These Are The Best Dress & Boots Combos According To R29 Editors

Photo: Courtesy of Ebony-Renee Baker.
Now that it's officially autumn, our wardrobes are reflecting the shift in temperatures — and for the fashion girlies, it's a welcome one. We're talking sweater weather, seasonally flavoured hot drinks and an urge to stay inside and stream our favourite comfort shows. But arguably one of the most exciting parts of autumn? Being able to pair boots with dresses comfortably again. Autumn gives us the opportunity to wear our stompers without them feeling like feet saunas, while still being 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 our team about the dress-and-boots combos they’ll be wearing on repeat this season. From comfy midis and structured minis to cowboy boots and knee-high staples, take some pointers from our team on how to wear this season’s breeziest outfit formula.

Irina Grechko, Fashion Director

"I love the feel of silk slip dresses and refuse to pack them just because it's autumn 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."

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."

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 autumn staple in my closet for five 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."

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 autumn 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 romanticising my life with a large coffee."

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."

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 an autumn date-night look."
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