10 Dress-and-Boot Combos That Work Every Time

If you can find a more iconic fashion duo than the humble dress-and-boot combo, do tell. This pairing is so easy to fall back on right now when the seasons have changed and we’re still remembering how to get dressed for it. It couldn’t be better for the crazy weather we all seem to be having, with torrential rain one minute and crisp blue skies the next. Sandals are a no-go anymore (unless you want frozen toes on the way to work), so boots it is. When you’re sweating on the bus home, you’ll be thankful for a floaty dress.

We’ve already spotted some of our favourite influencers wearing excellent dress-and-boot combinations, which inspired us to start the shopping list below. Although you can be pretty safe in the knowledge that most boot styles go with most dresses, these street style looks might just inspire you to leave your comfort zone and try a new pairing this season. I’m on the lookout for the perfect black chunky pair to go with the minidresses I keep lusting after. Midi dresses were made for knee-high boots, and longer maxi styles work excellently with statement ankle boots. Why not throw glittery cowboy boots into the mix like Megan Ellaby has?

Keep scrolling for more inspiration and to shop the best styles.

Style Notes: Jessie’s patent Prada boots and check dress are what grunge should look like in 2019. 

Style Notes: Florrie’s ruched beige Totême dress is anything but boring and feels really autumnal paired with burgundy Rejina Pyo boots. 

Style Notes: We’re crushing on Bettina’s yellow-and-blue pairing here. The prairie-style dress works so well with pointed-toe croc-embossed boots. 

Style Notes: Buckled boots always toughen up a floral dress. Lisa’s layered look is inspiring us for the colder weather. 

Style Notes: This outfit makes us feel happy just looking at it. We’re loving how these glittery boots change up a floral dress. We’d also wear them with a knitted dress to the pub this winter. 

Style Notes: We’ll never say no to an animal-print dress. Monikh styles her perfectly with a quilted puffa and lace-up chunky black boots. Forever our style inspo.

Style Notes: Nanushka is always a winner for dresses. Alexis Foreman keeps it clean and simple with this long style. We love that she pairs it with classic black ankle boots. You can’t go wrong here. 

Style Notes: This Cefinn pinstripe-dress–and–black-suede-boots combo is giving us all the autumn office inspiration. Just throw on a camel coat and you’re set. 

Style Notes: Hajra shows us that knee-high boots and a floral maxi dress are a winning winter combination if we’ve ever seen one. 



Style Notes: As Jeanette Madsen proves, the best way to make a formal maxi dress daytime appropriate is it pair it with chunky flat boots and your favourite mini bag.