A Slouchy Boot Is an Autumnal Wardrobe Hero

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We all recall the viral moment Saint Laurent debuted its $10,000 rhinestone-covered slouchy boots for fall 2017. You know, no big deal. Maybe it’s Rihanna (it’s definitely Rihanna), or perhaps it’s our penchant for nostalgic designs, but slouchy boots like that standout runway pair are back again—and they’re fall’s winning shoe style to splurge on. If you’re not keen on dropping five months’ worth of paychecks on sparkles, the best slouchy boots cover a much wider range, from Rag & Bone and Staud to Marc Fisher and Khaite.

The slouchy boot made its first waves in Vivienne Westwood’s pirate-inspired ’80s collection, then was embraced in the early ’90s and 2000s by off-duty supermodels like Kate Moss. With this history, it’s no surprise slouchy boots are returning: The fashion industry constantly references past styles, particularly in footwear. Designer Manolo Blahnik thinks it’s because of the vibe of decades past—everything was fresh. “Supermodels, extravagant fashion shows, collaborations. There was such a buzz in the industry, and people were very experimental with their style,” Blahnik explains. “I created shoes for Isaac Mizrahi’s shows throughout the ’90s, and we had so much fun! There was a vibrant energy in the air that perhaps is not around as much today.”

While fashion’s energy is constantly shifting, reemerging shoe styles—like slouchy boots and Mary Janes—are making us feel excited again. “A slouchy boot can completely change the way you look and feel about an outfit. It sits between casual and formal, yet always remains classic and sophisticated,” Blahnik says. To keep your slouchy boot classic, his label’s Calasso styles are our top recommendations. If you’re looking for a slouchy boot that will turn heads and start conversation, Loewe has a particularly epic over-the-knee pair (which also comes in a lower-profile silhouette). For an everyday style, opt for Paris Texas—the label’s slouchy boots range from deep purple to ’90s-inspired denim.

For all of your styling pleasure, both for end-of-summer and cold-weather looks, shop the 20 best slouchy boots on the market ahead. Each pair was chosen based on its silhouette, materials, and heel height, plus expert insight.

Calasso Slouchy Boots

Manolo has taken influence from feminine details and utilitarian styling to create a series that can be worn throughout every season. With its almond toe and walkable high block heel, it’s clear the Calasso is an everyday boot to invest in.

“The Calasso style is the perfect slouchy boot. I had taken inspiration from utility styling, and it comes in a range of different colors and textures, like leather and suede, and hits mid-calf," Blahnik says. “[It is] a simple silhouette that is subtle and practical.”

Sizes: 3–13

Heel height: 3.5"

Mila Olive Calf Boots

Inez creative director Hannah Spinelli loves to mix and match aesthetics when wearing the Mila boots. “Lately I’ve been wearing our Mila boot under a loose-fitting midi slipdress that has side slits,” she says. “I love the unexpected contrast of delicate silk with the substance of a slouch boot. It feels right in line with the current ‘wrong shoe theory.’”

Sizes: 6–10.5

Heel height: 2.8"

Toy Over-the-Knee Boot

For a slouchy boot that is anything but typical, look to Loewe. The Toy boot is crafted in soft Napa lambskin and features the details of Loewe’s classic five-pocket trouser design. Wear them with knitted two-piece sets or denim.

Sizes: 5–11

Heel height: 3.7"

Angora 85 Slouchy Boots

Don’t you want every color in Paris Texas’s boot collection? Available in this creamy white, blue, black, and lavender, these classic slouchy boots have all the markings of a go-to shoe style for the colder months.

Sizes: 5–12

Heel height: 3.3"

Brea Slouch Boot in Blush

Not all slouchy boots are over-the-knee or knee-high—case in point: Rag & Bone’s Brea boot. Designed in soft blush, it has a pull-on, sock-style silhouette with a pointed toe that will look sophisticated poking out from beneath wide-leg trousers.

Sizes: 6–9

Heel height: 3"

Wally Suede Knee Boots

Staud knows what the girls want—and what they want is to feel hot and comfortable, simultaneously. The Wally boot will quickly become a favorite with its western edge, low heel, and extra long pointed toe.

Sizes: 5–12

Heel height: 2"

Marfa Leather Over-the-Knee Boots

With a Matrix-inspired disposition, Khaite’s Marfa boots are here to elevate your wardrobe essentials. From denim, T-shirt, and maxi dress pairings and beyond, the over-the-knee style is punctuated by square toes and a slanted block heel—markers of a Khaite shoe.

