Best Boots For Men | Boots Outfits, Brands and Styles

Let’s face facts: when the weather gets cold, your little piggies become dangerously exposed. Mesh sneakers let in freezing air, canvas shoes become sponges in snow, and anything low top spells doom for your ankles. To top it all off: when your body cools, your nervous system draws blood away from extremities to keep your heart and lungs at optimal warmth. Literally and figuratively, things aren’t looking too hot for your feet. 

Thankfully, this isn’t humanity’s first winter. Since prehistoric times, a simple footwear formula has fought off ice and wind: wrap foot in leather, make high-top, repeat. While we’ve added all sorts of stylish and functional variation over the years, both the formula and its output have remained about the same. Take it from the cavemen – if you’re looking for rugged, rakish, winter-proof footwear, look no further than boots.

Table of contents

Outfits Featuring Boots

There are a ton of different variations in boots, which means the ways you can style boots are pretty wide and varied. Generally though, you want to avoid wearing boots with shorts, and when wearing boots you want the rest of your outfit to also be on the rugged side. With the following inspiration outfits, you’ll have a great idea on how to style boots for men.

13 Best Boot Brands

Top Pick
Red Wing Heritage

Red Wing Heritage has been sporting americana style work boots, like the Iron Ranger, in Europe and Asia since the 70’s. Today Red Wing Heritage designs shoes that outlast fleeting trends, shoes they proudly dub “out of style since 1905” for those who aren’t afraid to swim against the current.

velasca boots

If you appreciate Italian craftsmenship, detail oriented design and a relentless pursuit of timeless style, you'll love Velasca. Their dark brown laced boots is our favorite boot in their collection. The blake construction guarantees lightness and flexibility while the Dockers rubber sole makes these shoes ideal for anything. Made from suede calf leather featuring a sleek and slim silhoutte - what else can you ask for in a boot?

wolverine boots

Famous for their 1000 Mile Boot, Wolverine has been turning out top quality work boots for over 135 years. What initially began as small tannery in Rockford, MI soon became an American-dream-style success story when founder G.A. Krause opened his first large-scale manufacturing facility and brought electricity to Rockford in 1883. All these years later, Wolverine insists on a quality of craftsmanship that endures. On the topic, and in their own words, Wolverine explains: “We’re not good because we’re old, we’re old because we stayed good.”

chippewa boots

Chippewa boots were engineered with an emphasis on reliability, authenticity, and most importantly, safety. Boasting electric shock protection, insulation, safety toe technology, and puncture-resistant features, these boots are designed for the most rugged jobs out there. Chippewa boots draw inspiration from the men who built our cities from the ground up, for those who are ready to step out and tackle the next big project.

blundstone crazy horse boots

Australian-designed, blundstone boots are iconic for their comfort, durability, and heritage. They're the footwear you wear when you're not just going around town, but around the world. The #983 is one of our favorite boots from Blundstone thanks to its lightweight construction and sturdy protection. The comfortable under-foot padding means that you can hike all day long across rough terrain without your feet getting sore. The heavy duty zip allows for easy on and off, which is great for quick changes into the shoes before heading out the door to work.

Thursday Boot Co

Thursday Boot Co seeks to embrace the unexpected by providing adventurers with a boot that is comfortable, durable, versatile, and honestly priced. Their inspiration, of course, is drawn from the unofficial start to the weekend and the flexibility that this gray area brings. Thursday boots are suitable for the boardroom, the sidewalk, and most any outdoor adventure.


Thorogood is most well-known for their “job-fitted” boots. Customers are hard-working people who cut through the bs to get the job done, and Thorogood helps them get there faster with boots tailored to their individual needs. These are boots for linemen, carpenters, firefighters, military personnel, and anyone else who needs a little support and a whole lot of reliability out of their footwear throughout the day.

