Button-Up, Stand Out: The Chicest Ways to Style Button Shirts

Buttoned up, open wide, or tucked under a statement jacket, how would style it?

3/9/20252 min read

The button-down shirt is a streetwear essential that has infiltrated sidewalks and street corners with effortless cool over the past few years. The trick? It’s all in the styling. Oversized and untucked, it screams nonchalance. Layered over a graphic tee, it bridges prep with rebellion. Tied at the waist? Suddenly, it’s giving ‘90s supermodel energy.

Spring 2025 is leaning hard into contrast. Think classic crisp white shirts paired with ultra-baggy, low-slung denim, or pinstripes clashing with bold, printed skirts. Bonus points if you throw a leather bomber on top. Sneakers keep it casual, but swap them for loafers, and suddenly, you’re the main character.

Details matter. Rolling the sleeves halfway? Effortless. Leaving the top three buttons undone? Just the right amount of reckless. And if you’re daring, layer two button-downs together—one structured, one soft—for that chaotic-yet-intentional energy street style thrives on.

Button-downs aren’t just shirts; they’re statements. A crisp one reads polished, a wrinkled one says you’ve got better things to do than iron (respect). So, wear it big, wear it loose, and wear it your way—because in 2025, street style isn’t about following rules. It’s about rewriting them.