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.
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