The Trendy Y2K Brand Our Editors Reach For Every Season

Woman wears black coat, red Gucci horsebit bag and red Steve Madden Cherish pumps.

(Image credit: @anna__laplaca)

One thing about Who What Wear editors is that we can't resist a good shoe. Whether it's a splurge-worthy designer pair of heels or a simple, no-frills ballet flat, our editors try and buy hundreds of pairs of shoes a year. One brand we reach for time and again? Steve Madden. While the fashion-forward brand has doled out an assortment of handbags, accessories, and ready-to-wear pieces over the years since taking off in the '90s, Steve Madden shoes remain at the forefront of the label's DNA, with the brand churning out dozens of chic, luxe-looking pairs each season. Sign us up.

I thought it would be fun to do a roundup of editor-approved picks from the brand. Below, I handpicked some of my favorites, including knee-high platform boots (a favorite of Gen Z), ankle boots, block-heel sandals, and even one very bold pair of mesh flats I've incorporated into my own closet. Happy shopping!

Woman wearing red Cherish Steve Madden heels with black jeans and brown coat.

(Image credit: @katcollings)

Woman wears rhinestone mesh Steve Madden flats with white slip skirt.

(Image credit: @balencianas)

Man wearing black jeans, black work jacket, and white-and-black Steve Madden loafers.

(Image credit: @bobbyschuessler)
Assistant Shopping Editor
Ana Escalante is an award-winning journalist and Gen Z editor whose work ranges from dissecting size inclusivity at fashion week to discussing how American Girl Doll meme accounts are the the answer to society's collective spiral. She's covered it all: Queen Elizabeth II's corgis, Roe v. Wade frontline protests, and the emergence of jorts (or jean shorts for the uninitated). At Who What Wear, Ana is responsible for delivering smart, insightful, personality-driven shopping guides and trend features for a digital-first generation.Before joining Who What Wear, Ana was Glamour magazine's editorial assistant, where she focused on daily news and special packages, including leading the brand's 2022 Met Gala coverage. For more than half a decade, she has covered style, beauty, and digital culture for publications such as Paper magazine, Harper's Bazaar, Vogue Japan, and Allure, among others. Ana has been called a rising star in media by publications such as Nylon and Teen Vogue. (Her mother, meanwhile, calls her "the coolest person" she knows.)