10 Dress-and-Boot Combos That Work Every Time

Emily Dawes

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 mornings are dark 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. Always appropriate for the office, but also for those weekend drinks commitments you oversubscribed yourself for. 

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. Why not throw glittery boots into the mix, as Megan Ellaby has?

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

Style Notes: We couldn’t not include Lizzy Hadfield’s LBD and Jimmy Choo combo. So simple but so effective for party season. If these boots make all legs look this good, we’re sold. 

See By Chloé Tiered Lace Mini Dress (£340)

Jimmy Choo Mahesa 100 Cuoio Calf Leather Knee High Boots (£1295)

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

Preen By Thornton Bregazzi Brianna Checked Draped Chiffon Dress (£1370)

River Island Black Chunky Patent Boot (£42)

Le Specs Outta Love Oval-Frame Tortoiseshell Acetate Sunglasses (£40)

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

Topshop Cream Open Back Midi Dress (£29)

Rejina Pyo Ashley Leather Knee-High Boots (£825)

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. 

Rhode Harper Shirred Floral-Print Cotton Midi Dress (£336)

Topshop Maeva Blue Flared Boots (£89)

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

Ganni Kochhar Floral-Print Silk Crepe De Chine Maxi Wrap Dress (£275)

Chloé Susanna Studded Leather Ankle Boots (£850)

Autograph Wool Silk Blend Tailored Blazer (£99)

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. 

Essentiel Antwerp Floral-Print Belted Midi Dress (£230)

Miu Miu Glitter Embellished Ankle Boots (£615)

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.

H&M Tie-Belt Dress (£25)

Russell and Bromley 8 Eyelet Combat Boot (£225)

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. 

Nanushka Ballon Sleeve Knit Dress (£190)

Dear Frances Spirit Boot Black (£520)

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. 

Cefinn Thea Handkerchief Hem Shirtdress (£350)

& Other Stories Knee-High Suede Boots (£205)

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. 

New Look Black Floral Long Sleeve Maxi Smock Dress (£30)

Gucci Suede Belt With Torchon Double G Buckle (£225)

La Redoute Suede Heeled Boots (£95)

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.  

Rotate Birger Christensen Open-Back Floral-Print Crepe Maxi Dress (£294)

Dr. Martens 1460 Lace-Up Textured-Leather Ankle Boots (£140)

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

Kitri Joy Pink Check Tea Dress (£125)

Mint Velvet Janny Black Hiking Boots (£159)

Style Notes: If you like a pop of colour in your wardrobe, this bright midi makes a nice change from all the minimalist neutrals we’re seeing at the moment. As Eni shows, just add classic suede boots and this dress can come with you to the office all year round. 

Preen Line Esme Floral-Print Pintucked Maxi Dress (£495)

& Other Stories Knee High Suede Boots (£205)

Next, read our autumn/winter trend guide.

This article originally appeared on Who What Wear

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