Reviewed & updated: October 19, 2022 by Jamie Wilson BA
Many fashion brands are coming out with Chelsea boots nowadays. Are you looking for some fancy footwear? These boots are usually worn to the office & during the fall season, as well as in the winter. Do you love to style leather boots in different ways and when trying out a smart casual outfit? Well, the truth is that they look beautiful when paired along with a simple sweater & a blazer on top! If you need to look into some outfits we have 8 cool styles for you to choose from. These will suit both formal & casual venues, just keep on reading and see for yourself!
Should Chelsea Boots Be Loose?
Chelsea boots should be worn in a specific way; and no, it is not loose. Although you can probably pull off many shoes loose around your ankle, Chelsea boots should fit perfectly & tightly. It should be tight around the leg, but it should still have a bit of space for your toes. You should rather wear & purchase these boots in one size up so that way you can easily throw on a pair of socks underneath your classic boots.
Can You Wear Chelsea Boots With Chinos?
Here’s the thing, you can wear your chinos trousers with chelsea boots. However, it is important to wear different colored clothing pieces with one another. You should pair along your favorite grey pants & a pair of black leather chelsea boots. You can also go for bright beige shoes, but make sure your pants are in any other color. Mix & match these colors so that your pants are always different colored than your shoes.
Top 8 Ways How To Wear Chelsea Boots
1. Grey Coat With Black Jeans & Black Shoes
If you want to look like your favorite celebrity make sure you dress up! Throw on your favorite grey coat on top and wear a stylish blazer underneath. A pair of chelsea boots in black color, along with dark pants will look amazing for both casual & formal events. This shoe is a must-have, especially during the winter. Black chelsea boots are for those who want a comfy outfit that is somewhat easier to style and pull off. In the end, you can also throw on some skinny jeans and make your black boots cohesive the right way.
2. Suede Chelsea Boots With Brown Street Style Jacket
If you are someone who prefers brown elements & you love chelsea boots pair them along with a leather brown jacket as well as a brown bag. Go for a pair of classic black jeans underneath and add a stylish watch to complete the fit. This look is mostly worn by men in their twenties as well as those who don’t mind the attention. Cool brown boots such as these have that ’60s vibe, but are slowly getting that needed popularity these days. Ankle-high boots and the right bomber jacket will speak for themselves. Want to try out this trendy fit yourself?
3. Ankle Boots Dress Shirt With Smart Casual Coat
A pair of leather chelsea boots will keep your feet protected & dry during fall. Chelseas will also give you confidence which will attract women in a heartbeat. If you are someone who loves to follow all the trends & you need some stylish menswear staples you will want to ”subscribe” to this outfit! Want to look sharp from head to toe? Just make sure that the tops of your boots are clean when rocking this style. Guys who are in their 30s will like this fit and style the most.
4. Brown Leather Chelsea Boots With Black Jeans
Guys who are still in school and who would like to throw on a pair of chelsea boots without reaching for some smart black, navy or grey blazers can go for a chill & relaxed fit. Simply pair your boots with some blue or black denim pants & enjoy feeling comfy for hours! These boots can be worn (and should be worn) with a simple shirt, or with a sweater on top if it is a bit chilly outside. When rocking aa black outfit you can also throw on a black leather jacket on top. Enjoy the all-black bad-boy look and know that it is a full strike.
5. Black Street Style Outfit With Suede Chelsea Boots
If you are wondering how to wear a black outfit with some white or beige simple shoe options; go for chelsea boots. They can look mesmerizing once paired with a darker outfit and will add a mysterious vibe to your look. If you are into mono colours choose these two and wear your outfit to your next big date. Guys can also throw on a white t-shirt underneath to enjoy a smooth yet cool outcome. Men who want something lightweight for warmer days will fancy this fit, that’s for sure.
6. Ankle Boots For Dress Up Suits & A Formal Blazer
If you are off to a wedding or if you are the groom know that chelsea boots can come in handy. They add a cool vibe once paired along with a dark suit, as well as with a white dress shirt underneath. Make sure your grooming skills are on point before you throw on this dark purple suit top since it is essential to look presentable. Guys who love colorful & interesting outfits will enjoy this one. You can also throw this fit on if you’re off to a job interview and if you’re out for a formal dinner.
7. Black Outfit With Brown Leather Chelsea Boots & Brown Bag
A simple black outfit with ankle boots is sophisticated & appropriate for any event. If you prefer to shop for monochromatic clothing items, and you want to make your feet pop, invest in these boots. They are sophisticated & will grab attention wherever you go. They are also comfy and will serve you during your everyday classes, work hours, or strolls around the city. Embrace your inner rapper boy or hip hop lover and rock this silhouette.
8. Smart Casual White Jacket With Black Jeans & Leather Chelsea Boots
A stylish white jacket is something that guys wear whenever they need to emphasize their upper body portion. The best way to wear this jacket is with ankle boots in black, your handy bag, as well as some jewelry. Men who don’t know how to look business casual should know that this outfit speaks their language! Throw on some sunglasses as well as confidence and you’ll be all good to go! This fit is a true London playboy vibe, do you dare to fancy it yourself?
Can You Wear Chelsea Boots In Summer?
It is possible to wear your favorite ankle boots with summer outfits. Although it is an unusual combination, this outfit can work when worn to casual events. Also, make sure you go for it only if you live in an area where it is never over 20-25 degrees Celsius. This outfit can make sense if you need to dress up and you need a true gentleman fit. However, if everyone else around you is wearing flip flops maybe you should put this idea on hold for the time being. Rather go for a deep V-neck top along with some stylish sneakers.
What Goes Well With Chelsea Boots?
A short answer – everything! There are no rules since pretty much anything within your wardrobe can look good. Do you want comfort or are you aiming for boots for formal occasions? Simple rules to follow and go along with are:
- Throw on any type of brown suede. Brown, khaki, beige or other shades will work so well with your chelseas. If neutrals are your go-to, this is a must-try outfit. Aim for a simple T-shirt if you’re aiming for that cool casual look.
- Try out a cool oxford shirt. Do you want to look well-put in your navy suit or grey suit? Throwing on a smart shirt and proper leather shoes will look business casual.
- Do you own pretty fancy dress shoes? Do you want an elegant look? Go for a smart collar shirt and dress pants to style chelsea boots. This will suit formal attire.
On That Note
Thinking of investing in a pair of Chelsea boots? Once you read through our guide & follow our set of rules you will easily find the perfect outfit from day-night. The traditional Chelsea Boot is timeless as well as easy to style, as long as you choose one out of our 8 stylish options. Make sure your boots are always tight around your ankle & never forget to color coordinate your outfit.