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)
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Ana Escalante
Associate Features Editor

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.