How To Style Dresses With Boots — R29 Editors’ Go-To Fall Combo

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As the season switches from summer to fall, so does our approach to the day. We’re talking sweater weather, seasonally flavored hot drinks, and an urge to stay inside and watch Netflix. Arguably one of the most exciting parts of fall is the return of being able to pair boots with a statement-making dress. As the temperature finally drops, it gives us the opportunity to wear stomper boots without them feeling like foot saunas, yet it’s still warm enough for dresses (with or without tights). In short, it’s the perfect time for this effortless combo to take precedence in your wardrobe once again.

One of the best things about this look is that — more often than not — you won’t have to buy anything new to rock it. So that’s why we asked editors and writers on our fashion team to give us a taste of the dress-and-boots combos they’re going to be wearing throughout fall. From flowy maxis and structured minis to cowboy boots and knee-high staples, take some pointers from our team on how to wear this season’s easiest, breeziest outfit formula.

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Irina Grechko, Fashion Director

“Blame it on the runways but I’ve recently jumped on the Western boot trend train. While I am not brave enough to go the full, knee-length route in New York City – I have a fairly classic, utilitarian style – I’ve been dabbling with these suede booties. In particular, I’ve enjoyed wearing them with flowy slip dresses which, going further into fall, I will wear over turtlenecks.”

Brochu Walker The Dallas Boot, $, available at Brochu Walker— PAID CONTENT —

Prefer to take a subtler approach to the cowboy boot trend? Opt for a pair of sleek black ankle booties with understated Western details, like a pointed toe and U-shaped shaft collar, that nod to traditional riding boots while still looking modern.

Nine West Ghost Ankle Bootie, $, available at Nine West

Saint Art Haley Dress, $, available at Saint Art

Esther Newman, Affiliate Writer

“I love butterflies and I love cowboy boots so this was a no-brainer for me. I wanted to translate these two pieces (some of my summer staples) into fall so that’s why I layered my dress over this Urban Outfitters jumper. The color palette screams long walks, crunching leaves, listening to Taylor Swift on repeat, and romanticizing my life with a large coffee.”

Free People Rancho Mirage Boots, $, available at Free People

Realisation Par The Cameron in Dazed, $, available at Realisation Par

Vivien Lee, Affiliate Fashion Writer

“I’m always up for anything plaid and when it comes to the details of the dress, I appreciate how the black vegan leather piping complements the buttons and makes the dress pop. Plus, I love how timeless this pairing is and that it gives off Parisian vibes. My boots are the comfiest and most trusted pair that I own as they’ve gotten me through New York City’s snow and brisk winds in past seasons. I envision wearing this laid-back yet preppy ensemble for weekend brunches with friends or as a fall date-night look.”

Looks Like Summer Brianna Knee-High Boots, $, available at Looks Like Summer

Staud Fairham Plaid Dress, $, available at Saks OFF 5TH

Frances Solá-Santiago, Fashion Writer

“I love dresses that feel like a blank canvas and this one’s literally that. It makes it really easy to pair with a wide variety of boots and add a unique take to an otherwise simple dress. These snakeskin boots have been an fall staple in my closet for four years and I just can’t let them go because they’re a classic (and so comfortable!). I plan on wearing this on a day when I can go to the office and an after-work happy hour. I love the work-to-play vibe.”

By Far Becca lace-up leather ankle boots, $, available at mytheresa

ASOS EDITION Cotton twill empire cami maxi dress in white, $, available at ASOS

Ebony-Renee Baker, Fashion Editor

“Since receiving this Kitri dress I’ve worn it at least twice weekly, and it’s been an MVP in my wardrobe. Not only is it majorly comfortable but it also pairs well with trainers, heels, and boots alike. I most love this particular combo featuring my flatform boots, which add a level of edginess that I could never achieve by wearing this dress with more feminine shoes, like heels or loafers. This fall I’ll be pairing this combo with my brown trench coat or my short cream leather jacket. Watch out, y’all.”

Vagabond Shoemakers Tara Platform Boot, $, available at Nordstrom

Kitri Diedre Wavy Checker Ruched Jersey Dress, $, available at Shopbop

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