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 manytimes 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 almost September, after all.)
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.
Set to be the most versatile item in your wardrobe.
Those thick lug soles are everything.
Just look at the extreme square toe on this COS pair.
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).
Sometimes simple is best.
Fact: Ganni’s footwear is always worth the investment.
This heel is low enough for everyday wear.
Style notes: Mary Janes are having a moment, and I love 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.
Sport with bare legs in the summer and thick tights when autumn rolls around.
Shoes that won’t go out of style.
White pumps scream 1960s to me.
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.
A black midi will work with any shade of boot. Yes, even navy.
The proportions are perfect on this pair.
This wider heel looks super comfortable to walk on.
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 facile. A colourful kick will cheer you up on those rainy autumn days.
Wear casually now, formally later.
Who says pastels are only for spring?
A pop of mint to liven up your look.
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.
You can make this dress suitable for every season with a few accessories changes.
Tackle those icy pavements with these stylish stompers.
