The best boots to wear with dresses are a wardrobe essential, as soon as the temperature drops. But with so many different styles of boots and lengths of dresses available, it can be difficult to know which style goes with what. Pick correctly though, and the right pair of boots can transform an outfit, taking you from cosy pub lunches to more formal festive occasions.
Working out the best boots to wear with dresses depends on a few key things. The first thing to establish, when looking for the best new-in boots this season to wear with dresses is the length of dress you want to wear them with. Then establish the occasions you might want your boots and dress combo for and finally, don't forget, your personal aesthetic plays a role here too.
While some boot and dress combinations are considered a classic - knee-high boots and mini dresses, anyone? - there are other more unexpected combinations that you may not have considered, that play into the latest boot trends 2023, such as integrating chunky soled designs, or Western-inspired boots into your everyday looks. One thing is for certain though, the boots and dress combo is one that is here to stay.
The best boots to wear with dresses according to a fashion editor
Ultimately, deciding on the best boots to wear with dresses depends a lot on your own personal style. Those with a penchant for rock chick chic, will instantly be drawn to biker boots and a mini dress, while those carefully curating a boho capsule wardrobe may favour a cowboy boot/midi dress ensemble.
With so many possibilities at your disposal, don't be afraid to experiment. Think about the hemline of your dress will interact with the top of your boot and consider ways to lengthen your legs, by cutting it in the least amount of places, or at least having a good amount of distance between the dress hem and boot top.
1. How to wear cowboy boots with dresses
While you’re more likely to reach for your jeans to pair with your cowboy boots, don’t dismiss your favourite dress as a perfect fashion partner says celebrity stylist Miranda Holder.
“Cowboy boots lend a carefree vibe to a look and are a firm favourite for festivals adding instant cool to any dress,” she says.
As cowboy boots are generally more casual, Miranda says it’s best to team them with a similarly relaxed style of dress. While length isn’t too important, a more boho style dress is a great partner to the cowboy boot.
Miranda adds: “The aesthetic is free-spirited, and you are aiming for anything floaty, with ruffles or with voluminous sleeves. Any length is fine - think channelling your inner hippy whereby natural fabrics work best.”
While denim is always a natural partner for the best cowboy boots, don’t discount more extreme styles of dress either – sequins, tulle, and leather all work well with this type of boot.
“The rule here is definitely more is more, and somehow the cowboy boots seem to bring it all together,” advises Miranda.
Miranda Holder is an acclaimed fashion stylist and expert who studied fashion at Central Saint Martin’s and whose portfolio proudly showcases a variety of high-profile names in entertainment, from number-one girl band Little Mix to Boy George and Hollywood actress Vanessa Williams. Miranda is also a regular media commentator and TV fashion expert on QVC, and lecturer at London College of Fashion.
RRP: £65 | Don’t leave pretty floral prints to the warmer months – they work just as well in a winter capsule wardrobe, especially when teamed with boots and a cosy knit. The floaty silhouette will skim your shape, while the empire line creates a flattering and defined bust line. Add heels for a winter wedding look.
£125 | If going full-on Western isn’t your bag, choose a pair of cowboy boots that have a nod to the aesthetic without being too Dolly Parton. Cream boots have been in the spotlight for a couple of years now and add a modern touch to any boot outfit, while the 6.5cm heel gives some height without sacrificing on comfort.
RRP: £59.90 | Want to get maximum wear out of your summer dresses? A sheepskin jacket is the way to go. Throw a snuggly piece of outerwear over any dress to make it winter appropriate. One of the best winter coats, opt for a design in cream and beige tones as it will look look less severe against lighter pastel shades.
2. How to wear biker boots with dresses
Back on the fashion radar this year as part of the latest autumn/winter shoe trends 2023, the biker boot is one of the best black boots you can have in your shoe capsule wardrobe, as they’re incredibly versatile.
“You can’t go wrong with a biker boot,” says Laura Schofield, founder of shoe brand for ladies with larger feet, Otto + Ivy.
“They look amazing with midis, minidress-and-tights-combos… the lot.”
When it comes to wearing biker boots with dresses, it’s all about mastering the art of contrast. The rebellious essence of biker boots juxtaposed against the femininity of dresses creating a truly stylish fashion statement.
“Anything that feels a bit overly ladylike or stuffy can be given a little bit of an edge with a biker boot,” says Laura. “I’ve even been known to rock them with a biker jacket and ballgown.”
If you don’t have a ball gown to hand, biker boots add a rock chick feel to mini dresses in leather or a pretty cocktail dress. They also look great for more dressed down days, teamed with a jumper dress.
Former shopping television presenter, Laura Schofield, launched Otto + Ivy after struggling to find stylish footwear for her size 9 feet. Otto + Ivy shoes aren't simply small shoes made bigger; they are exclusively designed to flatter a long foot and are engineered to support the physique of a tall woman. Now her shoes are worn by women all over the world. The brand is a firm favourite of celebrities with bigger feet including Alison Hammond, Caitlyn Jenner, Sara Davies, Angela Griffin and Caroline Hirons.
