5 Midi Skirt and-Boot Pairings I'd 100% Wear
People tell me winter is just around the corner, but I have yet to see evidence of this myself. Here in West Hollywood, in fact, we're walking around in jeans, T-shirts—maybe a light denim jacket when those Santa Ana winds really start blowing. Meanwhile, my East Coast colleagues have already pulled out the big guns, i.e., puffer jackets, peacoats, and other items I don’t own. So, you can imagine I was a bit surprised to take note of one particular winter-ready outfit formula on Instagram that feels useful for us all. I’m talking, of course, about pairing a good midi skirt with a good pair of boots. (New Yorkers, y’all might want to add tights.) Keep reading to see five pairings I’ll 100% be wearing this season.
Style Notes: Don't be afraid to double down on It prints. Exhibit A? María Bernad's mock-croc look in an earthy color scheme.
Style Notes: Worried about chilly temperatures? Pair a midi skirt with knee-high boots to bridge the gap.
Style Notes: Pair a bolder skirt with a more subdued pair of Chelsea boots. (Bonus points for a sleek patent finish.)
Style Notes: We love the juxtaposition of futuristic low-rise boots with a simpler retro-vibe wrap skirt.
Style Notes: Last but not least, we love the way Josephine Bredsted toughened up a sweet floral skirt with menswear-inspired hiking boots.
Next up, see four more outfit ideas I got on Instagram.
-
Hailee Steinfeld's Soft, Ethereal Glam Is My Entire Bridal Mood Board, so I Asked for Her Go-To Product Recs
From a peachy-girl blush to an "instant glow" serum.
-
I Spent My Downtime This Weekend Shopping Chic New Fall Arrivals—33 Standouts From J.Crew, Abercrombie, and Old Navy
Immediately adding to cart.
-
6 Fashion Editors, 36 Summer Buys—Inside Our Summer 2025 Mood Boards
Everything inspiring our wardrobes this season.
-
The Pretty Dress Trend L.A. It Girls Are Bringing Into Fall (and the "Basic" Style They Already Forgot About)
It's finally time to part ways with boring linen dresses.
-
Experienced Shoppers Are Styling Cowboy Boots With This Specific Denim Trend to Make Them Look Less Costumey
Take a page out of Kendall Jenner's style book.
-
I'm Manifesting a Fashionable Fall in NYC With These 36Replica Store Anniversary Sale Finds
Frye, AllSaints, Vince, Coach, and more.
-
If I Saw You in Any of These 15 Summer-to-Fall Transitional Outfits, I'd Think You Hired a Stylist
Nice taste.
-
Put Down the Black and White Pants—This Is the Richer Color You Didn't Know You Needed
Elegant and on-trend.
-
I Thought Wearing These Shoes With Shorts Was Cringey—Turns Out the Combo Is Peak 2025
Apologies are in order.
-
10 Outfits Europe's Chicest Dressers Are Wearing When They're *Not* on Vacation
Staying local is cool.