Best men’s casual boots


The Chelsea boot design comes from Victorian-era England, but the name comes from 1960s and ‘70s London street fashion.

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Which men’s casual boot is best?

When the weather gets cold and the outdoor elements are less than ideal, a great pair of boots can go a long way. But don’t feel limited to finding boots that are all function and no flair. A solid pair of casual boots can handle the harsh climate while still impressing with style and class. You can wear casual boots for practical reasons while still complementing your wardrobe or standing out in a crowd.

The distinctive Timberland Men’s Davis Square Chukka Boots are the top casual boots on the market.

What to know before you buy men’s casual boots

Boot style

In contrast to winter boots, casual boots are built for more than snow and slush. Ideally, they blend fashion and function. Plain-toe and cap-toe are popular styles for a straightforward build and visual sleekness. Moccasin or square-toe boots are newer, even more casual styles that lean on comfort while boasting striking visuals.

Chukka boots are another style that walks the line between casual and classy, featuring an ankle-high body and open-laced uppers. Chelsea boots are a popular option for all genders as are unisex combat boots — with or without steel toes. Both are attractive and appropriate for some work situations, semi-formal and business casual occasions, and everyday wear.


One reason some people avoid wearing boots is the perceived discomfort associated with the classic style of footwear. However, modern manufacturers are placing higher emphasis on comfort. Supportive soles, warm or plush linings, padded collars and shock absorption all enhance a boot’s physical comfort. Airflow aids comfort by keeping your feet from sweating too much, which creates bacteria and can result in developing foot fungus or other unpleasantness.


Many modern boots come equipped with extra-cushioned insoles for additional support and comfort. If your ideal pair of casual boots is lacking in the insole department, consider upsizing by half a size and adding aftermarket insoles. Keeping your feet supported properly can help prevent fatigue and chronic foot pain.

What to look for in a quality men’s casual boot


Boots typically are made from some type of leather or synthetic alternative, including some vegan materials, but fabric and other textiles are becoming more common as well. The best boots are made with quality materials that are durable and weatherproof, constructed for longevity and built to prevent excessive wear and tear.


High-top boots usually are more secure and offer enhanced stability, while low- and ankle-cut boots provide a bit more flexibility. Mid-cut boots aim to strike a balance between the other two profiles. If you plan on wearing your casual boots in intemperate conditions, a higher profile is recommended, while lower profile boots are fitting for more mild environments.


Factors such as sole traction and inner construction can add or subtract from a boot’s usefulness. If you plan on wearing your casual boots in slick conditions or slippery situations, it’s crucial they have adequate traction on the outsoles. If your new boots have enhanced padding or lining, they may be well-suited for chilly weather, but if they are also well-ventilated, they may be appropriate for all seasons. Consider casual boots that offer versatility.

How much you can expect to spend on men’s casual boots

Men’s casual boots start around $40 a pair and range between $50-$200. High-end boots made with rare or premium materials may run more than $200.

Men’s casual boot FAQ

Where can you wear men’s casual boots?

A. The biggest appeal of casual boots is their versatility. You can wear them in many professional situations, including some offices as well as in social settings. If they are weatherproof, you can wear them in less-than-optimal conditions.

Do you need to break in men’s casual boots?

A. Most leather boots require a breaking-in period of between 20 and 100 hours of wear to reach optimal comfort. If your casual boots are made from a more pliable material, the break-in period is considerably shorter.

What’s the best men’s casual boot to buy?

Top men’s casual boot

Timberland Men's Davis Square Chukka Boots

Timberland Men’s Davis Square Chukka Boots

What you need to know: From one of the most popular and trusted brands, this pair of Timberlands stands out among its classic fare with its unique look.

What you’ll love: These Chukka-style boots blend the stability of boots with a fashion sense usually reserved for collectible sneakers.

What you should consider: These casual boots run a little large.

Where to buy: Sold by Macy’s

Top men’s casual boot for the money

Bruno Marc Men's Motorcycle Boots

Bruno Marc Men’s Motorcycle Boots

What you need to know: These boots offer comfort and style without a high price tag.

What you’ll love: Vegan leather and a faux-fur interior provide the same quality construction as traditional boots, and the lace and zipper combo make them easy to slip on and off.

What you should consider: These biker boots run large.

Where to buy: Sold by Amazon

Worth checking out

Dr. Martens Unisex Crazy Horse Boots

Dr. Martens Unisex Crazy Horse Boots

What you need to know: The classic Dr. Martens flagship boot gets a material overhaul with Crazy Horse leather that improves with wear and age.

What you’ll love: The Crazy Horse leather is much more pliable than classic leather, making breaking-in less painful, and the bonded and cushioned soles offer day-long comfort.

What you should consider: Docs are not available in half sizes, so round up to the next full size.

Where to buy: Sold by Amazon


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Matt Fleming writes for BestReviews. BestReviews has helped millions of consumers simplify their purchasing decisions, saving them time and money.


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