So That's How to Wear Leggings and Boots

While at first, the thought of pairing leggings and boots sounds like a contradiction (after all, one is for working out, and the other is definitely not), upon further review, we are now on board with the contrasting combo. Admittedly, all it took was seeing the cool yet comfortable pairing on a handful of our favorite celebs, with a common thread among all their looks to boot: an easy third piece. Whether it's with a lightweight flannel à la Kaia Gerber or a sleek black coat inspired by Rosie Huntington-Whiteley, let these ladies show you how to style leggings and boots for any occasion or season.


Rosie Huntington-Whiteley
(Image credit: Marc Piasecki/GC Images)

This all-black look is our ideal dinner outfit.


Gigi Hadid
(Image credit:  MediaPunch/Bauer-Griffin/GC Images)

We can only hope to someday travel as stylishly as a Fendi-clad Gigi Hadid does. For now, we can just steal her combat boot–and-legging combo.


Alessandra Ambrosio
(Image credit: Timur Emek/GC Images)

A bright shearling coat makes an otherwise all-black outfit anything but boring.


Nina Dobrev
(Image credit: SMXRF/Star Max/GC Images)

We love how Nina Dobrev's black boots have a hint of excitement in them. 


Olivia Culpo
(Image credit: Gotham/GC Images)

Culpo's all-black look is a great casual date option to emulate.


Margot Robbie
(Image credit: Backgrid)

We're officially inspired to make a black hat part of our next airport outfit.


Kaia Gerber
(Image credit: Backgrid)

No stranger to the legging-and-boot look, Gerber knows that the key is outerwear.

Shop legging-and-boot combos we love:


Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. It was a less expected route, seeing as she was graduating from business school at USC when this all began, but it has turned out to be the best one for her. Fast-forward to 2024, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was an intern starting out. Currently, she focuses on a weekly mélange of shopping content. As far as her personal style goes, she's largely drawn to classic pieces and neutral basics but will always make an exception for something colorful, printed, or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a good party is dressing up for one. On weekdays, she can usually be found at home eating something delicious for dinner and trying to force her husband to watch Summer House.