These 6 Autumn-Ready Shoe-and-Dress Combinations Work Every Time

I'm a creature of habit, particularly in the clothing department. With the arrival of each season, I gaze wide-eyed at the constant stream of newness landing in my inbox, saving inspiration from brands and influencers for cool outfits to try. Yet within weeks, I fall back into old patterns. Instead of reaching for the same strappy sandals to chuck on with a well-worn pair of jeans that are perfectly moulded to my body, I choose a classic boot and chunky cardigan to fit the bill. The denim probably stays.

When I'm not testing the boundaries of how many times is too many times to wear the same jeans in a week, you'll likely find me in a mini or midi dress. And come autumn, I'll be donning my favourites almost exclusively with boots. Chelsea, knee-high, Western—it doesn't matter, as long as they come past the ankle and keep my feet warm.

In an effort to break this unimaginative loop, I've decided to source some alternatives. It turns out there are a lot of strong shoe options on offer right now, from thick-soled loafers to dainty Mary Jane pumps. Enthused by this discovery, I also thought it worthwhile to decipher which shoes work best with which dress type. Scroll for fresh footwear to style with your reach-for dresses. Warning: There are still a few pairs of boots in the mix. (It is October, after all.)

1. Chunky Loafers + Slip Dress


(Image credit: @lucywilliams02)

Style Notes: There's something so chic about balancing the heaviness of a chunky loafer with the fluidity of a slip dress. I love how Lucy Williams has kept the edge by adding a leather blazer over top.

2. Heeled Boots + Knitted Midi


(Image credit: @laurennicolefk)

Style Notes: The number one priority in the colder months? Staying cosy. A knitted dress will do the job, elevated with a sleek pair of heeled boots (that doesn't compromise on comfort, of course).

3. Mary Janes + Minidress


(Image credit: @bubblyaquarius)

Style notes: Mary Janes are having a moment, and l'm into how they look with cutesy minidresses—the more voluminous, the better. Wear opaque tights for a winter-friendly spin on this '60s-tinged look, and add a beret if you want to go full-on French girl.

4. Knee-High Boots + Patterned Midi


(Image credit: @katherine_ormerod)

Style Notes: We're used to seeing knee-high boots worn with short dresses, but I'm a huge fan of this new combination. Personally, I'll be opting for a heeled boot with a slightly pointed toe to elongate my silhouette—particularly important when there's no leg on show.

5. Retro Trainers + Tiered Maxi


(Image credit: @fiahamelijnck)

Style Notes: A sure-fire way to make your frilly maxi dress more wearable? Slip on some trainers; they'll stick out from the bottom and bring your outfit from fancy to fuss-free. A colourful kick will cheer you up on those rainy autumn days.

6. Lug-Soled Boots + Cotton Dress


(Image credit: @emmarosestyle)

Style Notes: This is a great way to carry your whimsical summer dresses into autumn and make them year-round appropriate. I adore the juxtaposition between feminine and combat styles, too. Keep a cardigan handy in case this natural fabric is a little bit too breathable in the British wind.

This story was published at an earlier time and has since been updated.

Up Next, I'm a Stylist—7 High-Street Brands I Always Rely on for Expensive-Looking Boots

Freelance Fashion Editor

Bébhinn Campbell is an Edinburgh-based fashion and lifestyle writer and editor. She started her first blog at age 14 and went on to intern at print and digital publications in Berlin and London, including Dazed & Confused and Indie magazine.

A job at a fashion startup took Bébhinn from Ireland to Scotland in 2019, where she now works as a freelance journalist and copywriter covering everything from travel and interiors to styling advice. As a contributor to Who What Wear, Bébhinn always keeps her eyes peeled for emerging trends and looks worth writing about. She prides herself on her ability to cut through the noise and identify solid investment buys, exciting new brands and fresh takes on classic design.

In her spare time, Bébhinn enjoys perusing Edinburgh’s best vintage shops, working through her out-of-control book collection and watching dog reels on Instagram.