The #1 Dress-and-Boot Combo for Colder Weather

Much like everyone else, I want a super-simple way to get dressed in winter so I can stay under the warm covers as long as possible. My solution? Ankle boots and dresses. But how do you make them seem interesting every day? Plus, there are so many different types—how do you know which variations go together? After taking cues from street style looks, I've managed to narrow down five key combos that are ideal for those who just want to wear ankle boots and dresses every day during the colder months. Spoiler: If you follow this advice, you'll get more sleep in the mornings, so it's a win-win, really. Keep scrolling for tips on how to wear ankle boots with dresses.

#1: Minidress + biker boots

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Style Notes: A short knitted dress is vital in winter, but if you want to avoid feeling too dressed up, then add a pair of biker boots to give your outfit an edge. Wear with tights if it's really cold.

#2: Wrap dress + matching boots

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Style Notes: There's nothing more flattering than a wrap dress, but instead of thinking that it only works with sandals in the summer, pick out a colour in your dress (if patterned) and match with coordinating boots.

#3: Dress over jeans + bold boots

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Style Notes: Yasmin Sewell's take on the dress-and–ankle boots combo is to layer it over jeans. Lucky for us, this is still a winning formula right now, not to mention it's super practical for the winter.

#4: Tulle dress + striking boots

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Style Notes: Pretty, frothy dresses from the likes of Needle & Thread can be toughened up with a pair of bold boots. We like yellow, but red, purple, or green would work just as well.

#5: Shirtdress + smart boots

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Style Notes: Shirtdresses are one of the easiest wins for the office, whether it's summer or winter. To make yours as smart as possible, opt for a pair of boots with stiletto heels and go for a dress with sleeves.

Want more? Check out the 41 ankle boots we've loved (and shopped) this season.

Elinor Block