Chelsea boots are must-have boots that should be in every man’s wardrobe. This guide will show you exactly how to wear Chelsea boots from casual to formal.
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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 January 31, 2020.
Contents:
- What’s a Chelsea boot?
- Why you need Chelsea boots
- Material and design
- What color should I get?
- How should Chelsea boots fit?
- 10 ways to wear Chelsea boots
- Wearing Chelsea boots in the summer
- How to buy Chelsea boots
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. These boots date back to the Victorian era, which was between the mid-1800s to early 1900s.
The word “Chelsea” comes from the South West in London, an area called Chelsea. Aside from its origination in London, the Beatles made the Chelsea boot very popular as well.
Stormtroopers from Star Wars wore white Chelsea boots, too.
Why you need Chelsea boots
If you need a pair of shoes that goes with jeans and a tee but also pairs with a suit and everything in between, Chelsea boots are the way to go.
Versatility
Chelsea boots are an absolute favorite type of boots for many guys out there. They can be worn with many different outfits and through various seasons.
These boots are also great for various occasions. You can wear them to work, weddings, casually or to business meetings. Whatever the occasion, you can wear Chelsea boots without being out of place.
These boots can be worn so many times throughout the year, making them a must-have pair of boots. Invest in a high-quality pair and it will be so worth it.
Classic and timeless
The best thing about the Chelsea boot is that you won’t have to worry about it going out of style. It’s been around for over 150 years!
They are timeless shoes and you’ll be able to work it into your wardrobe for any season. This year and five years from now.
Classic and timeless. They are two characteristics that you really want to think about when it comes to your clothes.
Sure, something can be trendy for a short amount of time but items like Chelsea boots are proven to stick around. That makes them worth investing in.
Chelsea boots will be in style now and in the future as well.
Material and design
When it comes to the material in which Chelsea boots are made, suede and leather are the most common. As far as shoe design, you’ll find plain toe, cap-toe, and wingtip Chelsea boots.
Leather
Suede
Wingtip
Cap-toe
Suede or leather?
Along the journey of your search, you will find Chelsea boots in a few different materials. Such as suede and leather.
Both are great options and you should eventually, consider having both in your footwear rotation.
If this is going to be 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.
What color should I get?
You can buy Chelsea boots in many colors. Although there is a great variety, it’s good to stick to simple colors.
The best Chelsea boot colors are:
- 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.
By having these colors, it allows you to wear it with the majority of your clothes rather than having a shoe that can only go with one single outfit.
Not only will that cause your boots to gather dust, but you’ll also feel like you wasted money on boots you don’t even wear that often.
These colors also allow for great versatility, which is important when you are building a wardrobe.
You want to have flow in your wardrobe – meaning that it is easy to put together outfits, instead of having one-off pieces.
How should Chelsea boots fit?
When buying these boots, you should try them on. Here are the reasons why you need to try them on before deciding to keep them.
1. They don’t have laces. This means you lose the luxury of tightening or loosening when a shoe doesn’t fit well.
When you try these boots on, you have to make sure they fit and are comfortable.
The fit you’re looking for is a snug fit and you don’t want your toes to be squeezed together.
2. Instead of sizing up or down, you’ll have to change the width of the boot. This may mean going with a different brand and that is okay.
Finding the perfect fit will ensure that the boots last you a long time while keeping you comfortable.
10 ways to wear Chelsea boots
Chelsea boots can be worn with jeans in a skinny or slim fit and with dress pants. Below, I will show you different looks to style the same pair of black Chelsea boots.
Take a look at the outfits prepared for inspiration and try it out. Combine outfits to your liking and you’ll figure out how to style Chelsea boots for you.
Once you get used to wearing Chelsea boots, you’ll find yourself wearing them very often. They are a great pair of boots that can be worn with a variety of outfits, which makes them essential.
Same boots, many different ways to wear it.
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
In this outfit, I went with a light blue denim jacket and black everything else. This allows the denim jacket to have that 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 are very similar to sleek dress shoes. Although there aren’t any laces, they are 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 fancy, dapper and business dress codes. In this outfit, we put together a charcoal suit with black leather Chelsea boots.
Shop the look:
Grey jeans, dark grey rain jacket, and black Chelsea boots
If it’s raining out, don’t worry. That doesn’t have to stop you from wearing these stylish boots.
These boots also pair well with a rain jacket on top. In this outfit, I wore a button-up, grey jeans and topped it off with a black rain jacket.
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
This outfit creates a ton of contrast which makes an outfit eye-catching. It is a very simple and easy outfit to put together. Yet, with the Chelsea boots – it looks so sleek.
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
With slim fit jeans and a plaid button-up, it creates a more casual look. Not too casual but perfect for a date, meeting with a friend or just being out and about.
This outfit is perfect for summer days since you can roll up your sleeves if you get a little too hot. It’s also perfect for an overcast day where it isn’t too cold or too hot.
Shop the look:
Grey jeans, blue button-up, and black Chelsea boots
The dark top and light bottom pairs well with black leather Chelsea boots. There is contrast, which is always a great starting point and the boots make this a little bit more formal.
Shop the look:
Black jeans, blue short-sleeve shirt, and black Chelsea boots
The skinny jeans offer a more trendy and hip look yet still good for an everyday outfit.
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
The overshirt, with a sweater, black jeans, and black leather Chelsea boots make for a great colder weather outfit. Not only will you stay warm, but it’s also very stylish.
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
Wearing Chelsea boots in the summer
Chelsea boots can be worn all-year-round. In the Summer, it can get hot and uncomfortable so you’ll want to make a decision based on the weather.
In the Summer, Chelsea boots look great with jeans and a tee-shirt or button-up (long and short-sleeved).
How to buy Chelsea boots
Before you buy a pair of Chelsea boots, let’s take a closer look at important features of a high-quality pair of Chelsea boots.
1. The zipper: You’ll find “Chelsea boots” with zippers instead of the elastic band. Technically speaking, these aren’t Chelsea boots but simply a zip-up boot.
2. Nail the fit: As mentioned before, make sure these boots have a snug fit. Oftentimes, 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 a Chelsea boot 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: A Chelsea boot made of high-quality material may cost more upfront but it’s worth it. Aside from high-quality leather, make sure the elastic band is made of great material and can withstand a lot of wear. The elastic band determines the lifetime of your boots because once that tears, you’ll need a new pair.
Conclusion
Chelsea boots are versatile and timeless. They deserve a spot in every wardrobe because of the number of outfit combinations that work with them and they’ll immediately uplevel your style.
Additional style resources
Want to learn more about Chelsea boots, or what to wear with them? The following are a few additional 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.