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.

Another season, another It skirt.

A luxe take on cat-eye sunglasses.

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

A simple silhouette to ground the look with.

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

We've never seen a leopard-print skirt we didn't need immediately.

We love a little shine in our block-heel boots.

Add some cheer to your winter wardrobe.



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

You'll actually wear this everywhere.

Style Notes: Last but not least, we love the way Josephine Bredsted toughened up a sweet floral skirt with menswear-inspired hiking boots.

These go with everything (promise).

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