How to wear ankle boots, according to a stylist

Now that the weather is getting colder and fall is just around the corner, it’s time for all of us to put away our sandals and get out our best boots. Personally, boots are my favorite type of footwear, and when it comes to the most versatile style for everyday wear and transitioning into fall, I always choose ankle boots. I’m not the only one: Fashion stylist Sarah Nearis also loves a good ankle boot, calling it her “personal favourite” and defining the style as one that “covers the entire foot and reaches to or slightly past the ankle.”

Nearis also says that ankle boots are one of the easiest types of boots to wear and there are endless fashion possibilities to pair them with. “Ankle boots are so versatile in terms of style and design,” she says, adding that “there are so many ways to style them.”

If you need more outfit inspiration, read on for our stylist-approved tips and tricks to take your ankle boot ensembles to the next level.

With Pants

A guest wears black sunglasses by Dior, silver rhinestone fringe dangle earrings, oversized white plaid/asymmetric cutout shirt, gray wide leg dress pants, brown matte leather handbag dark, one slit / split toe block in black shiny patent leather Heeled ankle boots, outside Rabens Saloner, during Copenhagen Fashion Week Spring/Summer 2023 on August 09, 2022 in Copenhagen, UK Denmark.

For a polished look, Nearis recommends pairing your ankle boots with high quality pants. “I love pairing a pointed toe heeled ankle boot with some awesome pants or a suit,” she says. I love this look too and I find that the small size of the ankle boots lends itself to being worn with tailored pants.

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Farm Rio Dotted Macaws Organic Cotton Bodysuit

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Athleta Nolita Wide Leg Pants

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Open Edit Wide Leg Suit Trousers

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Alfani Women’s Step N’ Flex Jacklynne Pointed Toe Ankle Boots

With a suit

A guest wears blue suit, white shirt, black bag, Dr Martens boots outside Dsquared during Milan Fashion Week Fall/Winter 2022/2023 on February 27, 2022 in Milan, Italy.

As Nearis said, ankle boots look fabulous with pants or a suit. After all, if you’re committing to this Abbey Road-inspired look, why not go all the way? Nearis recommends a pointed toe boot but also likes to opt for a “classic heel” to give you a height boost and add a feminine touch to a potentially androgynous look.

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Ann Taylor The Twill Weave Two-Button Notch Blazer

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Ann Taylor The high-rise skinny ankle pant in cross-weave

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Victoria Beckham Woven Blazer

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Victoria Beckham Woven Straight Trousers

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Sam Edelman Wrenley Bootie Heel

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Kelly & Katie Avaya Bootie

With a slip dress

Jacqueline Barth wears sunglasses, a long silky shiny black dress, black leather boots, on July 26, 2021 in Sibiu, Romania.

A strappy dress is one of the must-haves for fall, whatever the season. Its simplicity allows it to be associated with many accessories and styles of shoes, including the ankle boot. Nearis says she loves pairing her western boots with strappy dresses, in particular. Personally, I’m a fan of the lace-up ankle boot and I love embellishing the slip dress with a burst of yellow gold jewelry.

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Intimissimi silk mid-length briefs

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Bebe Solid Satin Bias Slip Dress

Isa Noy Coco Lover Hand Chain

Child of Wild Star Dust CZ Necklace

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Isabel Marant Dewina Western Boots

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Dr. Marten 1460 Boots – Women’s

With leather

Yoyo Cao seen wearing a black oversized leather jacket, black cycling shorts, black cap, red Loewe bag and black lace-up boots on March 04, 2022 in Paris, France.

Many ankle boots already come in leather, but Nearis says you should consider adding leather elements or accessories to make your boots stand out or toughen up an otherwise ultra-feminine outfit. For example, she says she loves to throw a leather jacket over her slip dress when wearing it with boots. You can also pair the boots with leather pants, jewelry or hair accessories, the possibilities are endless.