The best 12 autumn and winter boots for men, from Chelsea to cowboy boots

The season for boots has arrived. From the time of the ancient Egyptians (a pair of boots was found in the tomb of ancient Egyptian chief Qomhotep), although all types of men’s boots were originally designed for a function, whether it’s the military background of desert boots or the stirrup soles of the cowboy breed, today, they offer ample opportunities to show off your own style.

Whether it’s a runway show by Giorgio Armani and Prada or a classic from brands like Grenson and Church, I’ll bring you the boots worth mentioning in this season’s men’s shoe rotation, and I’ll pick the right fit for you.

Chelsea boots

No pair of boots is as attractive as Chelsea’s boots. Originating in the Victorian era, it is highly sought after from the Rolling Stones to Kanye West. It’s no surprise that both glossy and suede are easy to wear and have an elegant look that every man should have at least one pair.

Hiking boots

At the forefront of combining outdoor functionality with fashion trends, humble hiking boots have undergone a serious makeover in recent years. These shoes are now seamlessly integrated from performance elements into shoes that can be worn every day. From Camper and Red Wing, from Prada to Valentino. Given their durability and practicality, it’s an investment that will stand the test of time, especially if you’re hiking at the top of a mountain.

Desert boots

No boot bridges the gap between intelligence and casualness better than desert boots. Clark became popular in the late 2040s, inspired by a military boot introduced during World War II. They are unlined and ultra-durable.

Cowboy boots

The combination of function, tradition and Western romance made cowboy boots the shoe of choice for the rebel generation. Then, in the ’70s, Mick Jagger, Bruce Springsteen, and Jimmy Hendrix came to power, and more recently, Matthew McConaughey. Cowboy boots are now making a comeback in the fashion scene and will inject some rock ‘n’ roll style into your outfits.


This chubby boot became popular in the late 60s of the 20th century, and due to its steel toe cap and sturdy design, it quickly earned itself a bad name when it was associated with skinheads and hooligans. Thankfully, punk rock bands left their mark on boots, and today this style is the perfect shoe to make you look more masculine.

Jodhpur boots

This boot, which has a similar silhouette to the Chelsea boots, was first designed in the 20s of the 20th century as a cycling boot for the sport of polo in Indian cities, hence the name. While some shoes have the same elastic plates as Chelsea’s boots, they are usually fastened with belt buckles to make a particularly chic pair of shoes paired with a pair of slim-fitting jeans.

Best Men’s Boots Recommended


For eternal elegance,


Be your first stop in search of boots. It boasts a complex shape, premium suede upper and a cross with a complete gold-toned clasp. Their sleek pair perfectly with slim-fitting black jeans, while the suede brown hue is perfect for country pubs and outings, meaning they’re boots that don’t lie dormant in the box.



A pair of tall derby boots with 14 eyelets. Don’t be fooled by its size, it’s very lightweight, made from waxy black leather produced by Horween, Chicago’s famous tannery. This is a pair of boots suitable for life, the leather itself has a unique luster, it looks very stylish.


Clarks Originals

Clark desert boots are a classic. However, I am particularly interested in beeswax skin products. Truly iconic style, the tactile upper sits on a rich brown crepe sole with a very good texture!



These Prada boots are sci-fi and futuristic. Made from rubber and leather, with a thick rubber sole and paired with a popular trench coat, the return rate is definitely 100%.


Common Projects

It’s a clean and chic pair of Chelsea boots. Typically minimalist, with a luxurious leather texture and ironed lettering with one of the brand’s signature gold-tone serial numbers, it’s well worth having.


Brunello Cucinelli

Brunello Cucinelli is a traditional hiking-style haute couture boot that takes a classic silhouette and gives it some extremely luxurious appeal. Deep polished and meticulous Italian craftsmanship in dark brown leather, but look at the details and you’ll really see where the value of this shoe lies, from the stitching to the rich brown suede heel tag.



Since 1896, Guidi has been at the forefront of Italian leather craftsmanship. For leather as soft as these ankle boots, 124 years of expertise is exactly what it needs. I especially like the bronze zipper in the middle. In addition, for increased durability, a rubber vibrating sole was chosen.


Giorgio Armani

Giorgio Armani has done a lot of work on this classic, heavy-duty military boot, and the result will add new advantages to your gear and make you stand out for the rest of your boots season. The wrinkled rubber sole amplifies the volume of these shoes to great effect, while the designer’s appeal comes not only from the branded insole, but also from the top of the multi-layer sole unit.


Red Wing

If you’ve been to Shoreditch, you’ll see a lot of boots like this. In the village of East London,

Already a classic outfit for men with perfect mustaches and lumberjack shirts. To be honest, I can understand why. Strong, beautiful and durable (the Tred outsole and Goodyear welt ensure this).



Crafted from a blend of cow and goat leather, these boots from All Saints have a minimalist design aesthetic and also include a chunky sole for added height if you want.


These boots hit the hiking shoe trend, but can be worn casually as a daily casual outfit. The lace-up fasteners and silver-toned eyelets, combined with the perfect shoe shape, are stylish and durable.

[12] Saint Laurent

Saint Laurent’s

These boots have now become an inherent element of the Parisian brand, just like skinny jeans and heavy-duty leather biker jackets. Its classics, even ten years from now, will not go out of style.

Thank you for reading!

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Red Wing