Nicks Handmade Boots

As approachable as the name would suggest, Nick’s Handmade Boots have been personally designed and assembled by a dedicated team of craftsmen in Spokane, WA for the past 50 years. That’s what sets Nick’s apart – they’re essentially made to order. But this friendly business understands the implied risk of ordering a handmade item you can’t try before you buy, which is why they accept returns and exchanges for any boot in new condition.


In 1982, Magnum released their first product under the Hi-Tec umbrella in response to a direct request by the FBI for a lightweight tactical boot – this was of course The Magnum Classic. In 1990 they launched a collection of tactical boots globally, and after separating from Hi-Tec in 2000, they began expanding their offerings to include blue-collar work boots and healthcare options. Today Magnum has collected two awards for “Best Innovation in Safety Footwear” from Satra PPE, and thanks to oversight by the Magnum Tactical Advisory Committee, has maintained recognition globally as the first choice for military, fire, industrial, and uniform personnel.


Known for their signature white midsole, aka “the white line”, HELM strives for comfort and confidence through intentional design and aesthetic versatility. This brand is a

self-proclaimed classic in the making – first emerging as a boot manufacturer from Austin, TX in 2009, HELM initially stood out for their all-white rubber sole. Now, HELM has adopted an additional layer of leather beneath this iconic white rubber substrate and is keen on driving the design as a key identifier that doubles as an integral support component. Their next mission is to continue a legacy of versatility, timelessness, and functionality that translates in the workshop and in the office.


Once designed for the French Legion, Palladium is now a boot for artists, activists, aviators, ravers, and explorers of all sorts. Breathing new life into their original Pampa design from 1949, the Pampa High Originale is a favorite of modern adventurers looking to follow in the footsteps of legends like Haroun Tazieff, who trekked to the center of volcanoes in Palladiums through the mid 20th century.


Perhaps one of the most recognizable names on this list, “Timberland” once referred to a waterproof boot released in 1973 by the Abington Shoe Company. After the success of this particular launch exceeded the expectations of the shoe company, the boot itself became the brand’s identifier and they resolved to adopt the name. Creators of the Timberland attribute its popularity to its unique yellow design, cutting-edge durability, and all-weather performance. Initially a shoe enjoyed by rugged work and outdoorsmen, this classic quickly became a streetwear favorite.

Dr. Martens

What began as a utility boot geared towards blue-collar labor took an unexpected turn in the 90’s when they were adopted by pioneering bands of grunge culture and took Britain by storm. By the end of the decade they had gained popularity overseas and became

nu-metal, emo, and festival-culture staples. Dr. Martens appealed to counter-culture because they were an accessible way for young people to express comradery. Today Dr. Martens are a mainstream and versatile staple in the fashion space. Their incredibly functional design and rich cultural roots make them a trend-defying addition to any closet.

Types of Boots For Men 

Cataloguing boot styles is like trying to make a list of everything: noble, yet ultimately fruitless. While a Master’s of Boot History would look nice on a wall in our office, no one should have to read a dissertation on footwear to nail their style.

With your busy schedule in mind, we’ve distilled the universe of boots into the 5 essential styles making an impact on fashion today.

Even better: the list below is ordered from most functional to purely fashionable, outlining exactly how each style will fit your needs. From the street to the runway, city to the country, these boots will keep you warm – and look great doing it.  

Work Boot

What you need when there’s a job to be done. Work boots are chunky, weather-proof, and built for function. The style is there, too – it’s just not the focus. Instead, work boots emphasize pure utility through features like treaded outsoles, waterproof liners, and insulated uppers. Whether snow or mud stands in the way, a modern work boot will keep what’s outside… well, outside.

But that’s not to say they can’t look good doing it. Thanks to societal trends towards casualwear and urbanization, work boots from brands like Timberland and Rothco have become fashion pieces in their own right.

Timberland’s “Wheat 6” Boot” has even achieved cultural icon status all its own, thanks to co-signs from musicians, fashion designers, and celebrities of all spades. Most importantly of all, it’s still trusted by the millions who rely on it. 