RRP: £26.99 | A metallic dress is always a great wardrobe staple and perfect for all those party invites, especially come Christmas time. The square neck and puff sleeves on this one is super flattering, while the tie belt will help create a waist.
RRP: £249.99 | Made in Portugal from butter soft leather, these biker boots are timeless. Not only do they look good, but thanks to the ‘Loving Air’ foot bed, they also feel great underfoot. Perfect for all day events when you need style and comfort.
RRP: £39.99 | Biker jackets are an essential for any minimalist capsule wardrobe as they go with everything. Chucking one over a pretty dress is a great way to add some edge to a party look, offering a more laidback spin to proceedings.
3. How to wear over the knee boots with dresses
“Over the knee boots are hot this season!” says Miranda. “They are slinky and seductive and make a statement all of their own."
She continues: “Classic, slouchy knit dresses are a match made in heaven for an over the knee boot, giving a relaxed but sophisticated aesthetic.”
Choose a dress in the colour of the season for an easy way to wear red, or go for more neutral shades teamed with soft suede boots for a look that’s both cosy and sensual. Going for a shorter dress hemline allows the boots to take centre stage. Miranda advises adding cycling shorts underneath your dress if you’re worried about your modesty.
If you’d rather go for a longer length dress, try one that has a split up it so you can still show off the effect of the thigh high boots.
Alternatively, wear over the knee boots with a pair of dense or leather leggings, or your best skinny jeans. This is a leg-lengthening styles that still feels covered.
RRP: £55 | White knitwear for winter exudes Quiet Luxury, and this affordable Quiet Luxury piece is kind on your bank balance too. Wear with the belt for a fitted '60s-inspired feel or wear loose for a more casual look. You can also swap the belt for a leather design for a little more styled polish.
RRP: £165 | Slouchy thigh high boots are one of the big autumn/winter fashion trends for 2023 and they’re an easy way to update your favourite dresses. The block heel means they give you all the height without making it tricky to strut your stuff.
RRP: £21.99 | Warm up your winter looks with a furry bag, one of the big autumn/winter handbag trends for 2023. If you don’t want to invest heavily, this one from H&M is perfect. It’s snuggly, ideal for every day, and it won’t break the bank.
4. How to wear knee high boots with dresses
A classic for a reason, knee high boots, are not only versatile but can also be dressed up or down, depending on the occasion. They will literally go with any length of dress in your wardrobe, from mini to midi.
“I love a knee-high boot with a pretty printed midi dress, layered up with a gilet or shearling jacket,” says Laura.
And while knee high boots can be styled with any dress, you should still pay attention to the proportions. If you go for a chunkier knee high boot, perhaps choose a slightly fuller or A-line dress, while a slim pair of knee high boots will work well with a more fitted style of dress.
They’re also a fabulously practical boot for the colder months, keeping those calves warm. Match your boots to the colour of your dress for immediate leg-lengthening properties. Or create a brown boots outfit, with other neutral or autumnal colourways for a cosy feel.
Leather will give a more polished finished to your look, while suede creates a softer feel, but will need extra protection from wet and damp weather.
RRP: £69 | The best midi dress, like this one, can be dressed up or down, going from the office to the evening with ease. The open back gives it a sensual feeling, but equally, throw on a chunky knit and some boots and you’ll be ready to go for a more casual outing.
RRP: £180 | If you’re going to splash the cash on a pair of knee high boots, these are the ones. The classic design won’t date, they’re leather and the block heel means they’re easy to walk in while giving you that extra height. Timeless, they deserve a spot in your autumn capsule wardrobe.
RRP: £62 | A furry gilet is a fantastic investment thanks to its versatility and warmth. One of the many types of coats worth investing in, this borg gilet will work from autumn through to your early spring capsule wardrobe. Ideal for what to wear over a dress, you can also team it with jeans.
5. How to wear chunky boots with dresses
In recent times, chunky boots - whether platform heels or rugged lug soles - have become popular in fashion. These boots are both stylish and practical, making them a great choice to complete your outfit.
“Chunky boots give a bit of hipster-cool edge to all sorts of dresses, converting prettier pieces into more appropriate daywear,” says Miranda.
“They go with everything from tea dresses to bodycon jersey frocks to more structured pieces.”
Chunky boots come in all shapes of sizes from classic DMs to flatform Chelsea boots. When it comes to choosing the right dress then, opt for styles that complement the chunky boots' boldness.
Shorter dresses are a failsafe with chunky ankle boots - the contrast between the hemline and the boots gives off a youthful, rebellious vibe, something many of us wouldn’t mind tapping into - for extra coverage, just pair with opaque tights. Knee high chunky soled boots also work well with this dress length but keep to ankle height if you’re choosing a midi or maxi dress.
