20+ Types of Boots for Men: The Most Fashionable Styles


The Fashionisto


Updated January 25, 2024

Fashionables Types of Boots MenPin
Explore fashionable types of boots for men. Photo: iStock

There’s a unique charm and allure to a well-dressed man, and boots are one of those quintessential elements that define a man’s style. From the casual appeal of chukkas to the formal elegance of Chelsea boots, the footwear market is brimming with various types of boots.

Let’s explore fashionable men’s boots and how they can elevate your style quotient.

Fashionable Types of Boots

Boots are not just a utilitarian necessity; they are a fashion statement, a symbol of one’s personality. They are pivotal in defining your casual, formal, or adventurous style with the best boot brands.

Be it a pair of chunky snow boots for winter hikes or sleek ankle boots for a trendy look at the office, boots can make or break your outfit. Remember, the proper boots complement your attire, and the wrong one can ruin even the most stylish ensemble.

Casual Comfort

Chelsea Boots Men OutfitPin
Add Chelsea boots to your wardrobe arsenal for a stylish look. Photo: Deposit Photos

These boots balance style and comfort, are ideal for everyday wear, and pair well with casual and smart-casual outfits.

Ankle Boots: The Versatile Staple

Fashionable Types of Boots Men Johnston Murphy Lewis Side Zip BootPin
Step up your casual style with side zip leather boots like this pair from Johnston & Murphy. Photo: Nordstrom

Ankle boots are a versatile staple in any man’s wardrobe. They offer various styles and materials, making them suitable for almost any occasion.

Ankle boots, as their name suggests, are boots that reach your ankle. They come in various designs, from lace-ups to slip-ons, and can be formal and casual.

Styling Ankle Boots: The versatility of ankle boots means they can be worn with almost anything. Pair them with a suit for a chic office look, or wear them with jeans and a tee for a casual, everyday outfit.

Chelsea Boots: The Timeless Classic

Fashionable Types of Boots Men Thursday Boot Co Cavalier Chelsea BootsPin
Embrace a classic boot with a pair of fashionable Chelsea boots. Photo: Thursday Boot Co.

Chelsea boots are a timeless addition to your footwear collection. They have been in vogue since the Victorian era and have stayed relevant thanks to their simplicity and versatility.

Chelsea boots are ankle-length boots characterized by their elastic side panels and pull-tab on the back. They are typically made from leather or suede and have a clean, streamlined profile.

Styling Chelsea Boots: The beauty of Chelsea boots lies in their adaptability. You can pair them with formal trousers for a polished office look or jeans for a casual outing. They provide a subtle sophistication to your outfit without overpowering it.

Chukka Boots: The Everyday Essential

Fashionable Types of Boots Men Clarks Desert Chukka Boot Sand SuedePin
Clarks is synonymous with the chic Chukka boot. Photo: Nordstrom

Chukka boots, or desert boots, are the perfect everyday footwear. They are comfortable, stylish, and easy to wear, making them a must-have in every man’s wardrobe.

Chukka boots are ankle-length boots with two or three pairs of eyelets for lacing. They usually have a soft suede upper and a crepe rubber sole, although leather versions are also standard.

Styling Chukka Boots: Chukka boots are incredibly versatile. Pair them with khakis or chinos for a smart-casual look or with jeans for a more laid-back vibe. The key is to keep the rest of your outfit simple and let the boots shine.

Moc Toe Boots: The Blend of Comfort & Style

Fashionable Types of Boots Men Red Wing Shoes Classic MocPin
Red Wing is a standout brand with its Classic Moc boots. Photo: Red Wing

Moc toe boots are a fantastic blend of comfort and style. They are known for their unique design and versatility, making them popular among fashionable men.

Moc toe boots are characterized by the moccasin-like seam that runs around the top of the boot. They typically have a wedge sole and are available in various materials, from leather to suede.

Styling Moc Toe Boots: Moc toe boots are perfect for casual outings. Pair them with jeans and a flannel shirt for a laid-back look or with chinos and a button-down for a more refined ensemble.

