Dresses and boots are the underrated duo you can reach for whatever the occasion. Fuelling your obsession into the colder months whether you’re looking for a mini, midi or maxi length.
Ready to take your style from last season to hot right now? Check out our ultimate guide below.
Best Dresses To Wear With Boots
We’ve made finding the best plus size dresses to wear with boots easy.
From everyday casual dresses to evening-ready silhouettes, your go-to chunky boots, sock boots and lace up boots make the perfect pairing.
Dresses To Wear With Flat Boots
Flat boots are the ultimate day-to-day staple. We’ve picked out our favourite dresses to wear with this versatile boot style.
Casual Dresses To Wear With Boots
Collared dresses are our go-to throw on dress style for those days we want to wear something cute but comfortable.
The loose floaty style is super comfortable for all day wear. Made from a soft fabric featuring a smart casual collared neck and long sleeves. The two side splits add dimension into a loose style or pop a belt on to define your waist.
We love how versatile this dress is for wearing with tights and boots on colder days and bare legs when the temperature warms up.
Made from a knitted jersey fabric, it features a simple rounded neck, long balloon sleeves and sits at knee length.
Every wardrobe needs a basic dress to reach for on those days you want to throw something on and step out in style.
For a lighter option you can layer up or wear on its own, our best selling drape pocket dress will be your new go-to. The simple design makes it a great option to style up or down.
Made from a comfortable ribbed stretch jersey fabric, it features a simple scoop neck, 3/4 length sleeves and two front drape pockets in a floaty swing style.
Animal print your go-to? You’re in luck, they’re the perfect match for your favourite chunky boots too.
Featuring a flattering v-neckline, 3/4 length flute sleeves and a midi length hem makes it easy to style with flat boots for an everyday look.
The print will see you throughout this season and the next in style.
Black Dresses To Wear With Boots
A/W and black dresses go hand-in-hand and even more so styled with boots.
The mono hue means you can slip on a range of boots from classic lace ups to buckle detailing and patterned boots – the options are endless.
Work a print into your black dress collection with this easy wearing floral maxi dress.
Comfortable in a jersey fabric with an all over ditsy floral print, it features a simple v-neckline, long sleeves and pleat detail to the bust.
The faux leather jacket adds texture and elevates the dress for a grungy after-dark look. We’ve added a belt to dress it up and cinch in your waist or you can leave it loose and floaty.
Hoodie dresses give an effortless athleisure luxe look.
Made from a comfortable jersey fabric, it features a notch neck with embellished detail, long sleeves and a large front pocket.
We love how it looks with tights and boots for a layered up look and take it into spring with chunky trainers.
Dresses To Wear With Heeled Boots
Heeled boots take your dress from day-to-night in an instant.
Elevating casual styles and polishing off any evening option, they give your after-dark plans to new heights.
Plus Size Dresses To Wear With Cowboy Boots
Cowboy boots are the new must-have style to step into. We’re seeing the western-inspired boot all over our Insta feeds and we’re obsessed.
Be the best dressed and tap into the latest trends with stripes and cowboy boots – this look really has it all.
Exclusive to our Yours Luxury range, this striped jumper dress features a quarter zip fastening, long sleeves and split hem detail.
The long length and knitted fabric means you can get away with braving bare legs, and we love how they show off the top of the boots too.
Our brown cowboy boots are the perfect way to lighten up any dress for a spring feel that keeps you warm. We love how they complement this blue smock dress effortlessly.
Made from a comfortable stretch jersey ribbed fabric, it features a simple rounded neck, long sleeves and tiered smock hem.
Take this look to your next day date wearing a brown shoulder bag and accessories.
Dresses To Wear With Heeled Ankle Boots
Your favourite floor sweeping styles are the perfect match for heeled ankle boots. Offering extra warmth with the longer length, ankle boots sit seamlessly underneath your dress.
This timeless polka dot print is forever flattering and always on trend, featuring a keyhole tie neckline, long sleeves and floaty loose fit.
Dresses Wear With Knee High Boots
Knee high boots elevate any outfit and add extra warmth across your legs too. From short to long dresses, knee high boots let your legs do the talking whatever the occasion.
Checks are a firm favourite season after season.
We’ve turned our midi check shirt into a dress and we’re obsessed! The belt brings shape back into a relaxed style highlighting your waist.
The shorter length makes it a great option for flat knee high boots, with or without tights.
Jumper dresses and knee high boots go hand-in-hand for keeping your outfit on point without compromising on warmth.
Made from a soft knitted fabric in a loose fitting style, it features a deep v-neckline and long sleeves.
We’d take this look to a pub lunch or shopping trip with the girls.
Knee high boots are perfect for your longer dresses too and they add even more warmth across your legs, what a bonus!
If you’re looking for a smarter evening option this shirt dress ticks all the boxes. It features a button through fastening, collared neckline and 3/4 length sleeves. We’ve added heeled knee high boots to elevate the dress for a date night look you’ll love.
Shop Plus Size Dresses in UK sizes 14-40 for more must-have styles.
Best Boots To Wear With Dresses
Need to refresh your boots collection? We’ve got you.
Check out our favourite boots to wear with dresses below.
Knee High Boots
Shop Wide Fit Boots for more must-have styles in UK sizes 3-10.
Show us the dresses you’re wearing with boots over on social using the hashtag #ThisIsYours on Instagram, Facebook & Twitter – you might even get featured.