Chelsea boots are must-have boots that can be worn with various outfits. With a timeless design, Chelsea boots have been in style and will remain in style.
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Editor’s note: This post was originally published in August 2019. It has been updated with new pictures and commentary on March 16, 2020.
Table of contents
What’s a Chelsea boot?
Chelsea boots are ankle-high boots that have an elastic side panel and a tab on the back, which makes it easy to slip-on. Since they’re timeless, these refined boots will look great on you regardless of age or personal style.
Related: 15 best suede Chelsea boots
If you need shoes that go with jeans and a t-shirt while also pairing well with a suit, Chelsea boots are the way to go. They’re popular because they can be worn with many different outfits and through various seasons.
These boots date back to the Victorian era, which was between the mid-1800s to early 1900s. J. Sparkes-Hall was the first to design and patent the elastic ankle boot, which is now known as the Chelsea boot.
The word “Chelsea” comes from the South West in London, an area called Chelsea. Aside from its origination in London, the Rolling Stones and the Beatles made the Chelsea boot very popular as well.
Stormtroopers from Star Wars wore white Chelsea boots, too.
They’re great for numerous occasions such as work, weddings, parties, or business meetings. You won’t have to worry about being out of place.
Due to their timeless design, Chelsea boots will be in style now and in the future.
Material and design
When it comes to the material, suede and leather are the most common. Regarding shoe design, there’s plain toe, cap-toe, and wingtip.
Leather
Suede
Wingtip
Cap-toe
Suede or leather?
Both are great options, and you should eventually consider having both. If you’re buying your first pair, I recommend leather because it can be dressed up like a dress shoe and down, like an everyday boot.
Once you have the essential first pair, you can explore other options. You can get another leather pair in a different color or try a suede pair.
Choosing a color
With the variety of colors available, it’s best to stick to simple colors. The following are the best colors:
- Black: Offers a sleek and timeless look.
- Brown: Easily dressed up and down.
- Grey: Great for casual wear.
- Tan: Versatile and great for casual outfits.
- Burgundy: Works for all formalities.
Simple colors allow you to wear it with the majority of your clothes rather than a single outfit. Otherwise, your boots to collect dust, and you’ll feel like you wasted your money because you don’t wear them often.
The goal is to have flow in your wardrobe, which means that it’s easy to put together outfits, instead of having one-off pieces.
The right fit
The following are reasons to try on the boots before deciding to keep them:
1. They don’t have laces: You lose the luxury of tightening or loosening the boot. Therefore, look for a comfortable and snug fit. Also, make sure your toes aren’t squeezed together.
2. Instead of sizing up or down, you’ll have to change the width. This could mean going with a different brand. Finding the perfect fit will ensure that the boots last you a long time while keeping you comfortable.
10 Chelsea boots outfits
The following are 10 ways to wear Chelsea boots:
Grey jeans, corduroy jacket, and black Chelsea boots
A blue corduroy jacket brings back a classic piece in men’s outerwear. The jacket pairs well with grey jeans and looks amazing finished off with Chelsea boots. This look is perfect for a day out or during the fall and winter.
Shop the look:
- Levi’s Corduroy Sherpa Lined Trucker Jacket
- Uniqlo Black T-Shirt
- PAIGE Grey Jeans
- Ted Baker London Black Chelsea Boots
Blue denim jacket, black jeans, and black Chelsea boots
Wearing black jeans, a black shirt, and a denim jacket creates a pop of color, which makes the outfit more interesting.
Shop the look:
- Uniqlo Black T-Shirt
- Calvin Klein Denim Jacket
- FRAME Ripped Black Jeans
- Ted Baker London Black Chelsea Boots
Grey sportcoat, olive green trousers, and black Chelsea boots
With the business casual look, a suit without a tie, you can wear it to business meetings or work. Black leather Chelsea boots work well for this outfit because they’re similar to sleek dress shoes. Although there aren’t any laces, they’re simple and classy.
