Uniform

In college (and the years after, come to think of it), any time a young man would find out that I had attended an all-girls Catholic high school, I’d get the question (typically accompanied with a knowing/randy smirk): “Did you wear one of those uniforms?” I’d watch them squint their eyes, no doubt conjuring up some fanciful vision of pretty young things involved in pillow fights, girly shenanigans, interdicted cigarette smoking, sneaking behind a nun’s back, etc., all while wearing a short plaid skirt and looking beautiful and bright.

Um, the truth could not be further from this vision.

At my school, the girls rolled up with frayed skirts (by the time my youngest sister inherited my kilt, it was basically a threadbare scrap of vaguely plaid wool that could have served as a belt) worn over boxers or sweatpants (extra points if the sweatpants were from a good college, which suggested you had college-aged contacts and/or an older brother who might have attractive friends), a bleached and stained polo shirt (the rattier, the better — this usually indicated you’d inherited your polo from an older sister or cousin, which was obviously cool; the goal was to make our standard-issue banana yellow polos as close to white as we could), ratty-ass shoes, and a general, likely feigned, air of nonchalance. Hair was unkempt and messy — the rat’s nest was the look we were going after. Makeup was considered gauche. Around my junior year, an independent survey studied a range of similar all-girls Catholic schools and scored us the lowest on “hygiene.” I recall that we wore this as a badge of honor. The rattiness was so bad that one of my friends showed up at a high school dance and didn’t recognize a single person for the first few minutes…and then slowly rubbed her eyes in disbelief as she began to identify her classmates.

Funny, then, that though I associate my kilt with a period during which I looked my grungiest, I’m loving plaid for this fall. How amazing is this super-affordable plaid bomber ($35 — LOVE.) with classic gold earrings (David Yurman, $1,800), skinnies, and some of those Stubbs + Wootton flats ($600)?

Add a pop-of-red mini ($195) to finish:

Or, how about this fab topper (Stella McCartney, $750) —

— over a great white knit sweater ($295) and roughed up jeans ($168), topped off with these incredible flats ($98, plus extra 40% off today!):

I love this look paired with this Sophie Hulme tote ($894):

For a holiday affair, how about this sweet skirt (Alice + Olivia, $330) with a simple black Tippi sweater ($80) and a show-stopping necklace (Erdem, $1,205):

Black bow-toed Choos are the perfect accent ($850), especially alongside this adorable clutch (Zac Posen, $275):

For a slightly edgier look, check out this scalloped leather peplum top (hitting all the trends at once, eh? — $395) with this buffalo plaid skirt (Alice + Olivia, $242 — or get the look for less with this Zara skirt), tights, and suede booties ($425):

I know I feature this bag a lot, but I love it in the black with this look (Clare Vivier, $500):