Our Editors Think These 4 Boots Go With Every Dress They Own

We all have that one pair of favourite boots. If you’re lucky you might even have a couple. The ones you get out year after year and pull on in the morning half way out of the door when you’re late for work, because you just know they go with everything. We got to thinking in the office about what our ‘desert island boots’ would be and we all landed on pairs loved because they went with literally all of our dresses, as well as with jeans and knits at the weekend

But what happens when those beloved boots fall apart or you're desperate to try a new trend? It’s tough to believe you’ll ever love another pair in the same way. We get it, the stakes are high when autumn rolls around again and it’s time to take the plunge and pick a new pair - buying boots is an investment and a risky one at that. What if they give you blisters and never wear in? Are they going to be slightly too high to walk to the train station in? That’s why, with dress-and-boot season well and truly upon us, we thought what better way to celebrate than to give our favourite boots a piece of the limelight and share with you why we love them so much - so you can too. 

From chunky hiking boots that toughen up pretty dresses to the ultimate knee-high style that not only look good, but keep your legs toasty too. Keep scrolling to see what we picked, what we wear them with (all the time), and to shop them now.

Elinor Block: 

Style Notes: "I bought these ASOS boots nearly a year ago when it was freezing and I was slipping all over the place during the winter. So far these have weathered plenty of snow and ice, and are currently getting me through lots of mud and rain, all the while keeping my feet bone dry. The slightly patent finished means they also look a little fancy and work with any dress in my wardrobe. Total winners." — Elinor Block, assistant editor

Shop Elinor's Look:

Joy Montgomery:

Style Notes: "I bought these boots from Zara two years ago now and they've honestly been such a godsend during the winter months. They're actually thigh-high, but I tend to wear them with longer dresses and skirts (ideal for work), however, I can also roll them down to knee-height if I fancy styling them with a shorter hemline. I love the slouchy fit, unusual heel shape and comfortable round toe—but the best thing? They're the ultimate secret layer when it's freezing outside." — Joy Montgomery, shopping editor

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Emily Dawes:

Style Notes: "I got my hands on these Charles and Keith boots a couple of winters ago when western style boots were just starting to be seen everywhere. Luckily the trend took off and they're now my favourite boots to wear with everything. They go really well with midi-dresses like this Ghost number for work but also look great with a mini-dress for dinner with the girls. You're in luck, this exact style is still for sale in the grey - I'm seriously considering investing in a second pair for this year." — Emily Dawes, contributing editor

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Alyss Bowen:

Style Notes: "I wanted these boots well over a year ago but no matter how hard I tried, I couldn't get my hands on them. Fast forward to this September and as soon as I saw them back in stock, I snapped them up. I've probably worn them every single day since purchasing them and they go with everything—from jeans and a jumper to pretty floral dresses to toughen them up a bit. It's safe to say I'll be wearing them for years to come." — Alyss Bowen, associate social media editor

Shop Alyss's Look:

Up next: See our favourite dress-and-boot combos worn by influencers.