Unlike the strict interdiction against white pants and shoes (which should, under penalty of death, never be seen upon your person after Labor Day), the rules about wearing shorts beyond the unofficial end of summer are nebulous at best. And where some people are happy to pack away their cutoffs and culottes come September, I prefer to wear mine until someone pries them off my cold, dead body with a crowbar! ...Or at least until it's too chilly to be wandering around with exposed thighs.
Fortunately, it's now possible to wear shorts well into the fall, and to do it without violating even a single old-school rule of fashion (including the one about open-toed shoes.) Because ankle boots! Yay! Which suddenly became ubiquitous a couple years ago, and seem to be here to stay, thus giving us a way to expose our lovely, still-bronzed-from-late-summer legs during apple-picking and pumpkin-eating season while still keeping our toes toasty. Need an example? Check out this girl; she's got the look down, even if her vest violates every known rule about when and with what to wear fur, not to mention all the ones of good taste as well. And for Exhibit B...
It's me! In some frayed teal cutoffs, a pair of pirate-style wedges, a chiffon peasant shirt, and a summer scarf.
The secret to stretching your short-age into back-to-school season? Layers! Lots of 'em. Pick a bunch of lightweight pieces over a single heavy one: a flimsy tee plus a fluttery top plus a drapey cardigan plus a linen scarf is very bohemian-chic, and will keep the chill away without making your bare legs look like a weird mistake. Whereas shorts and a bulky wool sweater will make you look like a crazy person. Okay? Let's all try it!
Head to toe: top, TJ Maxx; shorts, Old Navy; boots, DSW (Madden Girl); scarf, LinenMe; earrings, vintage.