Sizes: 6–11

Heel height: 1"

Galley Boot

Revitalize layered looks with this Marc Fisher boot. With a slouchy silhouette and a pointed toe in a fully solid hue, this boot is made to mix and match with seasonal favorites.

Sizes: 6–11

Heel height: 3.8"

Zodiac Riau Slouch Pointed-Toe Boot

Made from cream-colored faux leather, the Zodiac boot is one to covet and embrace with other neutral separates. It’s balanced by a pointy toe and stacked block heel for all-day strutting, browsing, and dancing.

Sizes: 5–11

Heel height: 2.5"

Jahleel Denim Boots

Amina Muaddi—a Jordanian-Romanian accessory designer routinely making waves—is behind the Jahleel boot, and you can tell by its construction. It has an edge to it, with a trendy flair, and is made from denim with a classic stiletto heel.

Sizes: 6–11

Heel height: 3.75"

90 Suede Over-the-Knee Boots

Alaïa released several must-have accessories on its Spring 2023 runway, and these boots were among them. Versatile and ageless, they work just as well with LBDs as they do with maxi dresses.

Sizes: 5–11

Heel height: 3.5"

Sealed With a Kiss Slouch Boot

For those hunting for a pair that oozes the sensibilities of the past, look no further than this option fro Seychelles. A knee-high silhouette, grainy leather, and a classic almond toe take me right back to the ’00s.

Sizes: 6–10

Heel height: 2.4"

Slouchy Leather Ankle Booties

Modernize the slouchy boot trend with Reike Nen. The designer’s latest collection features a low-profile ankle bootie with the same scrunched leather. Show off the sharp toe with a sweeping hemline.

Sizes: 6–10

Heel height: 2"

Denim Sleeve Cowboy Boots

This isn’t your classic slouchy boot—actually, it’s anything but. For a playful, on-the-nose western tone, look to R13. Designed to resemble a denim-covered leg, these sleeved slouchy boots can be worn with the basics. Better to let them shine.

Sizes: 6–11

Heel height: 2.25"

Tabi Leather Western Boots

The Tabi split toe is inspired by the traditional 15th-century Japanese sock bearing the same name, and you’ll see it throughout Margiela’s collections. This western boot is no different. The boots are made of calf leather and feature an almond-shaped split toe.

Sizes: 5–11

Heel height: 2.1"

Black Bridge Boots

The Bridge boots from Coperni also have a western edge, but in a totally contemporary way. A sculptural block heel and mid-calf height make them the ideal option for Bermuda shorts or midi dresses.

Sizes: 6–11

Heel height: 3.25"

Naomi Lambskin Slouchy Platform Boots

Edgy. Modern. Sleek. The Naomi boots remind me of an off-duty model at the peak of street style’s first surge. An impressive block-heel platform defines this style—ideal to be worn with matching sets and sharp tailoring.

Sizes: 5–10

Heel height: 3.5"

Ashlee Soft Nappa Bootie

What says the early ’00s like a bootie with a wedge heel? Schutz is known to be comfortable, so expect the Ashlee bootie to feel like a tall sock. Show off the heel shape with a flouncy bubble hem skirt.

Sizes: 5–11

Heel height: 4.3"

The Cady Boot

If you have yet to hear of Dee Ocleppo, prepare to become obsessed. (I know I did.) The brand was founded by Ocleppo, a former model, creative director of Judith Leiber, and wife of Tommy Hilfiger. These slouchy boots are made in Italy from brown Napa leather with a pointed toe and a sculptural wedge heel. They’re sure to be the first of many you shop from the brand.

Sizes: 5–11

Heel height: 3.9"

Vegan Suede Slouchy Boot

Fashion insiders are absolutely here for Banana Republic’s resurgence—all of the latest collection drops are brimming with must-have accessories, luxe separates, and high-quality fabrics and materials. Just take a look at these slouchy boots, made from lush suede in a burnt orange.

Sizes: 6–10

Heel height: 3.5"

Meet the Experts

• Manolo Blahnik is the creative director and chairman of his eponymous luxury footwear label.

• Hannah Spinelli is the creative director of footwear label Inez.

• Cortne Bonilla is a fashion writer and editor whose work appears in Bazaar, among other outlets.

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