2. Pleated Tennis Skirt & Boxy Graphic Hoodie

Infusing prep-school nostalgia into urban fashion, a crisp white or pastel pleated mini skirt softens the heaviness of an oversized, boxy graphic hoodie. The key to proportion is ensuring the hemline of the skirt peeks just a few inches below the oversized hoodie hem.

Style Tip: Add white ribbed tube socks pulled midway up the calves, paired with retro leather court sneakers and layered silver chains for an authentic 90s streetwear nod.