The 50 Chicest Shoes to Wear This Fall

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Depressed at the thought that winter is coming? Luckily, we have a few more months before we’re stuck in snow boots and giant parkas, and in those months, there are plenty of fantastic shoes to wear. This fall, the mary jane is back after making appearances on the runway at Michael Kors, Miu Miu, and Prada. If you’re on the hunt for boots, the choices are equally fantastic, whether you prefer a knee-high option or cool ankle styles. And should you want a fun, colorful heel that’ll dress up anything from jeans to a black dress, everyone from Gucci to J.Crew has something made for a party. Click ahead for the best shoe porn of the season.

A Signature Ankle Boot

Don’t default to plain black booties to get you through winter. If there’s no shoe-ruining snow on the ground, why not experiment with fun colors and textures? Asos’s red faux-python pair, Loewe’s striped version, or Maison Margiela’s shiny silver style can turn a pair of jeans and a cozy sweater into a signature look.

The Anti-Ballet Flat

Delicate, round-toe ballerina slippers won’t ever go out of style, but they can feel stale after a few years. To mix it up, try this slinky lace-up alternative. Aquazzura’s version has been around for a few seasons and usually sells out. For a more budget-conscious version, Massimo Dutti’s sleek black version looks far more expensive than it is.

Boots High Enough to Skip Tights

There comes a fall day when it finally becomes too cold to go bare-legged. You can delay the inevitable with a boot that hits your knee or higher. Zara’s version features a sexy lace detail in the back, while Saint Laurent’s is sleek and elegant. And for those who want a roomy calf, Stuart Weitzman’s style stretches and Madewell offers extended sizing.

Non-Grunge Mary Janes

If this strappy style brings back bad ‘90s memories of floral baby-doll dresses and torn fishnets, take another look. Coming in everything from black patent to velvet to sparkles, and balanced on a stack heel, they’re grown-up and sophisticated. Urban Outfitter’s version lets you get the look at a bargain, while Miu Miu’s comes straight from the runway.

Boss-Lady Pumps

A powerful wardrobe includes heels that say you’re a force to be reckoned with. The standard pump is always a safe bet, but strappy styles have an extra boost of attitude. Zara’s bright-red style conveys confidence while Manolo Blahnik’s beige patent pair has a subtle strength.

Evil-Looking Ankle Boots

These are the boots you imagine Carine Roitfeld wearing with a sleek pencil skirt while she’s running the show. They’re sharp, mean-looking, and a little dominatrix-y. Jeffrey Campbell’s collab with Revolve plays up the S&M aspect, while Alexander Wang adds textural contrast in the form of haircalf.

Super-Fun, Fancy-Looking Shoes

Spring has a better rep for being filled with wacky, colorful shoes, but just because you have to cover your toes in fall doesn’t mean you have to be boring. These styles can make any outfit special. Loeffler Randall updated its Pari pump with a swishy fringe trim while Gucci’s low sling-back heel has a gold heel dotted with gems.

A Non-Boring Menswear Shoe

Women who want masculine styles usually buy lace-up oxfords or loafers, but it’s time to consider the monk strap. Topshop’s rich-green version pairs well with tweed trousers, while Aquatalia’s shiny Bordeaux patent pair contrasts nicely with a sweeping midi skirt. And if you want to splurge, Dries van Noten’s blue platform pair is a standout.

The Jolie-Laide Shoe

These are divisive heels: Most people hate them, but the women who love them really LOVE them. Céline is the queen of the so-wrong-it’s-right heel, but Rachel Comey and Jeffrey Campbell both offer the same feel at more modest prices.

Street-Style-Worthy Booties

Chances are good that if someone took your photo at Fashion Week, you were wearing either Louis Vuitton wood-heeled booties or Dior’s Lucite ones. For those who have an inner Golden Peacock dying to spread her feathers, these are the ankle styles to get. Zara’s take has the same see-through accent, while Reiss features a gold-trimmed, dark-wood heel.

The 50 Chicest Shoes to Wear This Fall