Whether you decide on a flippy mini or slim pencil style, plaid skirts skew way too prep school for a Cobain vibe. To avoid looking too prim and proper, though, mix it with something slightly tomboy, like an leather bomber or boxy cable knit.
The perfect balance of cereal and cartoons casual and fancy enough for a reservation-only restaurant, this look is even office-appropriate with the right blazer. (For an after-hours party, though, you should swap it for a moto jacket.)
Mint, lavender and dusty rose's inherently feminine feel makes most every plaid piece feel a little retro. But so long as you mix in a few modern pieces—an ugly-cool shoe here, a bucket bag there—the look won't be dated.
Stroke of Luxe Dress in Plaid, $51.99, modcloth.com; Plaid cotton and silk-blend blazer, $324.97, Suno, theoutnet.com; Leather Sleeve Plaid Jacket, $790, Thakoon Addition, shopbop.com