Unique Styles

Fashionable Boots Men Motorcycle Boots TanPin
Channel your inner biker with motorcycle boots. Photo: FP

These boots each bring a unique style and functionality, ranging from the rebellious biker look to practical water resistance to the unique closure of monk strap boots.

Monk Strap Boots: A Sartorial Statement

Fashionable Types of Boots Monk Strap Herring Burntwood Rubber Soled BootsPin
Herring offers British-made luxury with its monk strap Burntwood boots. Photo: Herring

Monk Strap boots represent a unique fusion of tradition and modernity. Their distinctive buckle feature offers an alternative to more conventional laced boots and is a bold choice for the fashion-forward individual.

Monk Strap boots are characterized by their buckle and strap system instead of laces. They typically feature one, two, or sometimes even three straps, each fastening with its buckle.

These boots are made from high-quality leather or suede and offer a polished yet contemporary appeal.

Styling Monk Strap Boots: Monk Strap boots are a versatile addition to any wardrobe. Their unique design stands out in formal settings when paired with a suit, adding an edge to traditional formal wear. They can be worn with jeans or chinos for a more casual approach.

Motorcycle Boots: The Rebel’s Choice

Fashionable Types of Boots Men Harley Davidson Waterproof Riding BootsPin
Look no further than Harley Davidson for the quintessential waterproof motorcycle boots. Photo: Harley Davidson

Motorcycle boots are the epitome of rebel chic. They are rugged, stylish, and perfect for those who love the open road. Motorcycle boots are designed with bikers in mind.

They feature a low heel and high shaft and are made from high-grade leather to protect against the elements. They often have metal accents and buckles for an edgy touch.

Styling Motorcycle Boots: Motorcycle boots add a touch of rebellion to any outfit. Pair them with skinny jeans and a leather jacket for a rocker vibe or with ripped jeans and a graphic tee for a grunge look.

Equestrian Styles

Fashionable Boots Men Riding BootsPin
Explore equestrian-style boots for a bold statement. Photo: Shutterstock

These boots are associated with horse riding and Western styles, featuring higher shafts, sturdy materials, and heel designs suitable for riding.

Cowboy Boots: The Wild West Icon

Fashionable Types of Boots Cowboy Boot Moonshine Spirit Kelsey Western BootsPin
Complete your Western look with these Moonshine Spirit western boots. Photo: Boot Barn

Cowboy boots, the quintessential symbol of the Wild West, are renowned for their unique design and durability. Characterized by a high shaft, pointed toe, and distinctive angled heel, these boots are traditionally crafted from cowhide leather.

However, they can also be made using various exotic skins for a more diverse appeal. Among the brands that excel in creating these timeless pieces is Tecovas, known for their handmade craftsmanship and adherence to classic cowboy boot aesthetics.

Styling Cowboy Boots: Cowboy boots can be dressed up or down. Pair them with jeans and a checkered shirt for a country look, or wear them with a suit for a bold, modern approach to formal wear.

Jodhpur Boots: The Equestrian Elegance

Fashionable Types of Boots Men Carmina Jodhpur Dress BootsPin
Bring sleek elegance to your footwear with a pair of leather Jodhpur dress boots. Photo: Carmina

Jodhpur boots, originating from the Indian polo culture, bring a sense of equestrian elegance to your footwear collection. These are short, ankle-length boots with a strap-and-buckle closure wrapping around the boot.

The sleek design and polished finish give these boots their signature look.

Styling Jodhpur Boots: Jodhpur boots work well with a variety of outfits. Pair them with tailored trousers and a blazer for a sophisticated look, or match them with jeans and a polo shirt for a polished casual ensemble.

Paddock Boots: The Rider’s Pick

Fashionable Types of Boots Men Ariat Heritage IV Lace Paddock BootsPin
Lace up in these stylish leather Paddock boots. Photo: Dovers Saddlery

Paddock boots, widely popular among horse riders, offer comfort, functionality, and style. Paddock boots are ankle-length, featuring a robust toe cap for protection, a sturdy zipper or laces for a secure fit, and often a heel to prevent the foot from sliding through the stirrup.

