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So step into the world of men’s boots and see how you can
incorporate this unexpected footwear into your everyday wardrobe.
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Table of Contents
1. Oxford Boots
2. Derby Boots
3. Chelsea Boots
4. Chukka Boots
5. Desert Boots
6. Jodhpur Boots
7. Monk Strap Boots
8. Moc Toe Boot
9. Engineer’s Boots
10. Cuban Heel Boots
11. Steel-Toe Boots
12. Combat Boots
13. Duck Boots
14. Hiking/Winter Boots
15. Cowboy Boots
16. Different Boot Styles
16.1. Plain Toe Boots
16.2. Cap Toe Boots
16.3. Brogue Boot Style
16.4. Wingtip Boot Style
Oxford Boots
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The Oxford dress shoe is very popular footwear for men; it’s a
classic choice for most suits, from formal to casual. Although the
dress boot version isn’t a commonly seen style, it can work just as
well with most suits.
Oxford boots are set apart from most other men’s types in the same
way the shoe is identifiable; Oxford’s have a closed lacing system.
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This means that the eyelet strip is sewn underneath the vamp so
that when you lace up your shoes, the two quarters are pulled
tightly together.
You can safely wear these boots with your best work suits, but don’t
try to pair them with formalwear.
Oxford boots are also a wonderful match with casual suit outfits;
they lend your clothing a somewhat dressier feel, but because they
are boots instead of dress shoes, they add an unexpected twist.
Derby Boots
Derby boots are similar to Oxford boots but have one significant
difference. Their lacing system is open versus the closed lacing of
Oxford’s dress boot.
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Derby boots are another solid choice if you’re looking for a dress
boot with a supportive high ankle.
Therefore, many men who don’t have strong ankles do well with a
firm leather boot.
Derbys are a popular boot style but are firmly casual. However, you
can dress them up to wear them with a suit.
Chelsea Boots
This style of men’s boots is incredibly popular, primarily because of
their versatility. You know this look; these are trendy ankle boots
with elastic sides on each ankle, running the height of the boot.
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They are easy to spot because they don’t have laces; instead, you
can quickly pull them on and off.
Chelsea boots have a very low profile and are super simple and
clean because of the lack of laces. They’re usually leather but are
frequently found in suede and can be smooth or textured.
The dressier Chelsea boots in dark leather are fine to wear with
most suits even for business settings.
But most Chelsea boots are wildly casual and trendy and are
commonly worn with jeans or other casual trousers.
Chukka Boots
Chukka boots have very low ankles and are easily recognizable
because they only have two or three eyelets.
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They have a slight heel and always feature open lacing. Most chukka
boots have thin soles of either leather or vulcanized rubber. They
are also characterized by their rounded toe box.
Because of their low profile, the chukka boot is suitable for year-
round use.
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of dress shoes.
Also, because they don’t have sturdy ankles, pick chukka boots with
high-quality construction.
The chukka boot is most popular in suede styles. If you opt for a
suede pair, remember that they will be most suited to casual
clothing.
They would work just fine for a smart-casual ensemble, with khakis
and a long-sleeve polo shirt, but not for any more formal outfits.
A leather pair of chukka boots work well with a casual suit, though.
Desert Boots
Desert boots are a variation of chukka boots. They have the same
design as a standard chukka but a different sole.
Desert boots’ soles’ are made from crepe rubber, which means they
are softer and easier on your body.
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Therefore, desert boots are good to wear to jobs that require a lot of
standing on your feet throughout the day. However, the soles aren’t
known for being durable, so they’ll quickly wear down on the
cement.
Desert boots are solidly casual. You can’t dress up this chukka, so
keep these boots for your less formal outfits. Wear them with very
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light khakis or grey chinos and a canvas jacket for a bit of a preppy
look.
Jodhpur Boots
This boot style is like a Chelsea boot, only with straps and a buckle at
the ankle in place of elastic. Just like the elastic of a Chelsea boot is
functional, so are the strap and buckle on the jodhpur boots.
