The Dress-and-Boot Combos That Work Every Time

October 17, 2020 at 06:31AM

If you can find a more iconic fashion duo than the dress-and-boot combo, do tell. This pairing is so easy to fall back on right now when the days are shortening and the weather is dull so we’re not able to get as creative with our wardrobes. Grab a go-to dress, throw on a pair of sheer tights and your favourite boots and you’re ready. 

We’ve spotted some of our favourite influencers wearing excellent dress-and-boot combinations recently, 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 balance out the feminine maxi dresses I’m lusting after this season. Midi dresses were made for knee-high boots, and longer maxi styles work excellently with statement ankle boots

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

Style Notes: When in doubt, keep it simple with a cute pie crust mini dress and chunky boots.

Style Notes: We couldn’t not include Enis’s mint jumper dress and knee-high boot combo. If these boots make all legs look this good, we’re sold. 

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: 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: 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.  

Style Notes: This is one of those wear anywhere, lasts for seasons dresses that only come along once in a blue moon. Karina makes it winter 2019 appropriate here with Mint Velvet’s hiking boots. 

Next, read our autumn/winter trend guide.

Promo image: @y.a.t.r.i

Author Emily Dawes | Whowhatwear
Selected by CWC

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