Not Made Just for Walking: Men’s Fashion Boots

Key Points

  • Men’s fashion boots have evolved throughout the centuries to become a necessary footwear item for style and functionality.

  • Men’s boots need to be tried on in person for optimal fitting.

  • Men’s fashion boots come in several different styles.

Boots have existed since the age of The Flintstones and have been used for several different purposes. There are boots for work, recreation, and even war. There are boots for riding (horses, motorbikes), dancing, hiking, and some just for looking good on your feet. The last type on the list is referred to as men's fashion boots.

Wearing the right pair of stylish men's fashion boots has the potential for making you stand out among your peers.

Boots as a fashion statement certainly have a past, are a big part of the present, and are likely to play a major role in the future of men's fashion.

An Overview of Men's Fashion Boots  

In the beginning, boots were created to protect feet by covering the entire foot, the ankle, and even part of the lower leg. You can imagine an early man dropping a rock on his toe and thinking to himself, "A good piece of tough leather over my foot might have prevented a boo-boo." Sandals and everyday walking shoes were good for protecting the soles of the feet, but not much else.

While there are still boots performing that same age-old function, there are also many different styles to meet any man's daily needs and fashion sense.

Male fashion boots

A Brief History of Men’s Fashion Boots

Cave paintings in Northern Spain, dating back to 15,000 B.C., provide the first depiction of men — and women — wearing boots. Whether hunting wild game or gathering firewood and building stones, then and now the feet are protected.

As it always does, history marched on and boots became status symbols for the rich, famous, and powerful while most common folk walked barefoot.

In the 15th century, men from every class rocked tall boots made from brown leather. During the 16th century, men started wearing cavalier boots of soft material that could be folded downward.  Military boots came to the forefront in the 17th century.

Chelsea boots came into existence in 1837, when Queen Victoria commissioned J. Sparkes Hall to make a pair of riding boots without laces because she kept getting them caught in her stirrup. What the queen wants, the queen gets.

In the 1900s, people saw the rise of other popular boots such as the chukka, seven minutes of play in polo games, so named because polo players wore them.

How Men's Fashion Boots Should Fit

Getting the right shoe size is the most important part of choosing a boot. Every brand of boot has different sizing, so it’s important to try them on before buying. Pro tip: There’s even a good chance your regular shoe size isn't the same as your boot size.

Wearing a boot that’s too big or too small causes friction resulting in bunions, blisters, hammer toe, and irritation.

All boots do not stretch or can be broken in time, which is another reason to try them on at the store. Make sure the toe box isn’t too tight, the heel height is comfortable, and the boot’s arch feels good. Overlooking these components can lead to major foot issues down the road.

Types of Men's Fashion Boots

You can find many different styles of men's boots at any local shoe store or online marketplace. Those style options include:

Derby boots: Derby boots feature an open lacing system and an elongated or round toe. They have an upscale look but are usually worn for informal occasions. The Derby is more casual than the related Oxford boot. Nothing is stopping you from wearing these classy-looking boots with a blazer and slacks. Another outfit option is rocking a pair of jeans and a leather jacket depending on the style and your personal preferences.

A man wearing fashionable boots leans against wall

Chelsea boots: Chelsea boots are close-fitting, ankle-high boots with elastic panels on one or both sides. Other types of Chelsea boots feature a loop on the back of the boot or a tab of fabric. Look for a high-quality pair when you’re shopping because there are many knockoffs made with fake leather. These are great options that go well with just about anything

Work boots: Work boots are the most durable boots on this list and are built to last for decades. Work boots usually have a high-quality sole and often feature a steel or composite toe for additional protection. These are good to have on hand if you have a tough outdoor chore and want to protect your feet from a work-related accident. They’re also a great choice to wear for fishing, hunting, camping or other outdoor activity that might get your boots dirty.

Jodhpur boots: Jodhpur boots are a popular variation of the Chelsea boot, but feature a strap and buckle around the ankle. The Jodhpur boot is an upper-scale boot that is a great addition to any man’s closet. These boots go well with suits, chinos or even slacks. They can be worn year-round and can elevate your outfit to the next level when you’re having a night on the town. 

Balmoral boots: Balmoral boots are a fantastic dressy boot option for men. They feature a closed lace system and a low heel. They are named after the Royal Balmoral Castle in Scotland, which is owned by the British monarchy. These boots have been worn by the upper class for centuries and still carry a distinguished air about them. There are several different styles, including wingtips, cap toe, and plain Oxford. Balmoral boots look good with a blazer, jeans, chinos, or a sports coat, and can be worn year-round.

Chukka boots: Chukka boots are unlined ankle-high leather boots with open lacing and a round toe box. They have a vulcanized rubber sole, which is a process of hardening rubber for durable footwear. Chukka boots can be worn from spring through fall, but are not good for winter wear. They come in a variety of styles. These boots go great with chinos, but also look good with a nice suit. Be sure to invest in a good pair because the toe box can stretch and collapse with low-quality material.

Man wearing boots crouches down on bridge

Combat boots: Combat boots are a unique choice for men who are looking for something a little bit edgy. These boots are synonymous with the punk rock scene of the 1980s and the '90s and are a mainstay in modern men's footwear fashion. They slightly resemble work boots but have a cool-yet-rugged aura about them. Combat boots pair well with casual and formal wear while giving you a bold look.