Shop the look:
- Suitsupply Sport Coat
- Nordstrom White Dress Shirt
- J. Crew Olive Green Dress Pants
- Ted Baker London Black Chelsea Boots
Charcoal grey suit with black Chelsea boots
Chelsea boots are great for formal and business dress codes. Aside from occasions that require a tuxedo, you can pair these boots with a suit and tie.
Shop the look:
Grey jeans, dark grey rain jacket, and black Chelsea boots
Regardless of the weather, these boots will look great. Pair the boots with a classic rain jacket for the perfect rainy day look
Shop the look:
- J. Crew Navy Button-Up (Similar)
- Levi’s Rain Jacket (No longer available)
- PAIGE Grey Jeans
- Ted Baker London Black Chelsea Boots
Black jeans, grey sweater, and black Chelsea boots
One of the essential rules for matching clothes is to create contrast. Wearing a light shirt with dark pants and shoes will do the trick.
Shop the look:
- J. Crew Destination Sweater (no longer available)
- FRAME Ripped Black Jeans
- Ted Baker London Black Chelsea Boots
Blue jeans, plaid shirt, and black Chelsea boots
For a casual yet put-together look, wear jeans and a plaid button-up. It’s perfect for a date or meeting with a friend. If it’s warm, you can roll up your sleeves.
Shop the look:
Grey jeans, blue button-up, and black Chelsea boots
Contrast is a great place to start when you’re putting together an outfit. A dark top, light pants, and dark shoes will create an eye-catching outfit.
Shop the look:
Black jeans, blue short-sleeve shirt, and black Chelsea boots
Black jeans pair well with black leather Chelsea boots. The bottom of your jeans wraps around the top of the boots nicely without making it look weird or feel uncomfortable.
Shop the look:
Olive green utility jacket, black jeans, and Chelsea boots
When it’s cold, staying warm and stylish is the goal. Wearing a military jacket, light sweater, and dark jeans look great during the colder weather.
Shop the look:
- rag & bone Grey Shirt
- Wallace & Barnes Military Jacket (No longer available, here’s a similar one)
- FRAME Ripped Black Jeans
- Ted Baker London Black Chelsea Boots
Buying guide
Before you buy a pair of Chelsea boots, the following are features of a high-quality pair:
1. The zipper: Technically speaking, these aren’t Chelsea boots but a zip-up boot.
2. Nail the fit: As mentioned before, make sure these boots have a snug fit. Often, standard sizing won’t be accurate because these close-fitting boots need to match your foot. The best way to ensure that it fits is to try them on and walk around when you do.
3. Slim soles: For a classic and sleek look, choose one that has a thinner sole. The thick commando soles are great for grip in slippery situations, but a thin sole looks the best.
4. Choose high-quality: High-quality boots may cost more upfront, but it’s worth it. Aside from quality leather, make sure the elastic band is made of solid material and can withstand a lot of wear. The elastic band determines the lifetime of your boots, once that tears, you’ll need a new pair.
Frequently asked questions
Chelsea boots can be worn all-year-round. In the summer, it can get hot and uncomfortable, so make a decision based on the weather. Regardless, they’ll look great with jeans and a tee-shirt or button-up.
Yes, you can wear them with a suit of any color.
Lightweight and thin mid-calf socks do well with boots.
Conclusion
Chelsea boots are versatile and timeless. They deserve a spot on your shoe rack because of the number of outfit combinations that are possible, and they’ll immediately uplevel your style.
More resources:
Photos by David Em/Next Level Gents.
Joshua Steen says
Great article with practical tips on how to incorporate Chelsea boots into your wardrobe. Definitely subscribing. Hope to see more great content.
David says
Hi Joshua, I’m glad you found this article helpful. I appreciate your support!
Muhammad says
Thank you for the info i just bought first chelsea boots it’s really good help me keep posting abiut boots or other things thanks
David says
Hey Muhammad, that is so awesome! I’m glad you found it helpful and congratulations on your first pair. I hope you enjoy those boots.
Jeremy says
what brand are your boots?
David Em says
Hi Jeremy, they’re from Ted Baker.