How To Wear Chelsea Boots (9 Suggestions For Women)

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Chelsea boots are a popular and enduring wardrobe staple for both men and women. Patented in 1851 by J. Sparkes Hall, Chelsea boots are typically ankle height, low heeled, have a pointed toe, have elastic panels in the sides, and have a loop on the back for easy pull on and take off. So, how do you style an outfit around Chelsea boots? We’ve scoured the internet for the best fashion ideas for women to pull off this look.

The classic Chelsea boot style has been loved for decades for its versatility and variety – casual, formal, rugged, chic…there are many ways to wear a Chelsea boot.

  • Dress It Up – with patent leather, feminine skirts, or pretty tights
  • Dress It Down – with suede, denim, or Boho elements
  • Make a statement – with bold & bright colors, textures, or proportions

So, if you’ve finally found that perfect pair of Chelsea boots but need some inspiration on how to wear them, keep reading for nine awesome style ideas!

Woman in red pants wearing shiny brown leather Chelsea boots, How To Wear Chelsea Boots (9 Suggestions For Women)

How To Wear Chelsea Boots

Originally known as “paddock boots,” their popularity was given a huge boost by Queen Victoria, who reportedly wore them while walking and horse riding. People loved their easy-on/easy-off elastic feature, which had only recently been made possible by the invention of galvanized rubber. The style became known as Chelsea boots in the mid-1950s due to being worn by members of the mod subculture (AKA “The Chelsea set” or “beatniks”), which was based in Chelsea, London. Today, Chelsea boots can be worn to coordinate a casual look or dress to impress.

Should Chelsea Boots Be Tight Or Loose?

When you’re shopping for a new pair of boots, getting the best fit is always important. When buying Chelsea style boots, it’s best to have a snug fit, especially around the ankle and heel area. The boots should not be too loose, or your feet may slide around inside or even slip out of the boot, which is bad for both foot health and safety! There should be no gap between the boot and your ankle; the elastic sides are meant to provide that snug fit. Conversely, the boots should not be so tight that they cut off your circulation, hurt your feet, or cause blisters.

Please also read, “Is Your Boot Size The Same As Your Shoe Size?

Dress Up Chelsea Boots

A sleek, chic pair of Chelsea boots can really finish off a look. If you want to add some flair to a casual outfit, try wearing a pair of shiny patent leather or metallic Chelsea boots. This look pairs some sleek boots with dark skinny jeans, a denim jacket, and a trench hat. Great for a chill date night or hanging out with a group of friends!

Click here to see U-lite Women’s Leather Chelsea Boots at Amazon.

Want to smarten up a pretty, feminine skirt or dress? Try wearing it with a sleek, shiny pair of Chelsea boots. Add a crisp, short jacket and tights on colder days. Here’s a great look for the office or a professional meeting – a monochromatic palette with a leather miniskirt and fuzzy jacket.

In the colder months, tights or leggings are often a necessity to keep warm! Wear your Chelsea boots with eye-catching patterned or metallic tights or leggings. Check out this cute black velvet babydoll dress with sparkly gray tights!

Dress Down Chelsea Boots

Needing a more casual look? You’ve picked the right boots! Pair up Chelsea boots that are suede, rubbed leather, vintage, or rugged looking with a more formal outfit. Here, this long, airy black dress and chich handbag contrasts well with the black boots that look like they are well-loved.

Jeans…another classic style staple that is known for its versatility. Denim is a great complement for ankle boots and is also a great option when it’s cold out! Below is a cute cold-weather look with skinny jeans, a warm coat, and a knit beret.

Boho-style flowy, feminine dresses, skirts, and kimonos can be worn with rugged, vintage-looking boots for a little bit of edge. Here you can see a pink ruffled dress and pink socks paired with some chunky-soled black Chelsea boots.

Click here to see Skechers’ Women’s Lugnut-Suede Chelsea Boot at Amazon.

Make A Statement Wearing Chelsea Boots

If you’re in the mood to turn some heads, there are lots of ways to play with colors, proportions, and textures when wearing your Chelsea boots.

Add a bright pop of color – Choose one: top, jacket, dress, skirt, tights, or even the boots themselves! Pick any color that will stand out against an otherwise neutral palette – or even a shiny metallic or glitter!

Light scarf with leopard print, Chelsea boots and handbag

Play around with different patterns and textures. If you have shiny, patent boots, pair them with a suede jacket, a chunky knit, rough wool, or patterns such as plaids, bold stripes, polka dots, or even jacquard and brocade for extra fanciness. In this image, neutral grays and blacks are accented with a black and white houndstooth coat.

Click here to see Dr. Scholl’s Women’s Rate Zip Ankle Boot at Amazon.

Play with Proportions – Chelsea boots are known for their clean, minimalist silhouette. Contrast with a voluminous knee-length or shorter skirt or oversized tops such as a chunky knit sweater or boxy coat or blazer. This look pairs sleek Chelsea style boots with a thick sweater and long coat.

Can You Wear Chelsea Boots In The Winter?

But of course! One of the best things about Chelsea boots is their seasonal versatility. However, you want to be mindful about which Chelsea boot style you are wearing on those snowy or icy days. Certain materials such as suede don’t hold up as well to water, and if it’s slippery outside, you will definitely want to choose footwear with traction. With some conscientious planning, it can be easy to stay stylish all year!

Click here to see Dr. Martens Women’s Chelsea Boot at Amazon.

Please also read “Can You Wear Boots In The Summer?” for great style ideas to beat the heat.

How Can You Make Your Chelsea Boots Fit Better?

When you are out shopping, buy your boots true to size; it may be worth getting your feet measured in the store to ensure the best fit. Try on a few different sizes, styles, and brands to really get a feel for the best fit for your feet.

If your boots are or become too loose, try wearing a second pair of socks or extra thick socks. If your boots are too tight, as long as they are made of leather, they may be stretched. This service is usually done at a local cobbler or shoe repair shop, so check around in your area for one of these shops.

After your Chelsea boots have gone through some wear, the side elastics can get stretched out and become too loose. If your boots are otherwise in good condition, you may be able to have the elastics replaced, which will extend their longevity and cost less than buying new boots. Contact your local cobbler or shoe repair shop (or even the boots’ manufacturer) to see if they offer this service.

A shiny black Chelsea boots

Chelsea Boots For Every Occasion!

As you have seen, Chelsea boots are a stylish, versatile wardrobe staple that can be worn for many different occasions. Now that you have gotten some great ideas for ways to wear them, why not try and put together some outfits from your own wardrobe? Have fun, and stay stylish!

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