RRP: £75 | The denim dress gets a new season makeover. Part of Nobody’s Child collaboration with presenter Fearne Cotton, the puff sleeves and zip on this dress give it the flexibility to be dressed up or down and with adjustable levels of cleavage too.
RRP: £59.99 | If you want to spice up your boot wardrobe this winter, go for cream. As a neutral, they're just as versatile as black, but they can add a touch of lightness in darker months. Team these with everything from dresses and jeans to leather look leggings.
RRP: £89 | An oversized coat is a great winter buy. You can throw it over the chunkiest of knits without feeling constricted and it also smartens up any casual outfit. As the winter months can be a bit gloomy, we say tap into the coat trends 2023 with this big and bold design.
View the latest John Lewis discount codes from woman&home's voucher team to get money off your next purchase.
6. How to wear metallic boots with dresses
Silver and gold have been on the trend radar for a while now, whether it’s metallic trousers or glittering footwear. While you might think that metallics only work for a party shoe, don’t dismiss a shiny boot.
“A metallic boot is actually incredibly versatile,” says Laura.
“They look great styled with neon brights and bold patterns, but are equally useful when you’re struggling to make an all-black outfit look a bit more fun.”
These are boots that you want to show off, so a mini dress is a great choice. And as Laura suggests, don’t be afraid of adding some colour. Many of the fashion colour trends for 2023 – such as red and icy blue – work really well with silver and gold.
If you’re more of a minimalist dresser, don’t be put off by a pair of glittering boots. Keep the rest of your outfit simple and understated – perhaps a navy or black midi dress - as this will ensure that the boots are the statement piece, but without being too over the top.
RRP: £32 | Sheer is one of the big autumn winter dress trends for 2023 and a dress like this one will see you through parties, meet ups with friends, date nights and even answering what to wear on Christmas day with just a few different accessories.
RRP: £139 | These boots are definitely made for walking – and strutting and posing. If you have size 8 feet or over, it can be hard finding stylish shoes and boots, but that’s where Otto + Ivy come in, creating on trend footwear that you’ll reach for time and time again.
RRP: £24.04 | A detachable collar is an easy way to change the look of your favourite top or dress. Add this one to a black dress for one of autumn’s biggest trends – gothic glamour and give a plain black dress or sweater a more party-ready feel.
7. How wear pointed heeled boots with dresses
While boots are perfect for dressing down your favourite gowns, if you choose wisely, they can also be great for more formal occasions.
“You can wear boots with a dress to an office environment, or even to a fabulous ‘evening do’ if the boots ‘fit’ the occasion,” advises Miranda.
“A pointed toe and a heel help to elevate the look, and you’ll also need to keep the rest of your accessories equally glamorous.”
Miranda advises choosing polished leather over suede for an evening look, but she also says that boots that have a little sparkle on them, will also help to up the evening glamour.
As to whether you choose ankle boots or knee high boots all very much depends on the style of dress you’re wearing – and also the occasion you’re going to. An ankle boot looks sharp with a shirt dress for the office, while a polished knee high boot can take you easily into the evening when teamed with a party dress.
RRP: £120 | If you’re in an office environment, a shirt dress is the perfect buy, giving you a formal look without the need for a suit. This glorious stripey dress, is one of the best Boden autumn buys, and offers a modern take on pinstripe.
RRP: £79 | While you might be tempted to always reach for black ankle boots, but navy makes a nice change. Just as versatile, even navy and black is a stylish combo, and they look particularly great teamed with denim. This vegan-friendly pair are a great choice to wear with more feminine dresses.
RRP: £29.96 | A dupe of the influencer-friendly Bottega Veneta teardrop earrings, these statement lovelies come at a fraction of the price of the originals, but still deliver on the jewellery trends 2023. Choose from silver or gold for an easy way to add a touch of glam to any outfit.
Is it ok to wear ankle boots with dresses?
"One of the trickier boot silhouettes to pull off with a dress, you can wear ankle boots with dresses, just pay attention to proportions. Perhaps one of the biggest issues when it comes to wearing ankle boots with dresses, is that there is slight variation on what boots might be considered ankle length, with some slightly longer or shorter than others," explains woman&home fashion editor, Rivkie Baum.
"Think about the distance between the hem of your dress and the top of your ankle boot. Ideally a slightly longer ankle boot works best with all lengths of dresses. Alternatively, wear a pair of block coloured, opaque tights in the same hue as your ankle boots. This stops the boot from truly cutting at your ankle and gives the optical illusion of a longer panel of colour and lengthens your legs. This will allow you to wear any length of dress with your ankle boots."
With over fifteen years' experience, Rivkie is an accomplished fashion editor, writer and stylist. Covering international fashion weeks, and styling photoshoots all over the world, Rivkie loves translating the trends in an accessible way to make fashion available for all budgets.
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