Maybe you live in an area subject to unpredictable weather like
rain and snow, or maybe you’ve heard about the rising men’s boot trend and want
to see what all the hype is about. Whatever your reasons are, if you’ve found
yourself here, chances are you have no idea where to begin when it comes to
buying a pair of boots.
Not to worry, we’re here to help. Before you set out on your
boot browsing adventure, take a moment to read our comprehensive guide to
buying men’s boots – we’ll
provide you with an overview of their history, our favorite styles, and how to
A Brief History of Men’s Boots
Before we get to the fun stuff, let’s start with a brief
history of this popular yet underused style of men’s footwear. While both men
and women wear boots nowadays, they, like many other common items, were
initially designed for men. Though boots have a long history that appears to
trace back to 15,000 BCE, we’ll start our grand history tour somewhere a little
bit closer, the fifteenth century.
In this time period, men of all classes were known to wear
boots, often composed of brown leather and were designed as knee-highs. A
century later, boots were still popular among men, as seen by the development
of different styles. Boots were heavily utilized for specialized activities
such as horseback riding, as they provided ample knee protection.
In the eighteenth century, boots were no longer an everyday
staple and were instead reserved laborers, soldiers, as well as avid hunters
and riders. Men’s boots and their place in everyday life began to fluctuate.
The nineteenth century saw the return of the boot as a fashion statement rather
than specialized equipment, albeit often reserved to those of higher status.
While men’s boots were still widespread in the early
twentieth century, they resumed a functional role rather than a fashionable one,
often reserved for the military and for sport. Men’s boots once again rose to
prominence in the middle of the century thanks to counterculture inspired by
films such as Rebel Without a Cause.
The 1970s saw an increase in unisex styles such as oxfords
and chukka boots. As we transitioned into the twenty-first century, boots once
again became less a part of men’s everyday wardrobe and often reserved for
inclement weather, activities such as hiking, or associated with punk musicians
and fans. But, as you’ve probably noticed, the tides always turn, and men’s
boots have experienced a resurgence.
Now that boots are once again commonplace among men, let’s
take a look at some of the trendiest styles available.
The Chelsea boot came to prominence in 1950s London and has
become one of the most versatile silhouettes of men’s footwear. These
close-fitting ankle-high boots feature a bold elastic side panel and have grown
to become a staple of high-end men’s footwear.
This laceless style can easily be dressed up or down for a
range of occasions. If you’re aiming for a more formal look, pair Chelsea boots
with a tailored suit for a smart, sophisticated effect. Some popular color
combinations include brown boots with a gray suit or brown with a navy or dark
blue suit, but the options are endless and can be customized to fit your style
For a casual look, the Chelsea boot works well with jeans
and a tee shirt. For an effortlessly cool look, top it off with a casual
jacket, or try flannel if you’re aiming for something a little more rugged. However
you wear them, we recommend sticking with pants that sit just above the top of
the boot. After all, these cool boots deserve to be shown off.
Colden Chelsea Boot comes in timeless black and brown shades and emanates vintage
rock-and-roll style with a slightly modern twist. Expertly crafted from the
finest antiqued leather and boasting a highly flexible sole for reduced foot
fatigue and easy movement, this classic Chelsea boot takes street style to an entirely
The chukka boot, or desert boot, is defined by an
ankle-length cut, a rounded toe, two or three eyelets, and is constructed from
two smooth, unlined pieces of leather. The perfect blend of elegant and casual,
the boots supposedly earned their peculiar name due to its resemblance to shoes
boots worn by polo players (a polo playing period is called a chukker, or chukka).
This style can be easily paired with nearly everything in
your closet, if you play your cards right. For an easy, casual look, wear them
with jeans and a solid or striped tee-shirt (a common theme as you’ll come to
notice, if you haven’t already). If you’re looking to dress them up a bit, chukkas
pair well with chinos and a classic shirt such as a polo or button-down.
If chukkas tickle your fancy, consider our Men’s
Kenton Chukka Boot, a fantastic go-to option destined to be a staple in
your footwear rotation. Designed with a leather welt for a hint of classic
style and an EVA outsole for flexibility and shock absorption for a confident
stride, this extremely versatile boot is sure to put your best foot forward.
Wingtips & More
Though the aforementioned styles are our personal favorites,
there’s no shortage of styles to choose from. Wingtip boots, such as our Men’s
Colden Wingtip Boot, are a descendant of the classic wingtip shoe defined
by perforated toe caps.
Heftier boots, such as our Men’s
Cold Springs Plus Chukka Boot, are usually constructed from full-grain
leather and are designed to provide increased grip and traction necessary for various
Your One-Stop Boot Shop
Men’s boots have come a long way yet still manage to prove
themselves as a timeless favorite for men and women alike. Whether you’re
aiming for a refined look or something a little more rugged, Rockport’s casual men’s boots and
dress boots collection features an impressive lineup of men’s boots in the
latest styles, so you’re sure to to find your perfect match.