How to Wear Chelsea Boots

by Charlotte Davies
Stylish woman wearing black chelsea boots

Many great things have come out of Chelsea: the Chelsea Art School, the Chelsea Bun, Made In Chelsea’s Mark Francis… But all pale in comparison to the Chelsea boot. Once a staple of a Victorian gentleman’s wardrobe, these beloved classic ankle boots are now iconic women’s footwear. To help you stave off any footwear faux pas, here’s our guide on how to style Chelsea boots.

Shop The Look

[show_shopthepost_widget id=”2441396″]


Top 15 Chelsea Boots

We’ve scoured the stores and searched the internet to find our top 15 Chelsea boots – from tan Chelsea boots, to coloured Chelsea boots, to classic black Chelsea boots for women.

Black Chelsea Boots

                                Dune Peppys, £95                                                                         Zara Flat Sock Boots, £29.99                                   Topshop Kiki Chelsea Boots, £42

Black and Brown Chelsea Boots

   Russell&Bromley Cavendish Chelsea Boots, £255                             ASOS Rasconi Pointed Chelsea Boots, £35                         New Look Tan Chelsea Boots, £27.99

Brown Chelsea Boots

              Barbour Ellie Low Chelsea Boot, £130                             New Look Tan Chelsea Boots, £22.99                  Giuseppe Zanotti Suede Ankle Boots, £243

Heeled Chelsea Boots

     Carvela Kurt Geiger Stacey Boots, £165                          Zara Embroidered Detail Boots, £79.99                   New Look Tan Suedette Chelsea Boots, £29.99

Patterned Chelsea Boots

                 Topshop Bumble Boots, £42                                                         Zara Two-Tone Braided Boots, £59.99                          Topshop Blossom Embroided Boots, £42

How to Wear Chelsea Boots with Skinny Jeans

Fortunately for you, choosing skinny jeans over bootleg or straight cut denim means you’re already half way there in terms of sussing out how to style Chelsea boots. Skinny jeans are undoubtedly the easiest style of jeans to pair with Chelsea ankle boots because they fit close to your foot and can easily be tucked into the top of the boot – important because you don’t want a lot of excess jean awkwardly bulging out over the top. Nor do you want to lose the opportunity to show off your excellent choice of footwear by covering most of the boot with denim.

When choosing skinny jeans to go with your Chelsea boots, it’s always important to get the length right. Just as you don’t want excess jeans hiding your shoes, you don’t want an odd strip of exposed ankle where your jeans end and your boots start either. Lots of brands now make jeans with extra long or shorter legs.

Chelsea Boots Styled for the Day

Now that you know how to wear Chelsea boots with jeans, here’s how to style the rest of your outfit.

Depending on what your plans are, there are multiple ways to work your Chelsea boots outfit. Worn with a pair of dark blue or black jeans and a sophisticated top or jumper in a soft tone, black or dark brown Chelsea boots with a heel will create a sophisticated look, perfect for lunch with the ladies. Pair with a lux-looking leather jacket and handbag in a matching brown to complete the look.

In contrast, low heeled tan Chelsea boots are a classic choice for a casual weekend wardrobe. The versatile colour means you can easily pair them with any wash of blue or black jeans and, as they are thin, they look great with easy-to-wear oversized tops and jumpers.

Stepping away from the traditional option, coloured or patterned suede Chelsea boots will also help you achieve a downtime day look.

Celebrities in Chelsea Boots

Kate Moss, Sienna Miller and Fearne Cotton demonstrate how to wear Chelsea boots during the day

Photo Credit: Pinterest

Shop The Look

[show_shopthepost_widget id=”2441432″]


Chelsea Boots Styled for the Night

The beauty of Chelsea ankle boots is that they are very versatile and will easily translate from day to night. One of the perks of Chelsea boots over court shoes or other heeled work shoes is that Chelsea boots have reasonably thick heels that are easy to walk in for long periods of time. Choose the heel height to suit how active your job is and how comfortable you are; whatever you might have thought at 17, there’s no point suffering for fashion.

When styled correctly they can look really sharp, perfect for a formal setting like the office, and later made to look very sleek, sexy and stylish for a night on the town. A pair of simple, black leather Chelsea boots with a heel are a great investment as you will be able to wear them to work with black jeans and an effortlessly elegant white silk or chiffon shirt, and then, with a quick swap of a top, out to a bar or restaurant with something a little more sexy or sparkly for a little added glamour.

