How to Wear Ankle Boots, According to a Stylist

Gabrielle Ulubay

September 15, 2022 at 1:32 PM·4 min read

Influencer and model Marlies Pia Pfeifhofer wearing a 70s suit by Tory Burch, a white turtleneck pullover by Allude, sunglasses by Lanvin, ring and earrings by Ole Lynggaard, a brown bag by Louis Vuitton and purple high heel booties by Lola Cruz during a street style shooting on January 27, 2022 in Munich, Germany.

Now that the weather is cooling down and fall is just around the corner, it's time for all of us to put away our sandals and break out our very best boots. Personally, boots are my favorite type of shoe, and when it comes to the most versatile style for everyday wear and for transitioning into autumn, I always go for ankle boots. I'm not alone: Fashion stylist Sarah Nearis also loves a good ankle boot, calling it her "personal favorite" and defining the style as one that "covers the whole foot and reaches up to or a little past the ankle."

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

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

With Trousers

A guest wears black sunglasses from Dior, silver rhinestones fringed pendant earrings, a white checkered print pattern / asymmetric cut-out oversized shirt, gray large suit pants, a dark brown matte leather handbag, black shiny varnished leather slit / split toe-cap block heels ankle boots, outside Rabens Saloner, during Copenhagen Fashion Week Spring/Summer 2023, on August 09, 2022 in Copenhagen, Denmark.

For a polished look, Nearis recommends styling your ankle boots with a high-quality pair of trousers. "I love pairing a pointed toe heel bootie with a great trouser or suit," she says. I, too, love this look, and find that ankle boots' short height lends itself to being worn with a pair of tailored pants.

Everlane The Boxy Oxford

Farm Rio Dotted Macaws Organic Cotton Bodysuit

Athleta Nolita Wide Leg Pant

Open Edit Wide Leg Suit Trousers

Madden Girl While Boot

Alfani Step N' Flex Women's Jacklynne Pointed-Toe Dress Booties

With a Suit

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

As Nearis said, ankle boots look fabulous with a pair of trousers or with 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 opting for a "classic heel" to give you a height boost and add a feminine touch to a potentially androgynous look.

Ann Taylor The Notched Two Button Blazer In Cross Weave

Ann Taylor The High Waist Slim Ankle Pant In Cross Weave

Victoria Beckham Woven Blazer

Victoria Beckham Woven Straight-Leg Pants

Sam Edelman Wrenley Bootie Heel

Kelly & Katie Aveya Bootie

With a Slip Dress

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

A slip dress is one of the ultimate fall staples, no matter what the season is. Its simplicity allows it to be paired with a number of accessories and shoe styles, including the ankle boot. Nearis says that she loves pairing her Western boots with slip dresses, in particular. Personally, I'm a devotee of the lace-up ankle boot, and love embellishing the slip dress with a flash of yellow gold jewelry.

Intimissimi Midi-Length Slip in Silk

Bebe Solid Satin Bias Slip Dress

Isa Noy Coco Lover Hand Chain

Child of Wild Star Dust CZ Necklace

Isabel Marant Dewina Western Boot

Dr. Marten's 1460 Boot - Women's

With Leather

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

Many ankle boots are already made of leather, but Nearis says you should consider adding leather elements or accessories to bring out your boots or toughen up an otherwise ultra-feminine outfit. For instance, she says loves throwing a leather jacket over her slip dress when she wears it with boots. You can also pair the boots with leather pants, jewelry, or hair accessories―the possibilities are endless.