It’s that time again where our favourite summer shoes retreat to the back of the wardrobe for another year, and boots become the new-season staples.
One of our favourite boots for the winter transition? The classic men’s Chelsea boot. The best Chelsea boots are sturdy and versatile– perfect for tackling any weather and fitting with any outfit. At Wynsors, we’ve made sure to stock up on the latest smart and comfortable styles at our signature incredible prices. So, keep on reading to see our edit of the best Chelsea boots for men this winter.
What are Chelsea boots?
First things first, what exactly are Chelsea boots? They are a smart style of ankle boot with an elasticated side panel and often a pull tab on the back, making them easy to slip on and off. Whether you opt for a leather or suede pair in popular hues such as black, brown, tan or navy, the Chelsea boot is timeless, and promises to take you effortlessly throughout the seasons for years to come.
Most comfortable men’s Chelsea boots
On the hunt for the most comfortable men’s Chelsea boots? If comfort is your top priority, these Cotswold Snowhill Chelsea boots are the ones for you. Lined with a warm faux fur and featuring a waterproof leather upper, these shoes will leave you feeling cosy all day long. Whether you require a boot to keep you comfortable on your feet all day or you’re looking for a casual weekend shoe, these Chelsea boots are impossible to resist – with huge savings off the RRP. Brown isn’t the colour for you? Opt for a black pair instead.
Best black Chelsea boots for men
Speaking of black Chelsea boots, if you want to smarten up for winter, then this pair from Bandwagon are perfect. Finished with traditional brogue details and a wingtip toe, these stylish boots make elevating your A/W wardrobe easier than ever – and they’re also available in tan. Whether you choose to wear them for work or weekend adventures, embrace a sophisticated silhouette this season and put your best foot forward!
Best men’s Chelsea boots for walking
Calling all walking enthusiasts! Next up on our list are the Worcester Chelsea boots from Cotswold. Crafted from premium nubuck leather with a darker finish on the heel and toe, featuring a waterproof upper and an elasticated panel – these versatile boots are built to last. No matter what conditions are thrown at you! Whether you’re tackling the rugged countryside or simply going for a family stroll in the local park, these boots will have you looking and feeling the part.
Most affordable men’s Chelsea boots
For the best cheap Chelsea boots, the classic Liam boots from Bandwagon take the biscuit. Their smooth finish makes them perfect for matching with any outfit – whether you’re opting for a business fit or dressing up for a special event. Comfortable and stylish, whilst being kind to your wallet, this pair will cost you just £35. So, you can enjoy a beautiful design at a great price – also available in tan.
Best brown Chelsea boots for men
If a classic style is your go-to, you won’t want to miss out on this season’s Masada Chelsea boots from Base. This premium-made boot takes on the traditional Chelsea–boot styling with a soft suede upper for year-round wear. Featuring dual pull tabs to help with putting on, and a stitched leather rand for added character. If that wasn’t enough, this pair also features a cushioned foam insole and cosy microfibre lining for ultra-comfortable wear. Available in a muted, medium-brown shade, style them with jeans for casual, daytime wear or dress them up with some tonal chinos for the evening.
Best men’s Chelsea boots for work
We’re loving the classic black this season (can you tell?!), and this pair is no different. Made from a beautifully rich, dark leather, the Northwest Territory Wells boot makes a welcome addition to any winter footwear rotation. Our pick for the best men’s leather Chelsea boots, this simplistic pair has been designed to a tee, featuring low-key branding and minimal stitching on the elastic panel for that extra bit of luxury. Available in tan and brown too!
If your job requires spending time outside, these boots are just as practical! The waterproof, hydry lining offers great protection for those outdoor terrains. However, if you’re in search of a more hard-wearing and protective shoe, browse our selection of safety boots.
Best casual Chelsea boots for men
Here at Wynsors, we’ve got you covered, with boots that make casual feel as good as smart. Originally designed as a safety boot to protect your feet, the Tradesafe Crazy Chelsea boot will give you that authentic Chelsea boot style with a laid-back twist. The signature boot is paired with a lightweight heel and a horse leather upper in a perfect tan shade to fit with any relaxed outfit!
(Psst! Add these quality boots to your basket pronto to bag a pair for just £40!).
Best everyday Chelsea boots for men
Searching for the best everyday Chelsea boots? Cue the Cotswold Bodicote boots. Known for being inspired by the rolling hills and terrains of the Cotwolds, these rugged Chelsea boots are perfect for everyday use. The nubuck leather upper and chunky hardwearing sole makes them a sure thing to withstand the test of time, and easily become your favourite go-to pair!
The greatness doesn’t end there. You can also find this timeless shoe in a rustic brown.
Best dress Chelsea boots for men
For the best dress Chelsea boots, take a look at the premium-made Base Utah boots. The deep-brown leather is waterproof and, when combined with a breathable inner lining and lightweight sole, you have a superior Chelsea boot that offers style & functionality. Practicality aside, this brilliant boot also features stitch detailing around the leather base and a narrower elastic panel for a modernised take on this classic silhouette. For a brighter shade that the modern man may favour, opt for the tan style instead.
Quality boots need quality care, so make sure you follow our guide to polishing leather shoes to keep them looking as good as the day you bought them.
Best men’s suede Chelsea boots
Taking the title for the best suede Chelsea boots, Base strikes again with their all-suede Nelson boots. A slim, lightweight shoe – these boots showcase a sophisticated, designer style at an affordable price. Their ultra-soft, suede finish makes them ideal for a winter wardrobe. A versatile pair that also comes in tan and brown, pair with jeans or smart trousers for an simple outfit that will never fail to impress.
Worried about keeping the suede in tip top shape? Read our guide to cleaning suede boots for expert tips on taking care of these boots throughout the colder seasons.
So, there we have it! Our best men’s Chelsea boots to welcome in the winter season. Browse our complete collection of men’s Chelsea boots here at Wynsors, or for more help and advice head over to our blog.
