How to Dress Up a Sweatshirt: 8 Style Tips You Need to Know

For years, the sweatshirt was confined to the gym, the couch, or for running errands in a rush. Definitely not the height of fashion, but it was the ultimate comfort item.

But with the changing style rules, the sweatshirt is now a versatile wardrobe staple that can be worn almost anywhere, from a weekend brunch to a creative office environment. Yes, you can actually use a sweatshirt for a dressed-up look, too. The key lies in learning the high-low balance, pairing its relaxed feel with refined pieces.

Let’s break down how to dress up a sweatshirt in a way that gives it a polished, street-style-worthy look.

Mastering How to Dress Up a Sweatshirt

The sweatshirt is essentially a relaxed piece of clothing, which becomes the biggest challenge when you are trying to infuse it into a chic outfit. Remember one basic rule: if the top half is loose and soft, the bottom half or outerwear must be structured and refined. This balance is what takes your sweatshirt outfits from sloppy to stylish.

A successful dressed-up sweatshirt look starts with choosing the right accompanying pieces and paying attention to detail. Bespoke apparel, including jackets and sweatshirts, tends to work best when you want to elevate a look.

Below are the 8 ways to confidently master your sweatshirt style in a dressy way.

1. Swap Denim for Tailored Trousers

While a sweatshirt and jeans are classic, the combo is undeniably casual. A sweatshirt with dress pants immediately elevates the whole look.

You should consider:

• Wool Trousers: Crisp, black, or charcoal grey wool trousers provide structure and texture that contrast beautifully with a soft fleece top.
• Wide-Leg Pants: A pair of flowy, wide-leg trousers in a rich fabric (like linen or crepe) creates an elegant, elongated silhouette.
• Chinos: For a smart-casual vibe perfect for a creative workplace, you can pair a neat crewneck with slim-fit chinos.

2. The Blazer is Your Best Friend

The layering technique with a structured blazer is great for styling a sweatshirt for any setting that requires a little polish. You have to choose a well-tailored blazer that retains its shape. Oversized blazers work best over slightly fitted sweatshirts, while a tailored, single-button blazer can refine any pullover.

Try a tweed or checked blazer over a solid-colored sweatshirt for visual interest. For sophisticated sweatshirt looks, stick to neutral colors. A black sweatshirt under a grey check blazer, or a white sweatshirt under a tan wool blazer, always looks intentional.

3. Layer a Collared Shirt Underneath

If you ask how to style a sweatshirt to make it feel less like loungewear, go for the preppy, collegiate look, which is definitely all the rage these days. Simply layer a crisp button-down shirt underneath your crewneck or hoodie.

Make sure the shirt is neatly pressed and the collars and cuffs are visible. This frame around the neck and wrists adds a clean, formal touch to the outfit. For extra flair, you can try shirts with a Peter Pan collar for a soft look, or pair a striped button-down with a solid colored school sweatshirt.

4. Use Accessories as Aggressive Opposites

When you want to dress up a sweatshirt, swap out your casual accessories for structured and luxurious pieces. Like add a chunky gold chain or a sleek pendant necklace that hits just above the sweatshirt neckline. Layering delicate necklaces can also be effective.

Ditch the gym bag or canvas tote. Opt for a structured leather tote or a chic mini-bag. If you are tucking your sweatshirt (even just the front), use a high-quality leather belt with a statement buckle. By intentionally investing in the small details, you follow the major sweatshirt trends of styling them as luxury garments.

5. Perfect the Intentional Tuck

An untucked sweatshirt can sometimes look bulky or shapeless. By tucking it in, you create a defined waistline, which instantly makes the outfit look more put-together and thoughtful.

There are three main tucking techniques:

1. The French Tuck (Half-Tuck): Tuck just the very front of the sweatshirt into the waistband of your pants or skirt (works well for slightly oversized fits).
2. The Full Tuck: Tuck the entire hem of a more lightweight or fitted sweatshirt into high-waisted bottoms for a sleek, streamlined look.
3. The “Bra Tuck”: Take the excess fabric at the hem and tuck it up and under your bra band or the waistband of your high-rise bottoms. It will pair perfectly with high-waisted midi skirts.

6. Go Monochromatic for Seamless Polish

A monochromatic outfit with all pieces within the same color family looks intentional, clean, and expensive. You can pair a pale grey sweatshirt with charcoal grey trousers or joggers and white sneakers. Or a black hoodie with black pants and black boots for an instantly sleek and slimming look.

7. Be Mindful Of Your Footwear

The wrong shoes can drag the entire sweatshirt outfit back to the gym. Choose loafers or mules made of leather, as they are quintessentially smart-casual footwear and pair perfectly with tailored trousers.

Sleek leather or suede boots (especially Chelsea or heeled styles) add structure and warmth, making them perfect for cute fall sweatshirt pairings. If you insist on sneakers, opt for sleek, minimalist leather sneakers rather than chunky athletic runners.

8. Focus on High-Quality Fabrics for Sophisticated Sweatshirt Outfits

If you want your outfits with a sweatshirt to feel dressed up, make sure the sweatshirts look high-quality. While traditional cotton fleece is cozy, consider elevated fabrics like French Terry, Cashmere, or Wool blends for a naturally chic appearance. These materials look and feel luxurious, instantly transforming the humble garment into a high-fashion piece.

One more thing to look for is minimal graphics. Look for Chenille patch trends in 2025 to check what could be suitable for your sweatshirt. If you choose a logo or graphic, ensure it is small, embroidered, or sophisticated, not large or overtly casual.

Conclusion

Learning how to dress up a sweatshirt shows how far fashion has come. Because in this day and age, comfort and style no longer need to compete. A well-chosen sweatshirt can look refined when styled with intention. Smart layering, tailored pants, and clean accessories can turn this simple piece into an outfit centerpiece. It’s the balance of ease and structure that defines modern fashion.

At Anything Chenille, we celebrate that balance. Our custom sweatshirts blend comfort with craftsmanship, letting you express your individuality without losing sophistication. Explore our collection and see how dressing up a sweatshirt can become your signature look.