Come along with me into the wonderful world of dresses, will you? No matter which type of dress is your favourite – from cut-out styles to blazer options, shift and slip designs and silhouettes that are structured or flowy – knowing how to style them is what will give your look that special je ne sais quoi. And it all starts with the shoes, my friends.
Choosing the right footwear might be the biggest styling decision you can make. With so many different hemlines to consider (mini, maxi, midi), there are a lot of pairings to be made. Trainers give a casual vibe while wedges instantly dress up a look, loafers are well-suited to workwear and ballet flats are always comfy. Plus, clogs are big news rn.
We told you, the options are endless, and that's before we've even mentioned boots. A whole category in and of themselves, there are knee-high styles to consider, timeless black ankle options, trending cowboy designs and cool-girl biker boots, too. Hey, even snow boots!
Yep, pairing a dress with boots is one of my favourite styling moments. So, to help give you a little trans-seasonal style inspo I've compiled chic outfit combos that are made for strutting, stopping traffic and posting on the 'gram. As well as teaching you how to wear a dress with boots, I've also taken it a step (heh) further and recreated these looks to make shopping a breeze. New season style, we're ready for you!
Wear a blazer dress with cowboy boots
No matter whether you've been to Taylor Swift's Eras Tour or not, cowboy boots are a trend that will live on. Instead of a rustic feel, you can go for an elevated, monochromatic approach with a blazer dress, long coat, and matching bag. A leopard-print belt will be a special touch to add some pizzazz to the ensemble.
Shop blazer dress + cowboy boots
Wear a shift dress with metallic boots
A shift dress is so easy to wear, especially when it's black (it'll match everything, ya know?). Because it's such a simple style, you can easily do it up with a pair of boots that will grab everyone's attention. Ahem, I'm talking metallic boots!
Shop shift dress + metallic boots
Wear an oversized rugby shirt dress with denim boots
Stripes = automatically chill to me, especially when on a rugby shirt silhouette – bang on trend for the summer of sport we're living through rn. You can look casually put-together and polished in a striped shirtdress and denim boots (for some fab flair).
Shop rugby shirt dress + denim boots
Wear a feminine dress and biker boots
You've likely heard of clashing prints, but what about clashing aesthetics? Drawing attention to a contrasting element in your outfit, like a floaty feminine floral dress paired with tough biker boots, is an instant way to look more expensive as it adds texture. A metallic bag will be a fun piece to finish the look and earn even more style points.
Shop flora dress + biker boots
Nobody's Child White Floral Clover Mini Dress
Wear a structured dress and gold-accent boots
IDK about you, but structured dresses are always a moment in my book. What can take them to the next level is timeless black ankle boots elevated with gold accent detailing. If you're brave enough, pin on a brooch, too. Yes, they're cool again! It's giving very demure, very mindful.
Shop structured dress + gold detailed boots
Wear a leather skirt or dress and slouchy boots
Authentic leather or vegan leather – your pick. Just know you need a leather skirt or dress in your arsenal. Maybe both. It'll be perf for creating a look with slouchy boots. It gives street-style star vibes, trust me.
Shop leather look + slouchy boots
Karen Millen Faux Leather Tie Detail Wrap Midi Skirt
Sosandar Taupe Suede Block Heel Slouch High Leg Boots
Wear a smock dress and animal print boots
You can totally pull off animal print boots. Think of it this way: animal prints like zebra, leopard and snake are made up of neutral colours including black, white, grey and brown, making animal print a neutral in itself! Wear yours with a bright smock dress for extra eyes on you.
Shop smocked dress + animal print boots
Wear a cut-out dress and black boots
Whether you're into lil slivers of skin showing or you're all about baring the most, cut-out dresses are for everybody. Put on some classic black boots to pull the ensemble together.
Shop cut-out dresses and sleek boots
Abercrombie & Fitch One-Shoulder Cutout Maxi Dress
Tarah-Lynn Saint-Elien is the fashion editor at Cosmopolitan, writing weighty and witty stories that run the gamut of gushing over Zendaya to convincing you of everything you need in your closet! She began her journey in the industry with a fashion and faith blog and an internship at Elle about 10 years ago. Since then, she's also served as the style editor at The Haitian Times. The Haitian-American pageant queen is Miss Supranational Haiti 2024, a Syracuse Masters graduate, and the author of three books, including: Claim Your Crown. Follow her on Instagram and TikTok: @iamtarahlynn.
