The Best Chelsea Boots for Men 2023

5 Best men's Chelsea Boots 2023The Best Mens Chelsea Boots for 2023

From its Royal roots to the feet of rock 'n' roll rebels, the Chelsea boot continues its reign as one of the most popular choices of men's footwear. 

Chelseas are a versatile, comfortable, and stylish pair of boots that offers a classic timeless look. These boots were first said to be made by Queen Victoria's cobbler, and then took a leap into everyday fashion when King's Road in Chelsea, London took a shine to this particular style of shoes.

The likes of The Beatles and The Rolling Stones then brought an A-list appeal to the Chelsea boot, and, now, they are a firm favourite and wardrobe staple in the modern world.

Hollands have a great wide range of Chelsea boots which are exceptionally comfy, easy to style, and at different price points. Here, we take a look at some of the best out there.


1. Blundstone Classic 585 Boots


Blundstone 585 Boots in Rustic Brown against a white background

These boots from Australian brand Blundstone are a best-seller for a reason. The 585 boots are known by our warehouse as one of our 'in-and-out' products - as soon as they hit the shelves, they fly out and onto their new wearer's feet!

People can't get enough of the Blundstone 585s, and that is due to their combination of all-day comfort and fashionable style. These boots were designed with XRD technology to absorb shock, and their well-known legendary comfort insoles keep comfort to the max. 

With a thick, chunky rubber sole that is durable and built to last, these Blundstone boots are continually met with rave reviews. The full-grain leather fabric has a weathered matt brown finish for a more rustic appearance, these casual boots can be dressed up or down, depending on the occasion.

Pair with jeans and a simple t shirt for an everyday look, or they can be worn with a suit for a special event. Our Hollands Directors also styled these boots with their wedding outfits for the ultimate country look, even on the big day!


2. Hoggs of Fife Stanley Semi-Brogue Dealer Boot


Hoggs of Fife has been creating classic gentlemen's countrywear since 1888, and the Stanley boots are a stunning addition to their collections. 

The trusted reputation that Hoggs has built over time means they are a much-loved brand within the agricultural and farming communities. Their take on the Chelsea boot shows off traditional country style in modern fashion. 

Featuring a hand-stitched Danite rubber sole, which has been made with Goodyear welted construction, these comfortable boots are robust and slip- resistant. The rounded toe keeps them comfortable and stylish, completed with the brogue serration and punching details. 

If you want to impress at the local country pub or when out socialising with friends, these are the perfect boots. They look great paired with your favourite jacket and a classic tattersall shirt


3. Cotswold Siddington Leather Brogue Chelsea Boot

Cotswold Siddington Leather Brogue Chelsea Boot

The Cotswold Siddington is a great alternative if you want the classic style at a lower price. Their modern twist on the Chelsea boot not only looks impressive, but features premium leather soles.

These are a true gentleman's boot, which can be paired with traditional country clothing like a quilted jacket or stylish knitwear. They will quickly become a go-to of your wardrobe; looking great in the modern-day office or brushed up for a more formal dinner. 

We love the contrasting elastic side gusset and rear pull finger loop, which makes it much easier to get the boot on and off. The brogue detail adds a finishing touch to these fantastic pair of boots. If you prefer a commando sole, the Siddington also come in this particular style.

In both brown and black leather, Cotswold show off the Chelsea boot at its affordable best.


4. Dublin Mens Venturer Boots III

Dublin Mens Venturer Boots III

These waxy leather boots from popular brand Dublin are a great addition to your Chelsea boot collection.

A pair of Chelsea boots are irresistible in terms of their style and look; so much so that you will want to wear them all day, which subsequently means you need them to be as comfortable as possible! The Venturer boots have been designed to be just that. 

Their moisture-wicking RCS footbed system keeps the boots breathable, and the elasticated ankle creates a comfy fit for the wearer. The rugged rubber outsole makes for quality grip, and the leather upper is exceptionally attractive.

The brown or black leather can be styled with slim fit dark jeans, a leather jacket, and accessories for a classic sleek look that plays on its rock 'n' roll heritage. Alternatively, keep it weekend casual with a button-down shirt and blue denim


5. Hunter Mens Commando Chelsea Boots

Hunter Mens Commando Chelsea Boots

For your more cold-weather adventures, we love this modern take on the Chelsea boots by Hunter.

Fully waterproof with a hardier tread, this pair of boots also features an elastic side gusset and a nylon pull tab. Crafted using natural rubber from forests independently audited to Forest Stewardship Council® standards, and with an updated recycled polyester lining and insole, these Hunter boots are essentially Chelsea boots 2.0.

Suitable for wet conditions, these waterproof boots are a happy medium between short wellies and typical Chelsea brogues. They help to keep your feet dry if you're heading out on rainy days, and they have taken their firm place in our top Chelsea boot picks. 

Pair with slim fitting waterproof trousers for more weather protection, or slip on with your jeans and simple tee if you just want to make sure your feet are protected on strolls in the countryside. 



These Chelsea boots showcase some of the best in our collection, but we have plenty more for you to choose from. 

Blundstone have a wide range of enviable Chelseas, with even thermal lined boots that make a great alternative to a pair of winter boots. Chelsea boots with a steel toe cap, like the ones from Grafters, make for ideal work boots, and if you're looking to treat a woman in your life, Dubarry have a premium waterproof pair of boots. We have kids choices too, for those little feet which have caught the Chelsea boot bug early!

Make sure you look after your new pair of Chelsea boots, by giving them a little TLC every so often. Try treating them before your first wear as well as regularly restoring them over time. We would suggest either the Hoggs Wax Leather Balm, which will nourish the leather with essential oils and waxes, freshening the appearance and preventing the leather from drying out and cracking, or the Nikwax Fabric and Leather Proof Spray.

As ever, if you would like any further advice on these boots, or any other Hollands product, don't hesitate to get in touch with our customer service team via email or phone. 

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