Comfortable Shoes To Wear With a Dress

Last Updated on 2022-08-20 by Olufemi Lydia

Boots are a great way to add an extra layer of warmth and style to your outfits. They’re also a practical addition since they can help protect your legs from the elements, which is especially important during colder months.

There are a lot of different styles of boots that you can wear with dresses — you just need to find the right pair for your outfit and the occasion. Here are some of our favorites!

Chelsea Boots

Chelsea boots are ankle-length boots with laces or zippers on the side. They come in a variety of materials, including leather, suede and canvas. Chelsea boots can be worn with dresses, skirts and pants alike as long as they fit within the color/style guidelines for those articles of clothing (for example: no colorful material with black trousers). If you’re wearing one color all over or have an outfit that doesn’t have any special requirements for footwear, then these are a great option!

Comfortable Shoes To Wear With a Dress

how to wear ankle boots with dresses pictures guide

How to Wear Ankle Boots With Dresses – Pictures Guide

Many of us wonder how to wear ankle boots with dresses when planning our wardrobes for each season, or choosing a new pair of ankle boots to add to our shoe collection. It’s a common style question that can be quite tricky to answer as there are so many different styles of ankles boots and dresses that pairing them can seem overwhelming!

To help with this I have created an easy ankle boots and dresses picture style guide, to cover as many bases as possible (including casual style, office and business wear and evening wear), so you have all of the fashion tips you need to start styling your outfits.

How to wear ankle boots with dresses:

Match your ankle boots to the style of dress you will be wearing. Pair more elegant dresses with sleek, heeled ankle boots with a shaft that fits to the calf, and pair more casual dresses with flat and comfortable ankle boots for a relaxed style.

There are a few simple style rules to follow when pairing your booties to your dresses which I will break down for you, including pictures of how I style mine, below…

Seasonal style rules to follow:

  • In spring wear brown or light coloured ankle boots to match floral dresses, tea-dresses and wrap dresses for a classically feminine look.
  • In summer pair brown/tan ankle boots to midi linen dresses, mini floral dresses and patterned printed dresses for a bright and stylish look.
  • In autumn match either brown or black ankle boots with skater dresses and tights for a cosy and cute look.
  • In winter wear black ankle boots with layered dresses, long sleeved dresses and sweater dresses and black tights for a polished yet warm style.

A good rule of thumb is to pair lighter ankle boots with dresses in spring/summer, and darker ankle boots that match your tights with dresses in autumn and winter. If you keep those colour rules in mind it will be much easier to make an outfit look put-together.

Of course these fashion ‘rules’ are subjective, and more like ‘traditional guidelines’ for styling clothes – you don’t have to follow them exactly if you don’t want to!

Ankle boots and dresses style guide

Here is how I style different kinds and colours of ankle boots, with pictures for you to refer to…

Black ankle boots

dresses with black ankle boots

Black ankle boots are super versatile and match many different styles of dresses. They look great with tights in the cooler months and can create the illusion of longer legs. I find black ankle boots that are fitted to the calves look best, and they work well for business casual office wear too.

In the above picture I paired my black ankle boots with three different kinds of dresses that are suitable for the autumn and winter months, to show how easily the boots match to all. The boots wear well with a velvet dress, a fitted dress and a floral dress – wow!

Brown ankle boots

Dresses with tan boots
Sources: Unsplash

Brown ankle boots are a summer staple in my opinion, as they match so well with all kinds of summer dresses. Chunky brown ankle boots, suede brown ankle boots and lace up brown ankle boots all work well to dress up a summer dress – definitely a versatile purchase!

In the above picture you can see how they pair nicely with a floral mini dress, a midi linen dress and an knee-length tailored cotton dress, for a light and bright look.

Heeled ankle boots

dresses with black heeled boots

Heeled ankle boots pair well with more elegant or professional looking dresses, to give your outfit an edge of trendy sophistication. I find darker heeled ankle boots for well with these kinds of dresses, and they also match easily to tights for a winter look.

Flat ankle boots

Flat ankle boots match nicely to more casual dresses, such as a skater dress, t-shirt dress or a comfy sweater dress. Flat ankle boots make for the most comfortable ankle boots, and are perfect for day-to-day wear. They suit everyone and can look really stylish.

The Chelsea boot is a great example of how trendy a flat ankle boot can be, as it’s favoured by celebrities for a laid back, city style.

My top pick – this Chelsea boot by Clarks is comfortable, good quality and super on-trend:

Clarks Women’s Taylor Shine Chelsea Boots

Now we’ve got the basics covered, let’s get into some frequently asked style questions…

Do ankle boots go with dresses?

Ankle boots go well with dresses, when the right styles are paired together. For more elegant dresses wear sleek heeled ankle boots that fit to the calf and for casual dresses wear flat and comfortable ankle boots. In summer choose brown ankle boots over black to match lighter dresses, and vice versa in the winter.

Ankle boots look great with dresses of all kinds, as there are so many styles available of this versatile shoe.

Best ankle boots for dresses

The best ankle boots for dresses are chunky, brown ankle boots for casual/summer dresses and black, sleek ankle boots for more elegant dresses. For more formal dresses opt for a heeled ankle boot with a tall shaft that fits to the calf, for a polished look.

Different ankle boots go with different styles of dresses, so you need to match up your garments before stepping out. Here are some tips for shopping the best ankle boots for dresses…

Best brown ankle boots for dresses

The best style of brown ankle boot in my opinion is a versatile chunky boot with a low comfortable heel, as it’s likely you will be pairing this boot with casual outfits and dresses. Staying comfortable and being able to walk distances is essential for casual boots.

This pair of brown ankle boots fit the bill, as they are trendy yet comfortable, for day-to-day wear:

Lotus Tan Leather Lucinda Ankle Boots for Women

They would pair well with lighter coloured dresses and transition easily between the seasons.

Best black ankle boots for dresses

The best style of black ankle boots are heeled and sleek, with a tall shaft that fits to the calf. This style is more elegant, and can be paired with dressier dresses on the weekends, and business casual dresses for the office. They also look amazing with jeans.

This pair of black ankle boots is particularly gorgeous (the pointed toe is so chic), and would style well with many dresses:

C.PARAVANO Ankle Boot

They would pair well with business casual dresses for the office or with trendy dresses for a night out at a bar or romantic dinner. They would also look great over black tights in the winter, to elongate the legs.

Are ankle boots still in style?

Ankle boots are still in style in 2021 and 2022, as they continue to be a versatile and well loved style of shoe. Black heeled ankle boots that are fitted to the calves are particularly modern. Wear with a floral tea-dress for a cool and trendy look.

There are so many styles of ankle boots that it’s hard to imagine they will ever go out of fashion. They suit everyone, of all ages and are versatile for day and night wear, office wear and for running errands.

The most stylish ankle boots for day wear are more casual, and pair well with both summer and winter dresses. A brown or black low heeled chunky ankle boot looks great with day wear and matches almost every kind of day dress.

The best ankle boots for evening wear are darker in colour and more sleek in design. Go for a higher heel and match them to elegant or trendy dresses for a night out with the girls or for a date.

Chelsea ankle boots also pair well with many kinds of dresses for a modern twist.

A note

Thank you for reading this ‘ankle boots and dresses’ guide – I hope you now feel inspired to grab a pair of ankle boots if you don’t already own some, and pair them with your dresses!

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