Hiking boots: Hiking boots are another durable choice – especially for those who love the outdoors. A good quality hiking boot is water-resistant and built to weather almost any storm. These boots are constructed from a wide range of materials, including Gore Tex, composite, nylon, Merino wool, full-grain leather, etc. There are several styles of hiking boots, such as lightweight, heavyweight, low-tops, etc. 

Oxford boots: The Oxford boot is a more durable form of the classic Oxford shoe, which features a closed lacing system. Oxford shoes are commonly associated with formal wear and business spaces. The Oxford boot is a sophisticated choice for those who like to dress up but also prefer a more upscale boot option. This style looks best with a suit or formal wear. It can also be worn with a casual outfit. These boots are perfect for the fall and winter seasons.

How to Wear Boots?

There’s no wrong way to wear any boot, but here are a few loose guidelines to make your boot journey easier.

Start by choosing the type of boot you’d like to wear. Next, decide if you are wearing a casual outfit or something more formal. If you’re wearing something more upscale like an Oxford boot, choose a blazer, dress pants, or even a dinner jacket.

Black boots are somewhat neutral and can be paired well with jeans, joggers or even chinos. The same is true of brown boots. It’s hard to go wrong with any outfit chosen.

Don’t be afraid to go out on a limb and experiment with different outfit combinations, textures, tones, and patterns. Perhaps some distressed jeans with a nice button-up could go well with your brown boots.

Man wearing boots leans up against hot rod

Best Boots for Men

Here is a carefully curated list of the best boots for men in a wide range of styles.

The Henley leather Derby boots are a great choice for someone searching for something rugged and upscale. These boots are made in Italy and come with a round toe in addition to a lace-up vamp. They come in two shades of brown: cuoio or brown. Both shades complement a variety of outfits. They’ll run you $425. 

If you’re looking for a great Chelsea boot from a company you can trust, look no further than the R.M. Williams Comfort Craftsman Chelsea boot. R.M. Williams has been around since 1932 and is most well-known for their high-quality Chelsea boots. This pair is handcrafted in Australia by 80 hands, using only one piece of leather. These are constructed from yearling cowhide leather, which is durable and long-lasting. These are perfect for your closet if you want to embody the energy of a punk rocker or have a sophisticated look. These books will run you $539.

For a work boot, the Wolverine Floorhand steel toe is your best bet. Thanks to the full-grain leather uppers, you don’t have to worry about breaking these in. They provide maximum comfort with removable cushioned footbed molds and you have great grip with slip-resistant soles. These come in multiple colorways and with solid waterproofing, can survive in just about any indoor or outdoor conditions. These will run you $95.

Thursday Boot Company’s Rogue boot is the perfect Jodphur boot for just about any type of man. These sleek boots feature antimicrobial shock-absorbing insoles and cork-bed midsoles that form to your feet. They also have Goodyear welt construction for longevity and Weathersafe suede, which is a waterproof material built for any type of weather. These high-quality Jodphur boots will run you $199. 

The Beckett Simonon Elliot Balmoral boot can give you a more distinguished look along with a quality you can trust. These boots are constructed from full-grain calfskin leather, which is sourced from a gold-rated tannery in Italy. These sturdy yet comfortable boots will develop a beautiful patina with time while the Vachetta leather lining regulates the temperature of your feet. You can easily style these timeless boots with chinos, jeans, or even slacks, and stand out among your friends. These boots will run you $239.

Man wearing boots and holding backpack

The Clarks Bushacre 2 Chukka boot is a comfortable, stylish and affordable option for men looking to expand their footwear collection. These are similar to Clarks’ popular Desert boot but seem to have improved on the overall design. This Chukka boot features a vulcanized rubber sole, which is comfortable yet durable. These come in multiple colorways. The pull-up leather construction gives them a more rustic look due to the frequent appearance of creases. These boots will run you $100.

Nike’s SFB Field 2 Gore-Tex boots are a stylish yet classic take on the combat boot. The popular footwear company has produced a waterproof boot with full-grain leather. These are comfortable and durable with a polished shine, which will help you stand out.

These lightweight boots come with an aggressive tread pattern on the sole, which gives you optimal traction in any environment. These all-black boots will run you $190.

Salomon’s Quest 4d Gore-Tex leather hiking boots are a reliable choice for someone looking for a boot that’s functional yet cool. These chunky boots feature an all-terrain Contagrip, which gives you optimal grip across a range of outdoor surfaces. They also have a protective mudguard, a molded Ortholite sock liner insole for breathability, and comfortable cushioning. These boots will run you $230.

Bruno Marc’s Oxford dress ankle boots are an affordable yet stylish option for the Oxford boot department. These boots feature premium synthetic leather uppers, a durable rubber sole, and a side zipper so you can easily take the boot off. There’s a cushioned latex midsole for comfort as well as shock absorption. These boots come in multiple classic colors and will run you $56.99.

Man walks with hands full of shopping bags

Step It Up With Fashion Boots

Any man concerned with fashion should have an assortment of boots in their closet.

Boots have endured multiple aesthetic changes over the years to the point that there are several different styles — not just the "protect-my-toes" variety. It’s important to try your boots on in person so you can get the best possible fit and prevent any potential health-related issues.

It’s hard to make a mistake when it comes to styling your boots with certain clothes. You should try to step out of your comfort zone for the best results.

There is a plethora of boots on the market, but you now have a much better understanding of the different styles and recommendations to consider in your search for the boots that suit your taste.

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