Maybe it’s the eternal kid in me who associates September with “back-to-school” time, but it happens without fail. Whether you were subjected to a uniform of pleated skirts or not, fall and plaid will always go hand in hand. But instead of going all Catholic schoolgirl, trade in the typical prep-school vibe for a shoe that gives plaid a whole new connotation: Edgy! Strong! Sexy! These picks run the gamut, but all steer clear of conservative.

1. Christian Louboutin Intern Spiked Cap-Toe Plaid Loafer: The logo crest is pure camp on this slipper. How can you tell? A spiked-out cap-toe, of course.
At Bergdorf Goodman for $895.

2. McQ Alexander McQueen Patent Plaid Creepers: Take your plaid with a side of punk, and wear this dark tartan with a pair of slinky, cropped skinnies.
On Shopbop for $530.

3. Marni Plaid Flannel-Covered Leather Loafers: The most traditional of the bunch, these will be best worn with an itty-bitty miniskirt or a short leather sheath-dress.
On Net-a-Porter for $610.

4. Marni Calf and Tartan Lace-Up Shoes: Marni shoes they can also do plaid with a sense of humor. Grunge-inspired oxfords ought to be styled with a light degree of dishevelment.
On Luisa via Roma for $630.

5. Christian Loboutin Jenny 150 Tartan Slingbacks: Plaid rarely gets vamped up like this. This sexy slingback is made for lingering stares (and not for long walks).
On Net-a-Porter for $945.