Styling Paddock Boots: Though primarily a riding boot, paddocks can be integrated into daily fashion. Pair them with riding pants and a polo for an equestrian-themed outfit, or wear them with jeans and a light sweater for a stylish, casual look.

Riding Boots: Equestrian Elegance

Fashionable Types of Boots Men Ariat Heritage Contour Field Zip Tall Riding BootsPin
Nothing quite says equestrian like tall riding boots. Photo: Ariat

Riding boots, tracing their origins back to horse riding, bring a touch of equestrian elegance to a man’s wardrobe. They exude a classic charm, making them an ideal choice for those who value tradition and timeless style.

Riding boots are characterized by their tall, sturdy design, typically reaching up to the knee to protect the rider’s legs. They are traditionally made from high-quality leather and feature a low heel to prevent the foot from sliding through the stirrup.

Riding boots come in two main types: dress boots, which are more formal and feature a smoother finish, and field boots, which have a laced front for added flexibility.

Styling Riding Boots: While initially designed for horse riding, riding boots have found a place in mainstream fashion. They can be paired with various outfits, from tailored trousers and blazers to casual jeans and a sweater.

Although not typically used for formal occasions, their sophisticated design allows them to add a touch of refined style to an ensemble.

Rugged Functionality

Types of Boots RuggedPin
Add a rugged sensibility to your look with a pair of work boots. Photo: Shutterstock

These are tough for challenging conditions, often associated with specific occupations or activities requiring sturdy, durable footwear.

Combat Boots: For the Adventurous Spirit

Fashionable Types of Boots Explorer Combat Boots Thursday Boot CoPin
Ground your outfit with a strong statement courtesy of combat boots. Photo: Thursday Boot Co.

For those who prefer a more rugged, adventurous look, combat boots are the perfect choice. They are sturdy, durable, and exude a masculine charm.

Combat boots, as the name suggests, are inspired by military footwear. They are characterized by their high-top design, lace-up front, and heavy-duty soles.

They are typically made from durable materials like leather or canvas.

Styling Combat Boots: Combat boots can add an edgy touch to your outfit. Pair them with jeans, a leather jacket for a rocker look, cargo pants, and a flannel shirt for a grunge vibe.

Engineer Boots: The Road-ready Footwear

Types of Boots Men Chippewa Engineer BootsPin
Engineer boots make a distinct impression with their rounded toe and buckled strap. Photo: Boot Barn

Initially designed for railroad workers, engineer boots are popular for bikers and those looking for sturdy yet stylish boots. Engineer boots are characterized by their buckled strap, rounded toes, and durable construction, typically made from high-grade leather.

Styling Engineer Boots: These boots add an edge to your outfit. Pair them with jeans, a leather jacket for a biker-inspired look, cargo pants, and a casual tee for a robust, everyday ensemble.

Logger Boots: The Tough Terrain Tackle

Types of Boots Men Danner LoggerPin
The logger provides a protective workwear boot style. Photo: Danner

Logger boots are designed to tackle challenging terrains, providing safety and comfort for those in the logging industry. Logger boots are characterized by their high shaft, superior traction, and, most notably, their raised heel.

This unique design provides stability on uneven terrains and assists in climbing log ladders.

Styling Logger Boots: While these boots are primarily workwear, their rugged style can be fashionable. Pair them with heavy denim jeans and a flannel shirt for a rustic, outdoorsy look.

Work Boots: The Robust Companion

Types of Boots Men Timberland Pro Work BootsPin
Timberland makes its iconic work boot for on-the-clock hours and leisure. Photo: Work Boots

Work boots are constructed for durability and safety, designed to endure long hours of physical work. They are robust companions for those in heavy industries or intense physical jobs.

Work boots are easily recognized by their reinforced construction, often featuring steel toes and sturdy materials. Built to be tough, they’re not just for protection but also for comfort during prolonged wear.

Styling Work Boots: These boots are more about functionality than fashion, but that doesn’t mean they can’t be styled. Pair them with durable work jeans and a flannel or canvas shirt for a practical yet laid-back look.

