We understand guys have questions about what to wear (and how to wear) their favorite pieces.Stick with us all this week to get advice on how to look good, stay fresh, and even score a date. This is Complex Style's"How To" Week.
While the Chelsea boot is a style that's over 150 years old, it's become a contemporary favorite for guys today. The boot's inherent simplicity lends itself well to a variety of looks, and if the several celebrity co-signs weren't enough, we can safely say that it's a very easy boot to assimilate into your closet.
But considering that this silhouette hasn't seen this much play since the Beatles and The Rolling Stones were on the radio, guys have been wondering how to add this '60s staple into their modern-day wardrobes. Fear not, you don't have to dress like they did 50 years ago in order to pull this off (unless you're Hedi Slimane). Sure, it was one of the biggest trends of 2014, but we've broken down what you need to know and look for when you're wearing your Chelseas. This is How to Wear Chelsea Boots.
They should fit snug, but not tight.
Learn the different styles of boots out there.
To state the "standard," a traditional Chelsea boot is made of black (or occasionally brown) boxcalf leather, with a leather sole. That said, over time, variations have emerged that are similar to the Chelsea boot, but wouldn't technically go by that name.
There are subtle differences that have cropped up to cater to a contemporary market. Here are some of the basics:
A commando sole (basically a rubberized sole with treads) is common, especially for people who are looking for a Chelsea boot that can handle snowstorms and tough weather.
Jodphur boots share the horse-riding origins with the Chelsea boot, but have a wrap around buckle closure instead of elastic side panels. As mentioned before, for some Chelsea boots, zippers may also be added in place of elastic sides. Even with all this variation, forChelsea boots, less is more. Keep it minimal, and you're going to be that much closer to an authentic Chelsea boot.
Zip ankle bootsare named for the side or back zips that appear in place of elastic to help keep the boots on your feet. It's a less classic option, but equally versatile for a pair of Chelsea boots. While zippers help with fit and flexibility, these boots are technicallynota trueChelsea boot, at least tomenswearpurists. But it's not wrong to kick around in a pair either, plenty of times they offer a cleaner shape than traditional Chelseas.
Broguing is the technical term for the "wingtips" on your wingtips. The perforated designs are all a matter of personal preference, but they're not necessarily ugly—just not as popular as the smooth silhouettes you see on stylish dudes all over the place these days.
Leather boots are easier to care for than suede, but suede looks more luxe.
When it comes to design, less is more.
You really get what you pay for.
Your pants should cover the top of the boots.
Two easy ways to wear them: with denim or proper pants.
Chelsea boots are extremely versatile and can be worn with both formal and casual outfits. Invest in a high-quality pair in a classic color, and you'll be able to combine the same pair of boots with jeans or a suit as the simple and clean lines of Chelsea boots complement most outfits.Should I buy Chelsea boots a size bigger? ›
Buy your correct size and no bigger.
Chelsea boots are normally true to size, so there's no need to size up or down.
The most versatile boot for stylish men. Chelsea boots have quickly become a must-have in the leisure wardrobe of any discerning gent. Whether for a wintery weekend or a casual dinner, they're the ultimate shoe when it comes to style and versatility.Are Chelsea boots for everyone? ›
While other boots go in and out of style, the Chelsea boot has remained at the forefront of fashion. Due to their versatility and classic style, both men and women have favoured them since the '50s and '60s.Do Chelsea boots go over or under jeans? ›
You can cuff your jeans or let them fall over your boots. Cuffed jeans give your outfit a more polished look, while letting your jeans fall over your boots gives your outfit a more casual look. Socks...or not: You can wear socks with Chelsea boots or go sock-less.Should jeans be tucked into Chelsea boots? ›
When wearing your Chelsea boots with trousers or jeans, keep your trousers over the boot. Do not tuck your jeans into the boots. Not only will this ruin your entire look, but it will also stretch the boot out so that it doesn't fit you correctly anymore. Suede boots are ideal for a comfortable and casual look.Should Chelsea boots be snug or loose? ›
Slip on Chelsea boots should have a snug fit. The pull tugs at the front and rear of the boot, combine with the elasticated sides to make it easier to put your boots on and take them off while ensuring a snug, comfortable fit in wear.What is the best color for Chelsea boots? ›
Brown in all shades is ideal for a pair of Chelsea boots, since it can be easily dressed up or down. If you want to go formal, pair your Chelsea boots with suits in mid to and light tones for the best results.How do I know if my Chelsea boots are too big? ›
The Toe Box
You want your toes to have room to breathe, but not so much room that the boots are sliding against your feet. A good rule of thumb is that you want about a half an inch of space between your longest toe and the toe box.
Therefore, jeans shouldn't cover the boots. That's why cropped jeans, which let a little skin peek out between the shoe and the trousers, are perfect for an everyday look. If the trousers are too long, simply roll them up casually to make the look even more casual. From skinny to straight - anything goes with Chelseas.
Slim fit jeans offer a flattering shape that is perfect for pairing with Chelsea boots. The slimmer leg style tapers towards the ankle, so your jeans can sit perfectly with the top of your boots. It's a casual style that looks sharp and well-polished, as well as being practical and easy to wear.Are Chelsea boots still in style 2023? ›
Women's Chelsea boots are always in style, making them a timeless addition to any wardrobe. As we dive into the latest fashion trends of 2023, Chelsea boots are emerging as a popular choice in footwear.Can you walk in Chelsea boots all day? ›
"Since most Chelsea boots are flat, they are a great option when you need to be on your feet all day or you are traveling," Cramer said. "They are also a perfect choice for city living.What season do you wear Chelsea boots? ›
Wide or narrow feet, Chelsea boots are suitable for all body types and can be worn all year round! Although they are ideal for keeping feet warm and dry in winter, they will also dress up a more summery outfit in spring.Are Chelsea boots supposed to be loose at the top? ›
Slip on Chelsea boots should have a snug fit. The pull tugs at the front and rear of the boot, combine with the elasticated sides to make it easier to put your boots on and take them off while ensuring a snug, comfortable fit in wear.