How to Wear Chelsea Boots with Dresses

How to Dress Chelsea Boots: Summer

Tan Chelsea boots are the perfect staple shoes for a laid-back summer wardrobe; not only will the boots fade beautifully as the summer progresses, but also the understated colour will go with lots of brightly coloured casual dresses.

Summer is the ideal time to wear suede Chelsea boots: not only does the good weather mean the fabric will last longer, but also the relaxed fabric gives a laid back look for picnics in parks and weekend drinks by a river. Another added bonus is that the soft material is less likely to rub or cause blisters than leather boots; this is important to consider, given that you may not want to wear socks or tights in the summer heat.

As ever, the versatility of these boots mean they will go with almost every style of summer dress – from flowy summer frocks to A-line denim dresses. Chelsea ankle boots look cute with shorter, above the knee dresses and bare legs in summer. The thin boot, paired with a shorter skirt, will make your legs look longer, and, if you get a pair with a gap between the fabric and your ankle, thinner too.

Celebrities in Chelsea Boots and Summer Dresses

Alexa Chung wearing a variety of Chelsea boots

Photo Credit: Pinterest

Shop The Look

[show_shopthepost_widget id=”2441448″]


How to Dress Chelsea Boots: Winter

You can still wear Chelsea ankle boots with dresses in the winter; just add a pair of (thick) black tights. If you get chilly toes, you can also add a pair a socks on top of your tights – either discreet trainer socks or a pair of coloured ankle socks that poke out above the top of the boot, bringing a pop of vibrancy to a dark outfit. As always, though, don’t colour clash.

Winter doesn’t have to mean an absence of colour. Burgundy Chelsea boots will give a warm burst of colour to brighten your wardrobe. Plus, as burgundy is a very fashionable colour, you’ll have no problem finding a pair you like.

While a coloured dress will suit black boots, burgundy Chelsea boots will look great with a long black dress. Like burgundy, dark brown Chelsea boots will add a touch of warmth to an outfit and it’s a reasonably versatile colour to style; though everything goes with black.

Celebrity Inspiration: Alexa Chung

Alexa Chung rides bike wearing burgundy Chelsea boots

Photo Credit: Pinterest

Shop The Look

[show_shopthepost_widget id=”2441464″]


Chelsea Boots and Winter Dresses

Mid-length dresses look really chic with heeled Chelsea boots. This length is great for winter, for so many reasons; the fact it covers more skin is good for staying warm and hiding any excess Christmas weight you’re still trying to shake (don’t worry, we’ve all been there).

Both form-fitting and loose dresses go with these shoes. A simple, figure-hugging jersey dress has a street vibe which, when combined with black leather Chelsea boots, will create a fashionable look. Alternatively, finish your outfit with a pair of bright or patterned boots to put your individual stamp on the look.

The British winter normally means of a lot of rain: leather boots will stand the rain best though, for the sake of your shoes, get a strong and effective waterproofing spray.

Celebrities in Chelsea boots and winter dresses: Alexa Chung, Emma Roberts, Kate Bosworth

Photo Credit: Pinterest

Shop The Look

[show_shopthepost_widget id=”2441471″]


Styling Chelsea Boots: Top Tip

What are Chelsea Boots?

Chelsea boots closely resemble short riding boots. Traditionally they were (and often still are) slim toed, close fitting, leather ankle-length boots with a small heel, elasticated side panel, and small toggle at the back of the boot to help you slide your foot in and out.

Nowadays, Chelsea boots come in different shapes, sizes and materials. No longer confined to strict Victorian dress regulations, the height of the ankle now varies, they come in a multitude of fabrics, and the heel of women’s Chelsea boots has got higher and higher.

Celebrities in Chelsea Boots: Kylie Jenner, Rosie Fortescue, Amber Valletta

Photo Credit: Pinterest

Shop The Look

[show_shopthepost_widget id=”2441415″]


  • Keep it chic but simple by pairing your Chelsea boots with jeans. Just remember to tuck your skinnies into the top of your boots
  • For versatility, choose a pair of black Chelsea boots or tan Chelsea boots: they go with everything.
  • Add a heel to take your your boots from day to night.
  • Almost all dresses go with Chelsea boots. Choose one to suit your figure and personal style.
  • It’s really easy to find lux-looking cheap Chelsea boots. They don’t have to break the bank.

Now that you’ve figured out how to style Chelsea boots, you should be ready to put your best boot forward and confidently walk the royal borough’s most fashionable streets in style.

Read more great articles on women’s fashion here at

You may also like