5 Midi Skirt–and-Boot Pairings I'd 100% Wear


(Image credit: @chloechill)

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.


(Image credit: @mariabernad)

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.


(Image credit: @chloechill)

Style Notes: Worried about chilly temperatures? Pair a midi skirt with knee-high boots to bridge the gap.


(Image credit: @ada_oguntodu)

Style Notes: Pair a bolder skirt with a more subdued pair of Chelsea boots. (Bonus points for a sleek patent finish.)


(Image credit: @mamacaxx)

Style Notes: We love the juxtaposition of futuristic low-rise boots with a simpler retro-vibe wrap skirt.


(Image credit: @josephinebredsted)

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.