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How to Wear Boots with Dresses

28/08/2025

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Wondering the best ways to style your favourite dresses with boots? Then look no further! We have put together the ultimate style guide on how to wear boots with dresses.

Whether you are looking at midi or maxi dresses we have included all of the different ways you can create some iconic dress with boots outfits.

Things to remember when styling dresses with boots:

  • Boot to dress style: it may be an obvious one, but what we mean by this is to keep your dress in the same style range as your boots, for example leopard print boots might not be a good match with your smartest dress.
  • Tights or no tights: If the weather allows and the dress code isn’t too formal you can choose whichever works best for you.
  • Mix and match with colour: It’s always best to add some colour to your outfit with either your dress or boots or better yet with a statement bag to tie your outfit together.

Dresses To Wear With Cowboy Boots

Dresses To Wear With Western Boots

Cowboy boots are a trend that is sticking around and are guaranteed to add a bit of a country flare to any dress! Choose between a faux suede or faux leather finish for your cowboy boot look.

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This paisley dress is ideal to wear with cowboy boots this season and the maxi length with the flowy material gives a fun boho look. This is the perfect dress based outfit with cowboy boots that will have you shining with confidence.

Whether you’re going to a rodeo event, or want a comfy outfit for an evening meal coming up, this outfit works for any occasion.

Dress To Wear With Knee High Boots

Boots To Wear With A Midi Dress

A midi dress is where the hem finishes in between your knee and ankle, therefore styling with your favourite pair of boots is easy. Knee high boots are a super flattering choice and are a staple for any winter wardrobe.

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Every girl needs a classic pair of knee high boots in their A/W wardrobe, and these riding boots are the perfect pick. Worn with our cord shirt dress you have a perfectly styled seasonal look that you will be reaching for time and time again.

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Add a fun edge to your dress and boots looks with our patent knee high block boots. With a rounded toe, patent finish, and a side zipper fastening, these boots are set to become your new dream pair of boots.

Wear with a satin dress and finish the look with a clutch bag for a stylish yet comfortable autumnal evening vibe.

Ankle Boots To Wear With Dresses

How To Wear Ankle Boots With Dresses

Look no further than our selection of ankle boots, perfect for styling with dresses. Discover a variety of staple styles from chunky chelsea boots to edgy biker boots, you can find a style you’ll love.

Heeled ankle boots are a simple but effective way to style your dresses. Heeled boots will instantly elevate any outfit and are perfect to pair with a printed chiffon dress for a simple but effective look.

With delicate feminine prints, these dresses will look fab with block heel ankle boots and some accessories to finish off the outfit.

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Another great heeled ankle boot choice are our classy midi size heel boots. With a square point toe, a faux suede finish, and a side zip fastening, these boots will complete any evening look with style and grace.

Flat Boots To Wear With Dresses

Flat ankle boots are the perfect blend of comfort and style, making them a go-to for pairing with dresses.

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Pairing brown Chelsea boots with a floral maxi dress is the ultimate mix of effortless and stylish. These boots add a cool everyday vibe that tones down the floaty florals, making the outfit perfect for everything from brunch dates to weekend strolls!

Winter Dresses To Wear With Boots

When the temperature drops, nothing beats the effortless pairing of a winter dress with boots. These looks will keep you warm, comfortable, and stylish all season long.

Boots To Wear With A Maxi Dress

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Create the ultimate elevated look for all of your going out needs while keeping warm and extra stylish with this ribbed shoulder button maxi dress.

Style with our burgundy patent block heel ankle boots and a faux fur coat for a super flattering cold weather look that will have you receiving compliments all night long!

It’s always good to invest in a pair of boots that will last all year round, but most importantly look great with any outfit. Our range of boots come in standard fits and in UK sizes 7-13 to fit all of our tall women.

Shop our range of boots for tall women.

Found the perfect way to style your dress with boots? Show us over on socials using the hashtag #ImWearingLTS – you might even get featured!