirt with a pair of tights underneath. This is a great way to make your outfit a bit dressier, so you can wear your sweatshirt to work, on a date, or for a night out.^{[4]
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- For instance, select a solid-colored sweatshirt to wear with a black, faux leather skirt and black opaque tights. Put on a pair of heels, and wear this to the club on a fall or winter night!
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Pair your sweatshirt with trousers for a business-casual look. If you want to make your sweatshirt look professional, wear it with a pair of tailored trousers. This makes your outfit look pulled together and presentable, rather than laid-back and casual.
- Try pairing a plain tan sweatshirt with a pair of brown trousers and a neutral-colored loafer.
- You can also try layering other garments underneath, such as a collared, button-down shirt. This ties together your outfit, so you look neat and professional.

Part 3

Part 3 of 3:

Adding Accessories

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1
Throw on a pair of cool, funky sneakers for a personalized statement. Select a colorful or patterned pair of shoes such as Converse, Vans, or Doc Martens. You can wear high-top or low-top styles, based on personal preference. This is a great way to add a touch of urban flair to your laid-back look.^{[5]
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- Combine a red sweatshirt and light blue wash of denim jeans. Then, wear a checkered shoe for a pop of color.
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Add a pair of heels to your ensemble for a dressy touch. If you want to elevate your look, put on a pair of pumps or wedges. This is a great idea if you are wearing a dress or trousers, for instance. Select a neutral-colored shoe for a subtle addition, or choose a brightly-colored pair for a pop of color.^{[6]
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- You can wear a pair of black heels with black trousers and a grey sweatshirt.
- You can also wear a pair of purple pumps with light-washed skinny jeans and a colored sweatshirt.
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Use a stylish clutch, purse, or backpack to carry your items. A great way to dress up your sweatshirt is with a stylish bag. Grab a clutch if you are going out to dinner or the club, use a purse if you have a lot of items, or go for a backpack for a masculine style. Either way, using an attractive bag adds a personalized touch to your look.^{[7]
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- For example, go with a briefcase-style purse if you are wearing your sweatshirt to the office.
4
Add a large, statement necklace if you want a pop of color. If you want to embellish your outfit, try adding a colorful statement necklace. Select 1 with beads, rhinestones, or semi-precious stones for a stylish addition. Let the necklace sit on the outside of your sweatshirt so you can show it off!
- Try wearing a baby blue and royal blue, floral statement necklace with a navy sweatshirt and jeans.
- Add rings, bracelets, and earrings.^{[8]
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  Expert Source
  
  Cassandra Sethi
  Personal Stylist & Image Consultant
  
  Expert Interview. 31 August 2021.}
- Don't forget makeup is an accessory! Wear a bolder lip color to look put-together.^{[9]
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  Expert Source
  
  Cassandra Sethi
  Personal Stylist & Image Consultant
  
  Expert Interview. 31 August 2021.}
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Wear a pair of trendy shades with your outfit to add a touch of glam. Throw on an oversized or aviator-style sunglasses to finish your look. This small accessory can make your outfit look more pulled together. Choose a brightly-colored pair for a pop of color, or select a neutral pair to wear with many outfits.
- Try wearing a pair of patterned leggings with a plain sweatshirt, then put on a bright red pair of sunglasses.

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How do you make a sweatshirt look cute?

Cassandra Sethi
Personal Stylist & Image Consultant
Cassandra Sethi is a Personal Stylist, Image Consultant, and the Founder of Next Level Wardrobe, a luxury personal styling service for busy professionals. With over 20 years of fashion industry experience, Cassandra helps people transform their confidence by creating a work wardrobe they love to wear. Cassandra holds a BA in Fashion Merchandising from California State University, Long Beach, and a Postgraduate Certificate in Fashion Buying and Merchandising from the London College of Fashion. She created Soulcycle's retail business and was the Senior Buyer for 90+ Equinox gyms. Cassandra has been featured on New York’s PIX11 in an interview about how to achieve great work-from-home style as well as in Men's Health, Business of Fashion, and NYMag.

Cassandra Sethi

Personal Stylist & Image Consultant

Expert Answer

Well, accessories are the way to go, really. This is a low investment category that is fun to play with. Experiment with different earrings, bracelets and rings!

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Before you wear your sweatshirt to the office, make sure it fits in your dress code policy. Some offices may not allow you to wear this while at work, while others will find this totally fine.

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