Last updated on November 9th, 2022 at 09:43 am
Chelsea boots are the quintessential autumn and winter shoe. Practical, stylish and, most importantly, comfortable. It’s no wonder they’re such a go-to.
The design first hit the streets in Victorian England as a fashion boot for men, though everyone soon adopted the trend. Conveniently elasticated, rather than laced-up, it seems we love a pair of easy throw-on boots as much now as we did back then. It wasn’t until the 1950s and ‘60s that they got their signature name and status. A firm favourite among fashion trailblazers such as Mary Quant and The Beatles, the Chelsea boot’s vintage charm is just as timeless today with a pair of tailored trousers or a mini skirt.
Read on as we style out how to wear Chelsea boots with various outfits, whether you’re transitioning into your seasonal wardrobe or looking for the perfect evening boots.
What’s on this page
- What to wear with Chelsea boots
- How to wear women’s Chelsea boots
- How to wear men’s Chelsea boots
- Chelsea boot style tips: FAQs
What to wear with Chelsea boots
Chelsea boots are as versatile as they come. They’re an easy way to elevate just about any outfit and are great for taking you from day to night. Similar in style to Jodhpur riding boots, Chelsea boots are great for giving off a rustic feel too. Pair them with cuffed jeans, a smart top, and a tailored (or oversized, depending on your preference) jacket and you’re onto a winner.
Opt for earthy neutral tones of chocolate, tan, and black for an understated yet classic look. Brown suede Chelsea boots work really well for this. What’s more, Chelsea’s are smart enough to wear at work, too. Basically, they’re the perfect boots for a capsule wardrobe.
How to wear women’s Chelsea boots
Knowing how to wear women’s Chelsea boots is key to an effortlessly stylish cold season. But the beauty of the Chelsea boot is that it’s hard to get wrong. Follow our guide below for a few style tips and suggestions.
Chelsea boots look great with:
- Midi dresses and a leather jacket
- Boyfriend jeans and an oversized jumper
- Mini skirt and tights
- A pinafore and a long coat
- Straight leg jeans and a white tee
A good pair of boots are a year-round staple, but there’s something to be said about Chelsea boots and cosy outfits as the seasons get colder. Here are some of our top picks this autumn and winter.
Lilley Women’s Black Chelsea Boot Pull On Boot
This classic pair of pull on Chelsea boots from Lilley are ideal for heading to the office or popping into town. Endlessly versatile, the black synthetic leather will serve you well for a range of outfits and occasions.
Lilley Women’s Black Chunky Chelsea Boot
Heading into chunky territory, these black chunky Chelsea boots from Lilley are sure to kick up a storm. Don them with your favourite jeans or a patterned dress to truly embrace the changing seasons. Accessorise with tights or knitted socks peeking out the top.
Lunar Boho Women’s Black Chelsea Boots
Enjoy a hint of pattern with these chunky black Chelsea boots from Lunar. Complete with subtle leopard print sewn into the elastic, these boots look great with high-waisted blue jeans and a leather jacket. The elasticated gusset also makes them easy to throw on for a spontaneous evening out.
Lilley Women’s Tan Chelsea Boots with Buckle
Go for a softer look with these brown leather Chelsea boots from Lilley. Featuring a subtle buckle accessory and a super comfortable sole, this pair is perfect for making a statement whilst also keeping your feet comfy. The soft tan colour also provides a classic look – a great investment for an autumnal wardrobe.
Rieker Women’s Black Multi Printed Chelsea Boot
These printed Chelsea boots by Rieker are striking and stylish, featuring a multi-coloured floral print for a pop of colour. Easy to slip on and go, the chunky heel keeps your feet supported while you take on the day.
How to wear men’s Chelsea boots
Wondering how to wear men’s Chelsea boots? The good news is they have a wealth of history to take inspiration from. The style of men’s Chelsea boots today varies slightly from those popular back in the 50s and 60s. Nowadays, these timeless staples are more about flat, durable footwear with a solid yet comfortable sole to protect against the elements.
Men’s Chelsea boots look great with:
- Dark jeans and a neutral sweater
- Smart jeans and a casual button-up shirt
- Tailored trousers and a blazer or long coat
- Distressed jeans and a white tee
- Mid-wash jeans and a corduroy jacket
Check out our top picks for men’s Chelsea boots this autumn and winter.
Beckett Men’s Chelsea Boot in Tan
Feel supported by the soft synthetic leather of these tan Chelsea boots from Beckett. Fitted with an elastic gusset, they’re easy to pull on and take off. Ideal for heading to work, going out for drinks, or a smart casual event.
Cotswold Farmington Men’s Chelsea Boot in Black
Famous for their durable footwear, enjoy style and practicality combined with these black Chelsea boots from Cotswold. Made with genuine leather, they also have a thick sole to support underfoot. These boots are waterproof, preparing you for all weather and occasions.
Beckett Men’s Black Chelsea Boot
A classic rendition of standard black Chelsea boots from Beckett, these boots are smart and functional for both casual and formal occasions. The textured outsole offers plenty of grip in varied conditions, making them the ideal transitional shoe into winter.
Red Tap Bamford Men’s Brown Leather Chelsea Boot
Warm-toned and versatile, these brown leather Chelsea boots from Red Tape exude sophistication. Great for pairing with tailored trousers and a suit jacket, or dressing down with straight leg jeans and a sweater. Made for comfort and style.
Cotswold Siddington Men’s Leather Boot in Black
Equip your wardrobe with a pair of refined black leather Chelsea boots from Cotswold, complete with Brogue detailing and a contrast sole. Made from premium materials with a designer touch.
Chelsea boot style tips: FAQs
What jeans are good for Chelsea boots?
Due to how versatile they are, knowing how to wear Chelsea boots with jeans is pretty straightforward. They go with just about any slim or straight-fitted jeans that will complement their silhouette. Go ahead and try them with skinny jeans, straight leg jeans, boyfriend jeans, cropped jeans, or even cuffed relaxed jeans to emphasise the boots. Perfect for dressing up and down.
When should Chelsea boots be worn?
Chelsea boots are most in their element during autumn and winter, although they also look great all year round as an evening shoe. You can’t go wrong with boots in general this time of year – a great match for layers and warm scarves. Whether it’s boots with laces or women’s chunky heeled boots, they’re a seasonal sensation.
Can you wear a dress with Chelsea boots?
Chelsea boots are the perfect neutral shoes, which make them ideal for both dresses and trousers. Wrap up warm with tights, a ‘90s style midi dress, and a knitted cardigan – or pair a cocktail dress with chunky Chelsea’s to start the night on the right foot.
Check out our guide on the dos and don’ts of what shoes to wear with leggings and tights to find out more.
Whether you’re dressing up for an occasion or keeping it casual for a day of autumnal window shopping, Chelsea boots are essential for your seasonal wardrobe. These stylish staples are universally loved by everyone – and rightly so!
Find out more style tips and tricks on the Shoe Zone blog, including the top ten boots for men and women this season.