Are work boots as fashionable as their suede-and-crepe cousins? That’s for you to judge. One thing’s for certain: in 2 feet of snow, the best look is the one that’s warm and dry. 

Heritage Boot

Red Wing Iron Ranger

What you think of when you think of “boots.” Heritage-style boots are made to look like the utility boots of old, with varying degrees of modernity depending on the model. Typical features include leather soles, waxed laces, and “Goodyear” welting (a special method of attaching the boot’s upper to its sole). 

Think of heritage boots as the perfect compromise between fashion and function. While they may lack the durability of modern work boots, heritage boots are rugged enough for snow-choked sidewalks and arguably look better with heavy use.

Some shoemakers (Viberg, Red Wing Heritage, Wolverine) even still make boots by hand, insisting on the highest-quality craftsmanship for each and every pair. By reaching to the past, heritage boots have built a presence in our present. 

Dress Boot


What you wear on Casual Friday, but all the other days, too. Dress boots have much in common with heritage boots, yet are typically made in fashion-friendly materials and designed to mimic dress shoes from the ankle down. These formal-focused boots often feature exotic leathers, thin laces, and decorative broquing.

Dress boots are the footwear equivalent of “loosening your tie” – the high-top marks them as decidedly informal, yet with the right pants, most can pass for officewear in a pinch. In the heyday of the menswear trend, dress boots dominated.

From the streets of Milan to the New York subway, the world’s most stylish guys flocked to brands like Alden, Saint Crispin’s, and Allen Edmonds for their devotion to quality. While #menswear has come and gone, those same shoemakers continue to turn out gorgeous dress boots worthy of envy. 

Fair warning: dress boots don’t come cheap. However, for their versatility alone, good dress boots are well worth the investment. 

Chelsea Boot

Common Projects

What you wear to the office, the Kanye show, and everything in between. Chelsea boots are round-toe boots fitted with an elastic webbing instead of lacing, making them both easy to put on and distinctively fashionable.

While Chelseas can come in either suede or smooth leather, the typical pair includes a leather sole, rounded toebox, and minimal stitching. 

Although sacrificing the grip of laces may mean decreased usability, any worries about utility fade away the second you slip into a pair. Chelsea boots are built to provide a different kind of utility: the kind that quietly improves your everyday life.

For one, they’re effortlessly stylish. Chelseas pair with everything from ripped denim to Italian suiting, fitting both streetwear and formal styles with ease. For two, they’re easy to wear. You never know how much you hate tying your shoes until you never have to do it.

Finally, they’re available at every price point. From ASOS to Common Projects, there’s a pair of Chelsea boots out there that will fit your taste and your budget. 

If you live below the snowline, there’s no reason not to own a pair of Chelsea boots. If you live above it, get two pairs just to be safe. Your wardrobe will thank you. 

Avant Garde Boot

Rick Owens

What your best-dressed friend is excited you also know about. Avant garde boots are any boots that riff on typical styles to create something entirely new. There are few good ways to describe the typical avant garde boot, since the style as a whole is defined by being anything but typical.

Instead, go with your gut: if it features exaggerated proportions, unexpected materials, or a remixed entry system (read: zippers on zippers), it likely fits this category.

To be blunt, avant garde boots are hard to wear. Unless you have an entire wardrobe built to support them, boots from designers like Rick Owens, and Guidi will look out of place rather than really frickin’ cool.

Which is a shame, since with the right context (read: black on black) and outfit (read: layers on layers), avant garde boots look really frickin’ cool. It should be assumed that boots you need to build an entire outfit around aren’t really designed for function, but for clarity’s sake: don’t wear avant garde boots unless it’s 60 and sunny. 

For their price tag, unfamiliar styling, and lack of utility, most guys found avant garde boots completely inaccessible. However, if you have the confidence (and the capital) to pull them off, by all means go for it. The rest of the world will catch up. 

5 Best Boots For Men

The following boots are proven classics that are always going to be in style, have a quality company backing them, and most of all – they look amazing. This is our top 5 boots pick.