As a fashion editor, these are the 6 best boots to wear with dresses this season that I'm recommending to everyone

Ready to step up your style? These are the best boots to wear with dresses this season and beyond.

Best boots to wear with dresses
(Image credit: Getty Images)

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

Three images of women wearing cowboy boots

(Image credit: Getty Images)

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.

Mirander Holder
Miranda Holder

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. 

2. How to wear biker boots with dresses

Three women wearing best biker boots and dresses

(Image credit: Getty Images)

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.

Laura Schofield
Laura Schofield

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. 

3. How to wear over the knee boots with dresses

Three women wearing over the knee boots and dresses

(Image credit: Getty Images)

“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.

4. How to wear knee high boots with dresses

Three women wearing knee high boots and dresses

(Image credit: Getty Images)

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.

5. How to wear chunky boots with dresses

Three women wearing chunky boots and dresses

(Image credit: Getty Images)

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.

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

Three women wearing gold and silver boots with dresses

(Image credit: Getty Images)

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.

7. How wear pointed heeled boots with dresses

Three women wearing pointy boots with formal dresses

(Image credit: Getty Images)

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.

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."

Rivkie Baum
Rivkie Baum

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. 

Jayne Cherrington-Cook

With over 22 years’ experience in journalism, Jayne has written about a variety of subjects. She spent the start of her career within the world of film, interviewing Hollywood stars, attending premieres and lusting after red carpet outfits, and then moved into fashion, launching websites for big magazines such as Look, Woman’s Own and Wedding and working with top fashion brands such as Westfield, LK Bennett and Hunter. 

Career highlights include dressing up as Kylie (in gold hot pants!) for a national newspaper and working on big fashion events alongside Giles Deacon, Henry Holland and Naomi Campbell.