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

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.

At Refinery29, we’re here to help you navigate this overwhelming world of stuff. All of our market picks are independently selected and curated by the editorial team. If you buy something we link to on our site, Refinery29 may earn commission.

Irina Grechko, Fashion Director

"I love the feel of silk slip dresses and refuse to pack them just because it's fall or winter. Instead, I style them over turtlenecks and button-down shirts as soon as the temperatures start dropping. To protect my skin against itchy coat fabrics, I often double up on soft textures, pairing a silk dress with moldable suede thigh-high boots."

Brochu Walker The Everyday Silk Slip Dress, $, available at Brochu Walker

Stuart Weitzman Highland Block Heel Suede Over The Knee Boots, $, available at Saks OFF 5TH

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 colour palette screams long walks, crunching leaves, listening to Taylor Swift on repeat and romanticizing my life with a large coffee."

Realisation Par The Iggy in Saffron, $, available at Realisation Par

Zara Star Leather Cowboy Boots, $, available at Zara

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."

Maje Tweed-Effect Dress, $, available at Maje

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

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."

ASOS DESIGN Cotton Pleated Bust Midi Babydoll Sundress, $, available at ASOS

Topshop Wide Fit Hattie Platform Sock Boot, $, available at ASOS

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

"I've pared back my wardrobe significantly this year, only choosing new pieces that I know I'll want to pull multiple times a week. This drop-waist maxi dress from ASOS has been a star staple for me since I nabbed it a couple of weeks ago. The ribbed top is super stretchy and comfortable, while the skirt makes me feel like I've dressed up more than I actually have. Here I've layered it over a sheer vest and my year-old Miista boots. While this style is now sold out, there are still plenty of similar options in stock."

ASOS DESIGN Ribbed Scoop Neck Midi Dress With Dropped Waist, $, available at ASOS

Miista Inne Brown Boots, $, available at Miista

Breanna Davis, Associate Social Editor

"Wearing thigh-high black boots with this summery dress made me feel super sexy; the thigh-high slit gave enough leg to peek-a-boo when I walked. I was channeling a ladylike dominatrix, and I loved it. My exact dress is sold out, but there are plenty of options out there."

UO Arna Midi Slip Scoop Neck Dress, $, available at Urban Outfitters

Aldo Nella Over-the-Knee Boot, $, available at Aldo

Vagabond Shoemakers Tara Platform Boot, $, available at Nordstrom

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

Like what you see? How about some more R29 goodness, right here?