The Effortless Skirt-and-Boot Combo I'm Copying From People in Paris and Milan


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.

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
-
I Just Created 5 Expensive-Looking Pre-Fall Outfits FromReplica Store, H&M, and Saks—You're Welcome
Everything you need to kick off September is right here.
-
Fashion People Are Elevating "Boring" White Tanks By Wearing Them With This Elegant Skirt Trend Instead of Jeans
As seen on Zoë Kravitz in Paris.
-
I Was on the Fence About Some Fall Trends, But These 32 New Items Changed My Mind
I've been convinced.
-
In Paris, L.A., and London, Basic White Tees Are Getting Sidelined In Favor of This Cooler Alt
We'll always love you, but it's not your turn right now.
-
Goodbye, Bubble Shorts—Everyone Everywhere Is Wearing This "Dated" Pant Trend Instead
Here's how It girls in New York, London, Copenhagen, and more are styling them in 2025.
-
I'm Not Ready to Say Goodbye to Nantucket Summer Vibes—7 Outfit Ideas to Keep It Alive Through Fall
Nautically chic.
-
Bella Hadid Just Wore the Elegant Heel Trend French Women Are Favoring Over Sandals
It's got that je ne sais quoi.
-
My Friend Wants to Look More Parisian—I Suggested She Wear These 4 Pieces
Easy and chic vibes.
-
Hold the Light-Blue Jeans—People in Paris Know This Denim Trend Is Far Superior for Fall
It's so elegant.
-
I Don't Live in Paris, But These Chic Outfits Make Me Feel Like I Do
Effortlessly cool.