8 Fresh Ways to Wear Ankle Boots

At first, we thought they were a passing fad. Like fro-yo or Ryan Lochte. But after several seasons of monopolizing the footwear department, ankle boots have proven their staying power. In search of new ways to wear them this fall, we turned to our favorite street style stars for inspiration.

1 of 10
  • White denim, frilly frocks, Bermuda skirts, midi skirts. The combinations are practically endless. Click through our slideshow of easy-to-replicate looks. Note: Do try these at home. 

  • Nicole Warne of Gary Pepper Vintage
    Photo credit: Imax Tree

    Nicole Warne of Gary Pepper Vintage

    Now this is how you wear white after Labor Day. Note how the hem of her white jeans hits right above her Charlotte Olympia ankle boots? The result is a slick, tailored look we love.

  • Blair Eadie of Atlantic Pacific
    Photo credit: http://atlantic-pacific.blogspot.com

    Blair Eadie of Atlantic Pacific

    In keeping with the dressy vibe, polish off a fitted, ladylike Clover Canyon Printed Neoprene Jacket ($374) and Neoprene Skirt ($242) combo with pointed toe Tibi Piper Boots ($598). 

  • Danielle Bernstein from We Wore What
    Photo credit: http://weworewhat.com

    Danielle Bernstein of We Wore What

    They’re baaaaack. To adapt Bermuda shorts or culottes—specifically, by Giulietta, paired with a Topshop sweater—to the 21st century, skip the Birkenstocks and opt for chic leather Cheap Monday Cube Pointy Toe Booties ($155).





  • Margarita on Caroline’s World
    Photo credit: Stockholm Street Style

    Margarita on Caroline’s World

    The Zara shoe’s chunky heel and Western cut help anchor an otherwise flowing and feminine ensemble.

  • Silvia on Street Peeper
    Photo credit: Phil Oh (http://streetpeeper.com)

    Silvia on Street Peeper
    Balance a flirty ensemble like this cropped Sonic Youth t-shirt and pencil skirt with a directional oversized jacket and (le sigh) sold out Maison Martin Margiela Split Toe Tabi Boots for a look that exudes casual cool.



  • Zina Charkoplia of Fashion Vibe
    Photo credit: http://www.fashionvibe.net

    Zina Charkoplia of Fashion Vibe

    Toughen up a doily of a dress (Zara) with shiny black boots (also Zara) and a Proenza Schouler PS11 Tiny Bag ($1425) to match.


  • Andy Torres of StyleScrapbook
    Photo credit: http://stylescrapbook.com

    Andy Torres of StyleScrapbook

    A substantial shoe—Zara again, in this case—subverts the inherent sexiness of short Sandro shorts. Daisy Duke, this is not.  

  • Elsa Ekman on Caroline’s Mode
    Photo credit: Stockholm Street Style

    Elsa Ekman on Caroline’s Mode

    We’ve never met a fringe detail we didn’t love and these Gina Tricot suede boots are no exception. They soften up this sporty Nowhere dress/Mango sweater combo and give it a boho twist.


Today On: