Men’s Boots

Men’s boots come in a variety of styles including Chukka, Chelsea Boots, cowboy boots, and cap toe dress boots. And at Upscale Menswear, we sell a number of different luxury boot materials including alligator, calf, and ostrich skin boots as well as more traditional stylish leather and suede boots. Continue reading to find the right boot for your shoe collection.

Boot Styles for Men

Chukka Boot Characteristics

The chukka is a semi-casual style boot that sits on the lower part of your ankle and is made of three pieces of leather, finished off with three or four eyelets for boot laces. The chukka is very similar to the WWII-era desert boot made famous by the British Army and Clarke’s shoe store. Chukkas usually are made from suede or leather, although Belvedere do sell some chukka style boots in more exotic leathers. This type of boot is best worn with knitwear and chinos, although they are versatile enough to pair well with almost any outfit.

Chelsea Boot Characteristics

The Chelsea boot has exploded in popularity over the past couple of years, largely due to celebrities like Kanye West and Lebron James. They are simple slip-on boot with an elastic panel on the side that is ankle-high. The predominant material used for chelsea boots is leather, although you will occasionally come across suede versions of the boot. Much like the chukka, these boots will pair with everything from a suit to an oversized sweater.

Cowboy Boot Characteristics

Once seen as a massive fashion faux pas, the cowboy boot—or Western boot—has started to eek it’s way back into both men’s and women’s fashion. These boots are known for their ornate patterns that are emblazoned on them but Western boots can provide more than just a piece of artwork for your feet. The shin-high boot will add height to even the shortest of people (probably the main reason why the boot has been popular with actors and presidents over the years.) Western boots are begging to be showed off so it makes sense to have a pair that is made from a unique material like alligator, lizard, ostrich, or stingray.

Cap Toe Dress Boot Characteristics

The cap toe is a classic style of dress boot that has a rounded toe much like it’s flat-footed brother, the Oxford shoe. This piece of footwear demands to be worn with more formal clothing like a three-piece suit or a shirt and tie combo. However, a number of less formal cap toe boots have been released that mirror the style of Timberland boots. The less formal versions of this ankle-high boot are best paired with cargo pants or jeans and a casual block print tee.

Harness Boot Characteristics

The harness boot is similar to the cap toe and oxford-style boot, however, instead of laces, the footwear is secured with buckles or fasteners. Usually made from leather, these boots pair well with a suit and can make a good, stylish motorcycle boot in a pinch because it should come above the ankle and allow the foot to be well supported.

1–50 of 1304 items
1–50 of 1304 items