3 Ways to Wear a Dress Shirt Without Dressing Up

Don’t believe the hype: a “dress shirt” isn’t just for formal attire. So if you think this key closet staple is too stuffy for your style, think again. See our expert gamechangers to dress down your dress shirt and be the most clever-looking guy in the room.

The dress shirt’s been held down for far too long. Keep reading for 3 unconventional ways to wear the coolest piece you already own.

Stitch Fix Men's outfit laydown featuring an orange vest over a blue long sleeve button-down shirt, olive green jeans and cream lace-up sneakers.

How to Wear a Dress Shirt and Chinos

Extend the range of a spread-collar dress shirt with this down-for-whatever look. Just start with olive chinos and layer with a fleece vest. Style your dress shirt untucked for an effortless casual look.

Stylist pro tip: Choose rich colors for a bold, crisp pairing.


Stitch Fix Men's outfit laydown featuring white and grey striped henley shirt, sage green long sleeve button-down shirt and grey jeans next to white sneakers on a white block.

How to Wear a Dress Shirt and Jeans

Up the edge on your basic dress shirt with our Stylist’s modern take. Just pair tailored grey jeans, your go-with-anything workhorse, for a sleek, simple look that has massive appeal. Then add a neutral striped henley as your laid-back essential that balances the outfit. Keep the city vibes on-point with leather sneakers.

Stylist pro tip: Old style rules are out. White can totally be worn past Labor Day.

Stitch Fix Men’s shacket outfit with blue and white plaid shacket, blue hooded sweatshirt, gray jogger pants, gray sneakers.

How to Wear a Dress Shirt and Joggers

Yep, a dress shirt can feel leisurely right at home with this stress-free pairing. Take your button-down dress shirt into the comfort zone by wearing with jogger pants. Aim for gray—a color that seamlessly elevates any look—in a light fabric. Throw in your softest lightweight hoodie and favorite shell-tops.

Stylist Tip: The cut of your joggers can easily nail or kill your outfit. Make sure your perfect pair is tapered and trim.

Have we convinced you to rock a dress shirt any day of the week? We thought so. Take your style quiz and ask your style expert for dress shirts when you schedule a Fix. You’ll be sporting a button-down and joggers on football Sunday in no time. Shipping and returns are always free.

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