Dress obsessed? Boots are a great way to fuel your obsession into the colder months. Dresses and boots are the underrated duo you can reach for whatever the occasion.
Whether you’re looking for a mini, midi or maxi dress, we’ve got the length you’re looking for and must-have wide fit boots to wear with them.
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 styles to evening-ready options, your go-to chunky boots, sock boots and lace up boots make the perfect pair.
Dresses To Wear With Flat Boots
Flat boots are the ultimate A/W staple. So, we’ve picked out our favourite dresses to wear with this versatile boot style.
Casual Dresses To Wear With Boots
Florals your fave? You’re in luck, we’ve got floral dresses for autumn/winter offering cosy long sleeves, darker prints and longer lengths.
Featuring a flattering v-neckline, long sleeves with tie detail and a casual patchwork print making it easy to style with flat boots for an everyday look.
Every wardrobe needs a basic dress to reach for on those days you want to throw something on and step out in style.
Simple in design with versatile styling options, this deep purple dress features a rounded neckline, short sleeves and two pockets! Who doesn’t love a dress with pockets right?
Black Dresses To Wear With Boots
A/W and black dresses go hand-in-hand and even more so styled with boots.
The simple 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.
This staple features a v-neckline with button detailing, long sleeves and a midi length. The midi length makes it the perfect transitional option for cooler days.
Work subtle prints into your look with ditsy florals. You’ll be reaching for this plan after plan whether it’s the office or lunch with the girls at the weekend.
Designed in a flattering milkmaid style with a square neckline and long balloon sleeves, the elasticated underbust brings shape into this floaty style. To accentuate your waist even more, simply add a black belt.
Winter Dresses To Wear With Boots
Jumper dresses are the ultimate go-to winter dress.
The shorter length of this dress makes it the perfect match for your knee high boots and ankle boots.
Designed in a relaxed, loose fit style made from a soft knitted fabric, it features a feminine v-neckline and long sleeves.
Dresses And Flat Boots Outfits
We’ve picked out our favourite dresses for flat boots, now it’s styling time!
Check out how we’re wearing these dresses with flat boots below.
Chunky Boots And Dress Outfit
We’ve added texture into this low-key dress with a longline teddy coat. Elevate it for weekend plans with chunky boots and sunnies to accessorise.
Floral Dress And Boots Outfit
We’ve kept things simple for this patterned dress to keep all eyes on the florals. For something thicker, we’ve added a longline puffer coat giving extra warmth across your legs, and classic lace up boots to complete.
Maxi Dress With Ankle Boots
Maxi dresses and ankle boots go hand-in-hand for those days you want to wear your favourite duo with extra warmth across your legs.
The check shacket takes this dress from basic to bold in an instant.
Jumper Dress And Boots Outfit
We are obsessed! This outfit is one of my favourites that I’ll definitely be recreating.
These flat knee high boots are the perfect pairing for this jumper dress keeping your outfit on point without compromising on warmth. The longline gilet gives you extra warmth across your legs too.
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.
Casual Dress To Wear With Knee High Boots
Checks are a firm favourite season after season and this A/W is no exception.
We’ve turned our midi check shirt into a dress and we’re obsessed! The belt brings definition into a relaxed style highlighting your waist.
The shorter length makes it a great option for knee high boots, with or without tights.
Going Out Dress To Wear With Knee High Boots
Effortlessly create that trending leather look for all your after-dark plans in this pinafore dress.
This chocolate brown hue is giving us all the autumn/winter vibes and we can’t get enough! Featuring a flattering v-neckline and simple strap design, the fit and flare skater skirt effortlessly sits over your curves.
Jumper Dress To Wear With Knee High Boots
Knee high boots aren’t only reserved for your shorter dresses.
This knee length dress features a simple rounded neckline, long sleeves and side splits, making it the perfect match for knee high boots.
Dresses And Knee High Boots Outfits
We’ve got our favourite dresses for knee high boots, now it’s styling time!
Check out how we style dresses with knee high boots below.
Knee High Boots And Dress Outfit
Basics need a boost? Flat knee high boots and casual plans are the ultimate match.
We’ve kept it short and sweet with a simple black dress you can layer up with tights or wear on its own. Wrap up your look with a longline cardigan to complete the look.
Blazer Dress And Boots Outfit
Heading out-out? Elevate your night out plans with heeled knee high boots.
We’ve opted for an all-black-everything look pairing these heeled knee high boots with a smart blazer dress. Whether it’s date night or drinks with the girls, this look is guaranteed to get heads turning.
Jumper Dress And Knee High Boots Outfit
Sunday lunch with the family? Keep things casual but elevated with this jumper dress and heeled knee high boots combo.
We’ve added a gilet for extra body warmth on those crisp chilly days.
Dresses To Wear With Heeled Boots
Heeled boots take your dress from day-to-night in an instant.
Elevating any casual style and polishing off any evening option, they’re the ultimate winter heel.
Midi Dress With Heeled Boots
Fuel your animal print obsession in this Limited Collection dress. The style you can dress up or down to fit any occasion, adding heeled boots gets it date night ready.
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.
Party Dresses To Wear With Boots
Party season plans? For a winter appeal, switch out your go-to strappy heels for heeled ankle boots. They still elevate your look and give extra warmth to your feet in the boot style.
Our Yours London wrap dress is the ultimate party head-turner. Designed with a floaty chiffon overlay, it features a metallic spotted pattern, flattering wrap front and long sleeves.
Dress And Heeled Boots Outfits
The dresses have been picked and now let’s add height with the heeled boots we’d wear with them!
Midi Dress And Ankle Boots Outfit
We’ve given our leopard print dress a grungy leather look feel.
Heeled knee high boots can be worn with long dress too. They not only elevate any dress but add even more warmth across your legs, what a bonus! Throw on a faux leather jacket for a look perfect for a drink (or two) at the pub.
Black Dress And Boots Outfit
This outfit shows how you can dress up a casual style as well as keeping it low-key for daytime styling. We’ve added heeled sock boots to highlight your legs and define a floaty style.
Heeled sock boots and a matching bag instantly elevate this ditsy dress and pull the look together. For evening luxe, we’ve opted for a faux fur coat.
Party Dress And Boots Outfit
Not just reserved for casual dresses, our heeled sock boots are the perfect match for your party dresses too.
The fitted style of them elongate your legs, perfect for your go-to LBD and sparkly number. We’ve added a pop of colour into the sparkles with a green shoulder bag, the colour of the moment.
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.