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.
Mock croc is clearly having a moment.
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.
So many colors, so little time.
A simple silhouette to ground the look with.
Cozy and bright.
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.
Simple, yes, but unexpected.
A delicate pair of moto boots.
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.
Extra flair incoming.
These go with everything (promise).
Balloon sleeves for the win.
Next up, see four more outfit ideas I got on Instagram.
-
It's Here: The It Girl Way to Wear a Sweater in 2025Kendall Jenner just solidified it.
-
Everyone in Paris Just Ditched Ankle Boots for This Boot Style That’s Way More ElegantAnd super sexy.
-
*Not* Suede Boots: The Rich-Looking Boot Trend Fashion People Everywhere Are Wearing With Jeans and Skirts for Fall 2025You'll want to add a pair to your rotation.
-
Cooler Than a Trench—This Coat Trend Is Quietly Taking Over for FallRich b*tch vibes.
-
Sorry to the Black Pieces in My Closet—I'm Obsessed With This Equally Chic, Classic Color for FallFashion people from London to Paris agree.
-
*Not* Ankle Boots—The Rich-Looking Shoe Trend That’s Quietly Taking Over for Fall 2025Shop the style inside.
-
Cooler Than Leggings—Everyone With Good Taste Is Wearing This Casual Outfit Combo This FallCount us in.
-
Black Boots Are Fine, But *This* Fall Shoe Color Trend Looks Rich as HellLily James is a fan.
