8 Fall Dresses to Wear With Ankle Boots

last updated 13 August 2019

When it comes to fall dressing, here’s no easier or more effective outfit than the old dress-and–ankle boots combo. Whether you’re off to Sunday brunch, a concert, or a night out on the town, the right pairing can have you covered for anything. So in honor of the new season, today we’ve done the work for you and paired eight standout dresses with eight equally amazing pairs of ankle boots for you to shop or simply draw inspiration from. Whether you're a mini, midi, solid, or print girl, we've got (at least) a look for you.

Shop the outfits below and be sure to let us know which you'll be trying first in the comments!

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SHOP: Dôen Paix Dress ($285) + Acne Studios Caroline Snake-Effect Leather Ankle Boots ($700)

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SHOP: Altuzarra Winne Asymmetric Paisley-Print Silk Maxi Dress ($2995) + Topshop Martini Zip Front Boots ($135)

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SHOP: Ganni Satin Maxi Dress ($240) + Aquazzura Baroque Velvet Ankle Boots ($745)

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SHOP: Cotton Citizen Milan Cut Off Dress ($245) in Olive x Isabel Marant Danae Velvet Ankle Boot ($790)

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SHOP: Topshop by Boutique Hybrid Mix Print Dress ($160) + Proenza Schouler Leather Ankle Boots ($995)

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SHOP: Isabel Marant Bremen Long Sleeve Mini Dress ($1035) + Mango Patent Sock Boots ($100)

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SHOP: Joseph Cashmere 12gg Amma Dress in Camel ($705) + Gucci Fringed Suede Ankle Boots ($1100)

Love this dress? Check out our sweepstakes for the chance to win a prize from Joseph!

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SHOP: Zara Floral Dress ($70) + Miu Miu Fur-Heel Suede Ankle Boots ($890)

Which combo will you be trying first? Tell us in the comments!

Opening Image: Collage Vintage

Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.