Essential Guide to Men’s Boots

From Chelseas to Jodhpurs to

Written by Janet Hu

[Feature Image by Articles of
Pretty much every guy can rock
sneakers. And most men own a pair of dress shoes. Boots, however, are a heavily
underutilized form of footwear, and we think it’s because not many people know
where to start. That’s a shame, since men’s boots come in such a wonderful
range of designs, heights, materials, etc.
Take the quiz: What shoes
should you wear with your outfit?
In this essential guide, we’re
outlining the different types of men’s boots and giving some pointers on how
and when to wear them:
Men’s Boots: Chelsea Boot

men's boots cheslea boots

Height: Ankle

Laces or Pull-on: Pull-on
Style: These close-fitting
boots have an elastic side panel, and they are typically made of suede. Men and
women first wore Chelsea boots in the 1800s Victorian era. Then in the ’60s,
these boots made a re-emergence in British mod fashion when they became the
Beatles’ footwear of choice.
men's boots chelsea boots
How to wear it: The Chelsea
boot is semi-casual but trendy. Wear them with dark jeans and a blazer, sports
coat, or leather jacket.

Men’s Boots: Cap Toe Boot

men's boots cap toe boot

Height: Ankle

Laces or Pull-on: Laces

Style: Cap toe boots feature a
straight-seamed cap over the toes. These leather boots are considered more
formal and can be worn with dress slacks, chinos, nice jeans, and blazers.
men's boots cap toe boots

How to wear it: You can wear
cap toe boots with a winter suit and overcoat. Think: swank Sherlock Holmes.
Men’s Boots: Wingtip Boot

men's boots wingtip boot

Height: Ankle

Laces or Pull-on: Laces

Style: These low-heeled
leather boots are similar in style to cap toe boots. Instead of a straight seam
across the toes, though, wingtips feature a “W” shaped cap that extends toward
the heel. Wingtip boots have decorative perforations along the seams.
Originally called “brogue shoes,” wingtips used to be considered a strong
outdoor shoe, made from untanned leather. They’re now often worn in offices,
though still considered more casual than cap toe boot shoes.
men's boots wingtip boots
How to wear it: Wingtip boots
are semi-formal. You can wear them with a flannel suit or with dark jeans, a
collared shirt, and a sweater.

Men’s Boots: Desert Boot

men's boots desert boots

Height: Ankle

Laces or Pull-on: Laces

Style: These boots originated
in the ’50s as combat footwear worn by British soldiers in WWII. They feature
fewer eyelets than the average lace-up boot, making them easier to slip on and
off. Now, desert boots are often made of tanned leather or suede, and they
typically have crepe soles, which are soles made of latex and rubber. These
boots exist in the territory between formalwear and combat, and they are
signature to rogue style stars like legend Steve McQueen.
Desert boots are a type of
Chukka boot. The Chukka style is any ankle-high boot with a low number of
men's boots desert boots
How to wear it: Desert boots
are part of your “likes artisan beer” and “hipster variety.” Wear them with a
pair of nice, rolled pants.
Men’s Boots: Jodhpur Boot

men's boots jodhpur boots

Height: Ankle

Laces or Pull-on: Pull-on

Style: This is an ankle-length
riding boot with a rounded toe and low heel. The Jodhpur boot’s straps are a
defining characteristic. They attach to the vamp and can be fastened with a
buckle. These boots originated in India during the ’20s and were worn by local
polo riders. Then in 1927, Saks Fifth Avenue began selling these boots as
fashion wear in the West. Vogue once wrote that Jodphur boots should be worn
with a swagger stick and canary string gloves.
men's boots jodhpur boots

How to wear it: Jodhpur boots
are considered dressy, though not exactly formal. They’re a little exotic and
ornate. Wear them with a trendy blazer or cool leather jacket.
Men’s Boots: Riding Boot

men's boots riding boot

Height: Knee

Laces or Pull-on: Pull-on

Style: Riding boots come up to
the knee, and they are often made of patent, or shiny, leather. These boots are
for dressage, formal fox hunting, and show jumping. Tall boots once protected
riders’ legs from the saddle. That is, until Jodhpur riding pants with baggy
thighs came along, and ankle Jodhpur boots became the new riding boot.
men's boot riding boot

How to wear it: We’re going to
be honest: this is not an easy one to pull off. But the image above is a good
example of how you can dress down an otherwise very noticeable boot. Wear
riding boots with a collared shirt or blazer and some chinos.

Men’s Boot: Harness or
Motorcycle Boot

men's boots motorcycle boots

Height: High-Ankle to Mid-Calf

Laces or Pull-on: Pull-on

Style: These boots made of
thick, heavy leather protect motorcycle riders from exhaust pipes and engine
heat. They have a low heel and unadjustable straps closed with metal rings.
Harness boots will sometimes include a built-in steel toe cap and metal shank
in the heel to protect riders from injury.
men's boots harness boots
How to wear it: Harness boots
have an alternative and dark aesthetic. That’s why characters from The Vampire
Diaries would be sporting them. If you’re looking to add a heavy-duty or metal
edge to your look, wear harness boots with dark colored clothing. You can also
opt for brown boots instead of black, for a less intense look.

Men’s Boot: Cowboy Boot

men's boots cowboy boots

Height: Mid-Calf

Laces or Pull-on: Pull-on

Style: These boots, typically
made from cowhide, have a low heel and a rounded or pointed toe. They are often
decorated with ornate top-stitching or geometric cutouts and have an
under-sling heel–that is, a heel that curves inward. As the name suggests,
these boots were originally worn by American cattle ranchers in the 1860s. Some
cowboys wanted nicer boots to wear into town and thus came the ornate designs.
Today, some cowboy boots are even made of exotic alligator, snake, or eel skin.
men’s boots cowboy boots
How to wear it: Wearing cowboy
boots with anything but denim would be almost sacrilegious. Keep your look
casual and rugged. Wear a loose-fit collared shirt, maybe even a Western-style
button down, to pull off the country rustic aesthetic.
Men’s Boot: Workwear Boot
men’s boots workwear boots
Red Wing
Height: Ankle
Laces or Pull-on: Laces
Style: Workwear boots have
thick, water-resistant material and rubber soles. They have a chunkier,
sturdier look. Originally intended to protect workers from chemical substances
and water, snow or mud, workwear boots are perfect for hiking. These boots also
became fashion staples in hip-hop and punk scenes with popular brands like Doc
Martens and Timberlands.
Actual safety boots may
feature a steel cap over the toe to protect wearers from debris-related injury.
men’s boots workwear boots
Blue Collar Prep
How to wear it: Workwear is at
the intersection of street, grunge, and trendy. You can pair workwear boots
with light denim and a long overcoat, Kanye style.
Looking forward to your new
sartorial adventures. Which boot style would you try first? Let us know in the
Take the quiz: What shoes
should you wear with your outfit?

Kayode Ojo
Kayode Emmanuel Ojo is the Co-Founder and Managing Director at SHEFFA Limited. He is presently studying Computer Science at the National Open University, Victoria Island, Lagos.