Blog > News

How to wear Chelsea Boots

Your favourite Chelsea boots outfits are not limited by season and can be paired with so many wardrobe favorites. Whether you are on a countryside stroll, spending a leisurely day in the city, or just out with friends or family, this classic ankle boot never fails. The style and comfort that a Chelsea boot brings is one your feet shouldn't miss out on. These seemingly casual shoes are an all-season star as they pair perfectly with pants, skirts and dresses. Plus, the best part: with our Merino Wool Lined Chelsea Boot, you’ll never have to sacrifice comfort or warmth for that trendy look.  

Table of Contents

What Are Chelsea Boots?

The History Of The Chelsea Boot

Stylish Chelsea Boots Made Of Merino Wool

5 Effortlessly Stylish Chelsea Boot Outfits

What are Chelsea Boots?

The famous Chelsea Boot has epitomised the ankle boot. It is doubtful you’d have to head far before spotting someone parading about in a pair! Instantly recognizable with two elastic side panels, they boast versatility and simplicity, which is why they are so popular with both men and women all over the world. Characterized by:

       Often a pull tab on the rear to make it easy to take them off and on

       Typically a very low heel and flatter sole

       Normally a more rounded toe rather than pointed

       Defined by two elastic looking side panels

The combination of practical elements makes them an all-purpose shoe for every and any season - there is no reason you cannot wear them all year round!

The history of the Chelsea Boot

Chelsea boots have a long and rich history dating back to the Victorian era. In 1830, a man named J.S. Hall, who was Queen Victoria’s shoemaker, originally designed the boots for men in - you guessed it - Chelsea, London. Hundreds of years later, you now see both men and women sporting the boot throughout the year.

What made them a great success, all those years ago, was the pull tabs on the back of the boot. This ensured they could be put on with ease, in comparison to traditional boots that you had to tediously lace up. As well as this, the boots’ classic elastic paneled sections were, at the time, an innovation to the footwear industry.

Throughout the 1960s, the Chelsea boot rose to fame again when the The Beatles wore them as part of their outfits for their staged concerts. Nicknamed the “Beatle Boots”, the original Chelsea boot was adapted to have a pointed toe and a higher heel section. After seeing them be worn by famous musicians, everybody wanted a pair of stylish Chelsea boots for themselves. From this point on, the boots have never gone out of style and the rest, as they say, is history. 

Stylish Chelsea Boots Made Of Merino Wool

Merino wool has many amazing benefits that make it the perfect material for our Chelsea boots! This special wool has temperature regulating properties, allowing it to create the perfect winter boot. Combined with breathable fibres, it is also summer appropriate, keeping feet cool on warm days and snug on chilly days! If you suffer from sweaty feet, you’ll appreciate the boot’s ability to wick away moisture keeping your feet dry at all times. The structure of the wool also makes it antibacterial so you can say goodbye to smelly odours when they finally come off. 
how to style chelsea boots

We’re often in a hurry and a pair of Chelsea boots that are easy to throw on with any outfit saves time and stress. Even more so with super soft wool lining, allowing you to go sockless and enjoy that barefoot feeling. 


5 Effortlessly Stylish Chelsea Boot Outfits

Classic, girly or edgy: no matter your style or mood, Chelsea boots are extremely adaptive and go great with every outfit. Here are 5 different ideas to inspire your next look or help you express your individual style. 

#1 Chelsea Boots & Shorts

Come rain or shine, you can style Chelsea boots with shorts, to create a chic outfit. Whether you’re pairing with casual or tailored shorts, our Chelsea boots will look incredible! To rock this look in colder weather, wear a pair of black, semi-transparent tights under some cool shorts. If you’re looking for an outfit with a vintage edge, try our boots in the shade “Sandmelé.” 

how to style chelsea boots and shorts

#2 The Classic Chelsea Boot Outfit

The ultimate Chelsea boot outfit is all about keeping cozy. Choose your favourite pair of pants, and wrap up warm in a wool sweater, cozy jacket, and a soft beanie. Finish the look off by pulling on your warm boots, you’ll be ready for all of winter’s adventures.
casual outfit with chelsea boots

#3 How to Wear Jeans with Your Favourite Boots

When pairing your Merino Wool Boots with jeans, your pants shouldn’t be too long—and shouldn’t be worn over the boots. It’s best to opt either for skinny jeans worn inside the boots, or to roll longer jeans up over the top of the boots. For an even cooler look, go for jeans with a fringed hem.

how to style chelsea boots with jeans

#4 Embrace the Dark Side in Chelsea Boots

For those who like creating an air of mystery with their outfit, you may wish to stick to dark tones. Throw on your favourite pair of dark denim jeans, a leather jacket, a simple tee, and a pair of black or grey Chelsea boots. That’s all you need for rocking this look. To add a more feminine edge, opt for a flattering mini-skirt instead of pants.

easy ways to dress chelsea boots and leather jacket

#5 Simple Yet Stylish Chelsea Boot Outfits

Do you tend to wear neutral colours? If this is you, you can let your accessories do the talking. Choose a statement necklace or stylish bag, keeping the rest of the outfit classy with minimalistic Chelsea boots. 

warm chelsea boots for winter

Don’t yet have any Chelsea boots?  Treat yourself to a pair of our Merino Wool boots in our chic Chelsea Style:


About Giesswein

We are a family-owned Austrian merino wool company. Currently run by our third generation of Giessweins our men’s slippers and women’s slippers, as well as our men's sneakers and women's sneakers combine all the wonderful features of wool. This ensures your feet are kept warm, comfortable, and stable at all times. We focus on creating stylish and practical footwear, whilst being conscious of the environment. Recycling 90% of our water, and using raw and renewable materials.