If there's one thing Parisians and the Milanese actually agree on (besides espresso and expertly executed haircuts), it's the unmatched chicness of a great skirt-and-boot combo. As a fashion editor, my work involves finding the best street style during fashion month, and frankly, if there's one style formula I saw everywhere, it was a sleek slip skirt paired with the perfect boots. Whether it was ankle boots with an oversize blazer or knee-high boots with a slinky satin blouse, the streets were a master class in looking like you didn't try… but definitely did.
Naturally, I'm now on a mission to re-create the magic without hopping on a flight to France or Italy. I've rounded up the best outfits to shop now, inspired by the cool girls effortlessly strutting through the arrondissements and cobblestone streets of Milan. Below, shop the best slip skirt and boots outfit ideas.
How to style: Camel slip skirt, oversize blazer, and black ankle boots.
How to style: Ivory slip skirt, '60s ruffled top, and brown knee-high boots.
How to style: Peony slip skirt, ribbed tank, and red ankle boots.
How to style: White slip skirt, V-neck sweater, and slouchy black boots.
How to style: Black slip skirt, textured knit sweater, and suede knee-high boots.
How to style: White slip skirt, gray cardigan, and black knee-high boots.
How to style: Black slip skirt, silk tie-front blouse, and heeled pointed-toe boots.
How to style: Leopard-print slip skirt, graphic tee, and combat boots.
How to style: Printed slip skirt, leather jacket, and black chunky boots.
-
If You Want to Look Chic and Rich This Winter, Make Sure You Own This Non-Denim Pant TrendSee what we’re talking about inside.
-
The 2025 Way to Wear Sneakers This WinterOutfit inspiration inside.
-
5 Non-Dated Ways People in Paris, NYC, and L.A. Are Styling Leather Pants Right NowNow all I want to wear are leather pants.
-
Sorry, Crewneck Tees—in 2026, Everyone With Taste Will Be Layering Sweaters Like ThisThe recipe for a perfect winter outfit.
-
You Have About 3 Weeks Left to Wear This Trending Outfit Combo Before Winter Dressing Fully Kicks InHere's the inspiration.
-
The "Weird" But Forward Way Fashion People Are Styling Their Sweaters for Fall 2025You'll either love or loathe it.
-
This Chic Outfit Is Perfect for Paris, But I'm Going to Wear It In the Midwest and NYCThis simple outfit will make you look chic anywhere.
-
If You're Going to Keep Wearing Floral Dresses in the Winter, This Jacket and These Boots Are Absolutely CrucialIt's the only practical (and chic) way.
