The Best 18 Boots to Wear With Mini, Midi and Maxi Dresses

last updated 26 October 2023

I’ve never been a trouser kind of girl—aside from having given into the easy appeal of jeans, that is. Instead, you’ll find my wardrobe is dominated by one thing: dresses.

Being curvy and petite, dresses are the item I feel most confident in, and I’ve garnered quite the collection of them over the years. However, when it comes to winter, I always find myself at a loss. During the summer months, I’ll style them with slip-on tan sandals or black minimal mules but, when the temperatures drop, I seem to struggle to find the right footwear to pair with them.

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Karina wears a printed midi and boots from Phase Eight.

Boots are, of course, essential at this time of year, but I’ve always found it difficult to decide which boot iterations look best with mini, midi and maxi dresses respectively. So, I set about rectifying that.

Having spent large amounts of time trawling through the social media ether, I can say with complete certainty that I’ve found the combinations that work best. From maxi and mini to lace-up and Western, keep scrolling to discover which boots to wear with mini, midi and maxi dresses once and for all.

DRESS TYPE: MINI

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Thanks to the space between the hem and your boots, minidresses loan themselves well to more ornate boot styles, such as lace-up fronts, as well as more directional silhouettes, including Western iterations. That said, they can look incredibly sexy worn with thigh-high boots.

1. LACE-UP

Whistles

Dahlia Lace Up Boot

These feel familiar yet fresh.

Theory

Laced Boot in Satin Leather

Take a break from your go-to black boots with burgundy or brown.

2. OVER-THE-KNEE

Reformation

Ruby Over the Knee Boot

Show off the thigh in these long and luxurious boots.

Free People

Logan Over-The-Knee Boots

With a knitted mini dress and trench coat over top? Sign me up!

3. WESTERN

Black & Camel Signature Leather Forever Comfort® Suede Western Boots

Perhaps my favourite cowboy boots on the high street right now.

M&S Collection

Leather Western Block Heel Ankle Boot

Western but wearable.

DRESS TYPE: MIDI

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Typically speaking, there are few boots that won't go with midi dresses. But, in our opinion, the strongest pairing is slouchy knee-high boots; particularly when you match them to the shade of your dress. As far as flats are concerned, a chunky moto boot will also work—the midi length will stop them from looking frumpy. If you're petite or desire a little extra height, why not consider an on-trend platform sole shoes.

1. MOTO

Jigsaw

Biker Boot in Cream

These cream boots look so premium.

Mango

Buckle Ankle Boots

These will also look great with jeans tucked in.

2. SLOUCH

Free People

First Friday Slouch Boots

I can't see this design ever going out of style.

H&M

Suede Knee-High Heeled Boots

So smart.

3. PLATFORM

Russell & Bromley

Stevie

Go full retro and add a fringed suede jacket over your dress.

Jonak

Brigand Glossy Leather Boots

The platform sole means these aren't high, but still impactful.

DRESS TYPE: MAXI

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Maxi dresses can often feel as if they're swamping you, which is why we recommend donning pointed-toe heeled boots, which will help to elongate your frame. Often floaty, we also suggest trying a white or suede style for a softer finish than typically heavy leather.

1. POINTED-TOE

John Lewis

Sugarpuff Microfibre Stretch Stiletto Heel Long Boots, Black

A classic.

& Other Stories

Pointy Sock Boots

This colour is a dream for autumn.

2. WHITE

& Other Stories

Squared Toe Leather Boots

For a white boot, these don't feel too statement.

H&M

Knee-High Heeled Boots

H&M impresses yet again.

3. SUEDE

Sézane

Gabrielle Low Boots

An everyday footwear option if ever I saw one.

The Reformation

Remington Ankle Boot

I'm fully on board with this minimalist design.

This post was originally published at an earlier time and has since been updated.

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Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.

Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.