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1. Wear a tartan skirt.
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.
2. Mix in lipstick and heels.
A page straight out of Jenna Lyons' playbook (AKA, the bible): the secret to saving baggy flannels from looking sloppy is ladylike accessories. Gold star if you wear tortoiseshell glasses, too!
3. Layer plaids.
It's playful-preppy in the best kind of way—and 100 percent the opposite of what a Seattle rocker would wear.
4. Style your flannels with wide leg trousers.
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.)
5. Buy pastel plaid.
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.