Outdoor Adventure

Fashionable Boot Styles Men OutdoorsPin
Wear timeless styles like the rubber Wellington boot as you enjoy the great outdoors. Photo: Deposit Photos

These boots are designed with the great outdoors in mind, offering features like water resistance, insulation, and robust soles for traction.

Duck Boots: The All-Weather Friend

Types of Boots Men Sperry Waterproof Duck BootPin
Brace against the elements with Sperry’s waterproof duck boot. Photo: Sperry

Duck boots are an all-weather friend. They are designed to keep your feet dry and warm, making them a practical choice for weather conditions.

Duck boots are easily recognizable by their rubber lower section and leather upper. They feature a lace-up front and a thick sole for maximum traction.

Styling Duck Boots: Duck boots can be worn in any weather condition. Pair them with jeans and a parka for a rainy day, or wear them with joggers and a chunky sweater for a cozy winter look.

Hiking Boots: For the Outdoor Enthusiast

Types of Boots Men Hiking Boots MerrellPin
Embark on new trails with these Merrell hiking boots. Photo: Rei

Hiking boots are a must-have for the outdoor enthusiast. They are designed to withstand the rigors of the trail, offering durability, comfort, and protection.

Hiking boots are characterized by their rugged design, high-top construction, and durable materials. They often feature a padded collar, reinforced toe, and a lug sole for maximum traction.

Styling Hiking Boots: Hiking boots can be worn for outdoor adventures or as a fashion statement. Pair them with cargo pants and a flannel shirt for a hike, or wear them with jeans and a sweater for a rugged, urban look.

Wellington Rain Boots: The Practical Choice

Fashionable Types of Boots Men Barbour Wellington Boots Olive GreenPin
Barbour is one of the go-to brands for rubber Wellington boots. Photo: Barbour

Wellington rain boots are a practical choice for those in wet climates. They keep your feet dry during rainy days, ensuring comfort and style.

Rain boots are characterized by their waterproof material, typically rubber, and high shaft. They come in various colors and patterns, making them a fun addition to your rainy-day ensemble.

Styling Wellington Rain Boots: Rain boots can be paired with various outfits. Wear them with jeans and a raincoat for a practical, rainy-day look, or pair them with shorts and a t-shirt for a playful summer shower ensemble.

Snow Boots: For the Winter Warrior

Types of Boots Men Snow Boots Sorel Caribou BootPin
Prepare for a winter wonderland with Sorel’s Caribou snow boots. Photo: Sorel

Snow boots are the ultimate winter warriors. They are designed to keep your feet warm and dry in the harshest winters, making them a must-have for those in colder regions.

Snow boots are characterized by their high shaft, waterproof material, and insulation. They often have a rubber sole for maximum traction and a faux fur lining for added warmth.

Styling Snow Boots: Waterproof snow boots are a practical choice for winter. Pair them with thermal leggings and a puffer jacket for a cozy winter look. Remember, the key is to keep your feet warm and dry, so opt for boots with adequate insulation and waterproofing.

Formal Elegance

Fashionable Types of Boots Men Formal Cap ToePin
Modernize your formal wardrobe with the addition of smart leather boots. Photo: Deposit Photos

These boots are often crafted from high-quality materials and offer a sleek, polished look suitable for formal occasions or upscale casual events.

Balmoral Boots: Timeless & Regal

Fashionable Types of Boots Men BalmoralPin
Discover Carmina’s Balmoral boots for elevated formal footwear. Photo: Carmina

Balmoral boots blend timeless appeal and regal aesthetics, distinguishing them for formal and upscale casual occasions. Balmoral boots, also known as Bal boots, are characterized by their closed lacing system and a seam that runs along the length of the shoe, distinguishing the toe and vamp from the upper.

Often made from high-quality leather or suede, their sleek, polished appearance is accentuated by the absence of broguing or excessive detailing, aligning with their formal nature.

Styling Balmoral Boots: Given their refined look, they pair excellently with formal attire such as suits and tuxedos. They can be worn with tailored trousers and a blazer for less formal yet classy affairs. Their minimalistic design allows them to effortlessly complement a wide range of ensembles while adding a touch of royal sophistication.

