Skip to Content

Which Dresses to Wear With Boots – Style Guide

It can be difficult to decide which dresses to wear with boots when there are so many style options out there. To help with this I have created a dresses and boots guide, to provide outfit inspiration for as many different types of boots as possible.

I wanted to cover all of the bases, so you can have a scroll through and see which types of dresses will suit the boots you are currently trying to style.

First let’s start with some quick dresses and boots outfit combinations…

Which dresses to wear with boots:

  • With ankle boots wear skater dresses and tights for a modern look.
  • With knee high boots wear fitted dresses that come to the mid-thigh for a sleek look.
  • With Chelsea boots wear minimal dresses of any length for a chic city look.
  • With heeled boots wear tailored dresses for a more elegant look.
  • With tan boots wear linen midi dresses for a trendy summer look.
  • With combat boots wear short tea-dresses and floral dresses for an in-style look.
  • With chunky boots wear floral mini dresses for a cool ’90s grunge look.

Those are just some initial ideas of what dresses work with different kind of boots for quick outfit inspiration. There are plenty more dress options for each type of boot, which I will delve into (pictures included!) below.

This post may link to online stores. If you click a link and buy something, I may get a commission. Learn more.

Pin me on Pinterest to save me for later!

what dresses to wear with boots

Chunky boots and combat boots

With combat boots for example, any kind of short, frilly tea-style dress looks great, as the two clothing items are a contrast to each other, creating a trendy style. Adding ‘tough looking’ boots to feminine dresses was a trend made popular in the ’90s by girl grunge bands as a way of blending femininity with rock and roll. This trend has stood the test of time and is still really popular today.

dresses with combat boots
Sources: Unsplash

Short feminine dresses also look great with chunky boots for the same reason. Cute floral dresses, dresses with frilled hems, Peter Pan collars or puff sleeves all work really well with these type of boots, in spring, summer autumn and winter! In the warmer months wear your chunky or combat boots with a short, light coloured tea-dress, as pictured below. In the winter months opt for a floral patterned dress that incorporates a darker colour or black so you can easily pair it with tights and chunky boots for a winter version of this pairing.

Shop this style:

Tan boots

Tan boots are an excellent option for summer, as they fit with lighter coloured clothing and are versatile when it comes to pairing them with dresses. As pictured below you can see how three different types of tan brown boots fit with three different styles of summer dresses.

Pairing the tan colour of the boots with a brown, beige or camel coloured dress is an easy way to make an outfit look put-together, by keeping the clothing in the same colour family. This look works well for any event, whether you are heading out for a picnic, picking up groceries or going out for evening drinks to a trendy bar. Matching tan boots to a tan dress creates an easy colour base that can be dressed up with accessories. Add jewellery and heavier makeup for an evening look, or keep it summery and light with a hat during the day time.

Dresses with tan boots
Source: Unsplash

Alternatively, pairing tan ankle boots with a short, patterned summer dress is a great option for a day time look (as pictured above).

If you want to dress up tan boots for a nice day time event, such as a lunch out with friends, pair the boots with a light coloured cotton or linen dress that covers the shoulders and add other tan coloured accessories. A tan belt and handbag works particularly well to tie the outfit together, as pictured above on the right.

Expensive looking lace up tanned boots are a great way to elevate a day time dress, as they add a touch of casual class to the outfit. Similarly an expensive looking tanned bag will create the same effect, and tie in the shoes nicely.

Here are some more dress and boot combinations to help inspire you further…

What dresses look good with boots?

Pair midi dresses with ankle boots for a versatile look suitable for a range of occasions. With maxi dresses avoid low heeled boots and instead opt for a higher heel, to elongate the legs and balance out the length of the dress. Chunky boots work well with short dresses for a trendy, in-style look. For a more polished look pair sleeker boots with tailored dresses.

Skater style dresses look particularly good with boots as they are a versatile pairing. The feminine, flared silhouette of a skater dress pairs well with any style of boot, to create a well put together outfit.

Here are some skater dress and boots outfit ideas that illustrate the above:

  • Wear a short sleeved floral skater dress with chunky boots for a ’90s look.
  • Wear a black strappy skater dress with knee-high or thigh-high boots for a sexy evening look.
  • Pair a dark coloured sleeved skater dress with black ankle boots and tights in winter.
  • Match a light coloured skater dress to tanned boots in the warmer months.

What dresses to wear with ankle boots?

Most kinds of dresses wear well with ankle boots as they are a versatile shoe available in a range of styles and colours. Wear tailored dresses with sleek ankle boots with a taller shaft and pair more casual dresses with chunkier ankle boots for a modern style.

Below I have styles three different kinds of dresses with black ankle boots to illustrate the above.

dresses with black heeled boots

On the left I paired a black bodycon dress with my ankle boots and a coat for a sleek winter outfit. In the middle I paired my ankle boots with a tailored red shift dress and a tweed blazer, for a business casual outfit with ankle boots.

On the right I paired a wrap dress with a black turtleneck and tights with my ankle boots as a way to transition a summer dress into the colder months.

For summer outfit options pair tan ankle boots with linen dresses, short tea-style dress and midi cotton dress for easy style combinations. Wear heeled ankle boots with maxi dresses for a boho look in summer, and pair low heeled ankle boots with above the knee dresses for a relaxed style.

For more boot outfit inspo, check out: What Jeans Do You Wear With Boots? – Ladies Guide

What dresses to wear with Dr. Martens?

Wear short floral or tea-style dresses with Dr. Martens for a trendy ’90s inspired style. Pairing the chunky Dr. Martens boot with a short feminine dress adds a touch of grungy, rock and roll juxtaposition to your outfit, for a cool and stylish twist.

Dr. Martens pair well with a range of dress styles and add a ‘tough edge’ to any outfit. Try pairing your Dr. Martens with a midi length black bodycon dress and a flannel shirt for an easy edgy look. Alternatively wear your Dr. Martens with tights and a dark coloured skater dress for a simple yet stylish outfit option.

Here are some dress outfit ideas for different Dr. Martens colours:

  • Wear white Dr. Martens with a monochrome patterned dress (e.g. hounds tooth) for a striking outfit.
  • Pair burgundy Dr. Martens with a skater dress and denim jacket for a casual outfit.
  • Style black Dr. Martens with a puff sleeved floral tea dress for an easy ’90s look.

How to wear knee-high boots with dresses?

Wear black knee-high boots with close fitting burgundy, black and grey dresses of mid-thigh length for a sleek style suitable for day or night. Pair with or without tights, depending on the occasion. This is a great style for clubbing or for an evening date.

For a fancier event, try pairing knee-high or thigh-high black boots with a black tulle or mesh babydoll dress, as pictured below on the left for a unique yet feminine outfit.

Knee high boots and dresses
Sources: Unsplash

Pair tanned knee-high boots with cream, taupe or camel coloured dresses for a classy pairing in a lighter colour family. This is a great day time look for a nice lunch out with friends or for a day time date.

With grey knee-high boots wear white, black, blush pink or grey dresses for a put-together feminine look.

A note

Thank you for reading this dresses and boots style guide and I hope you now feel confident to head to your wardrobe and try styling some outfits!

For more fashion tips, check out the below…

Related articles

What Jeans Do You Wear With Boots? – Ladies Guide

10 Ways to Style Dresses in Winter