How to wear skirts
The best ones out, the best shoes to wear with them, and how to style it all
Welcome to Concorde — Blackbird Spyplane’s “women’s vertical,” except it’s for everyone who is cool. Every edition is archived here.
Blackbird Spyplane — it isn’t just a sletter… it’s a temple of enlightenment.
You know that if you’ve seen our guides on, e.g., How to Wear Colors Well… on How to Layer Dopely… on How to Wear Scarves… on PANTS.
The other day I (Erin) got a question from a SpyFriend (also named Erin) who found herself vexed by skirts:
I need a Concorde tutorial on how to wear skirts. Currently, I only own one and I’ve been drawn to them lately but they feel harder to style somehow. Advice for a fellow unisex-leaning femme?
I get it… Wearing skirts comes with some confounding variables. Time was, trousers on women were a no-go — skirts and dresses were the only “acceptable” garments — but during the 20th century, women insisted on the Right to Pants, they quickly became a second skin, and these days wearing a skirt can feel a bit like speaking a second language. You might associate them with “trying,” with dressing up, or with a degree of girliness you’re wary of… There’s the question of volume, all that fabric swirling around your legs beholden to its own unpredictable physics… Where exactly should a skirt should land on the leg? How do you rock them when the temperatures drop? And once you start to approach an answer to all that, you’re ready for the calculus problem of what shoes and tops to wear with them!
But if you ask me, skirts can be a way easier proposition than pants, and they come with their own distinct sauce-enhancing payoffs.
Which can only mean one thing — it’s time for a Concorde Skirts Report.
Featuring:
The styles & shapes to seek out now, and top-tier examples from small designers,
Ways to build outfits around them,
The kinds of tops I love pairing with them,
The best new & old sneakers, flats and boots to rock with them,
Some slept-on vintage gems priced low — and search terms to help you find them,
And more!
Let’s get to it —
When I’m putting together an outfit centered on a skirt, there are two basic paths I take … They’re both simple, and they give you lots of room to play around.
You can find the full Skirt Report here:
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