Brogue Boots: The Decorative Detailing

Fashionable Types of Boots Men Beckett Simonon Nolan Brogue BootsPin
For formal footwear, brogue boots are easy shoes to complement a variety of looks. Photo: Beckett Simonon

Brogue boots, known for their decorative perforations or ‘broguing’ on the upper part of the boot, bring a classic touch to your wardrobe. Brogue boots stem from the traditional Irish shoe meant for outdoor wear.

The decorative perforations served a purpose: to allow water to drain when walking through wet terrain. Now, they’ve evolved into a style staple.

Styling Brogue Boots: These are versatile and range from semi-formal to casual. Pair them with a tweed suit for a classic look or with jeans and a chunky sweater for a more relaxed outfit.

Cap Toe Boots: The Sophisticated Touch

Fashionable Types of Boots Men Allen Edmonds Landon Cap Toe BootPin
Dress up your footwear with the cap-toe leather boot. Photo: Allen Edmonds

Cap-toe boots add a touch of sophistication and elegance to any outfit. They’re a classy choice for both formal and smart casual settings.

Cap-toe boots feature extra leather over the toe area, creating a ‘cap.’ They’re typically made from premium leather or suede and often have intricate detailing or broguing on the cap.

Styling Cap-Toe Boots: Cap-toe boots pair well with smart outfits. Wear them with a suit for a formal event or dark jeans and a blazer for a more relaxed, smart casual look.

Dress Boots: Elegance Meets Comfort

Types of Boots Men Dress Boots Jack in Tux TAFTPin
TAFT takes inspiration from the tuxedo for its Jack in Tux dress boot. Photo: TAFT

Dress boots are the epitome of sophistication and elegance. They perfectly blend the robustness of a boot with the grace of a dress shoe.

These boots are made from top-quality leather and often feature intricate detailing and a polished exterior. The main characteristic of a dress boot is its refined, sleek design, which aligns with formal attire.

From a distance, they might even pass as dress shoes. One significant differentiation is the boot’s length, which extends above the ankle, providing a unique touch to your ensemble.

Fashionable Type of Boots Men Cole Haan Dress Chelsea BootPin
Opt for a leather dress Chelsea boots for formal occasions. Photo: Macy’s

Among these, Chelsea dress boots differentiate themselves. They maintain the classic Chelsea style with elastic side panels and a pull-tab for easy wear but introduce elements of formal aesthetics.

Unlike regular Chelsea boots known for casual versatility, dress Chelsea boots embody sophistication with superior leather, refined detailing, and a polished finish, making them a fitting choice for formal settings.

Styling Dress Boots: Dress boots are incredibly versatile. Pair them with a sharp suit for a business meeting, or pair them with fitted jeans for a casual yet refined look. Remember, the key is to match the color of your boots with your belt for a cohesive look.

Wingtip Boots: Classic Meets Versatility

Fashionable Types of Boots Thursday Boot Co Wingtip BootsPin
Turn heads with elegant wingtip boots. Photo: Thursday Boot Co.

Wingtip boots offer a dynamic blend of classic design and modern versatility, making them a sought-after choice for formal and smart casual wear. Wingtip boots are characterized by their distinctive toe cap pattern, which spreads towards the sides of the boots in a shape reminiscent of wings, thus the name.

The design often includes perforations or ‘broguing’ along the ‘wings’ edges, adding to their classic appeal. These boots are typically made from quality leather or suede and balance traditional and contemporary styles.

Styling Wingtip Boots: Thanks to their distinctive design, Wingtip boots can add a bold statement to various outfits. They pair well with suits for a traditional formal look but also work great with jeans or chinos for a more relaxed yet still polished appearance.

Their detailed design makes them a standout choice for those seeking to add a touch of personality to their footwear collection.

The Ideal Boots

Boots are more than just footwear. They are a reflection of your personality, your style, and your lifestyle. Whether you’re a rugged outdoorsman, a stylish city dweller, or a laid-back casual guy, a pair of boots out there perfectly captures your essence.

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