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.
-
5 Fall and Winter Trends I'm Plagiarizing From Lucy Williams, Aimee Song, and Camille CharrièreWhich one is more your vibe?
-
If Chic Jeans-and-Boots Outfits Are the Goal, Don't Miss These Standout Picks From Zara, Madewell, andReplica StoreBring on a stylish fall-and-winter closet.
-
No More Neutrals! 4 Fun Outfit Ideas for When You're Sick of BeigeInspo ahead.
-
My Honest Take on the Winter It Boots Every Fashion Person Is Talking AboutFrom Khaite to Free People.
-
Of All Her Outfits, *This* Hailey Bieber Look Is Stuck in My BrainAnd I will be re-creating it.
-
Just so You Know, Zara Already Has All the Best Shoes for Winter 2025Shop before they sell out.
-
Cool Sneakers, Flats, and Boots Are the Vibe—These 36 Styles Are Heavily Discounted for Cyber MondayEverything from Khaite to Ref to Adidas is at least 25% off.
-
If You're Going to Wear a Dress With Ankle Boots, This Is the Trend That Looks the Least DatedPSA via Suki Waterhouse.