You can tighten or loosen the boots as needed. The uppers of these
boots are one sleek and continuous smooth silhouette.
The strap and buckle at the ankle are often hidden in the hem of
your pants. А surprise waiting to be revealed when your ankle
moves.
Wear jodhpur boots the same way you would wear Chelsea boots.
They can be surprisingly dressy in dark leather.
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Thus, monk strap boots are similar to Jodhpur’s. The main difference
is where the ankle strap is sewn.
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Monk straps are very classy and versatile. They’re perfect when
paired with a suit, making your entire outfit energetic and refined.
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Most moc toe boots also have a wedge heel and a crepe rubber sole.
These are both a sure indication of a casual boot.
Because this is a rare boot style with a flat bottom and no heel,
some men like to use the moc toe boot as work boots.
Moc toe boots are less rugged than pure work boots, however. So,
while you can’t dress them up well, you can add them to some nice
outfits to create a unique, ruggedly preppy look.
They are most appropriate with jeans and a t-shirt, but if you wear
them with chinos and layers up top, you get a nice outdoorsy
effect.
Engineer’s Boots
If you’ve been searching for a fashionable workboot, here’s the real
deal. Engineer’s boots have few seams, so they are relatively sleek.
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The heels on these boots are one hundred percent for style; they
are fashionable and add tremendous flair and panache.
Play up the heel on your Cuban heel boots when choosing what to
wear with them.
Since these boots give you a little swagger to your walk, opt for
clothes that are a little more flamboyant than what you might wear
with most other men’s boots. They look stunning with slim-fit or
skinny pants.
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Wear these any place you want to embrace your inner rockstar.
They will be a perfect style for a concert, party, or a fun date night.
Steel-Toe Boots
Steel-toe boots are the ultimate work boot. You know these boots
will last a long time with the proper care.
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They are pure function over form. However, steel-toe work boots
have many different looks.
Some are all leather, while some have canvas construction. Some
men and women wear these boots to establish a super rugged style,
but this is only advisable in small doses.
Steel-toe work boots are cumbersome and heavy, and wearing them
for long periods when you don’t need to can damage your feet if
they don’t fit you perfectly.
As nice as the all-leather work boots can look, they are not at all
dressy. Though you won’t ever be able to pair these with a suit or
any office wear, they look great with chinos.
But, of course, jeans are never the wrong choice with these hard-
wearing boots.
Combat Boots
Yes, I’m talking about actual combat boots here as a fashion choice,
the same boots worn in the army.
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Combat boots have a very high ankle and feature a clunky rubber
sole and heel. Because they are such high boots, most have around
twelve pairs of eyelets. They’re traditionally black but come in
brown, too.
You may be surprised by how many outfits you can create around a
pair of combat boots. They look spectacular with a pair of cargo
pants, possibly because they are reminiscent of a military uniform.
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Because combat boots have a lot of heft, you don’t want your pants
to obscure them. Either cuff your pants to show off most of your
boot shaft, or be sure the hem of your pants ends well before the
top of your foot.
Duck Boots
Duck boots are perfect for rainy days and help you stay stylish while
keeping you dry.
You can easily recognize duck boots from their rubber bottom
portion and leather upper half. In addition, their rubber sole is ideal
for traction, preventing you from slipping on wet surfaces.
Although duck boots were initially designed to keep hunters’ feet dry
on rainy outings, you’ll find them well outside the hunting grounds.
You can wear them, too, anytime you want to showcase your best
outdoorsy style.
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Khakis and chinos complement these boot styles well; top off the
outfit by layering a pullover and a vest or light jacket.
If you are worried about keeping the hem of your pants dry, avoid
tucking them into your boot. Instead, roll them up to keep them out
of puddles.
Hiking/Winter Boots
This boot type is designed more with performance and comfort than
fashion.
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Hiking and winter boots types are made to help your feet, protecting
them against rough, slippery terrain and bad weather.
Most winter boots don’t add style to your outfit; they are designed
with snow in mind and little else. However, hiking boots are
sometimes a little more stylish, and you can wear them to enhance
your rugged approach to dressing for the day.
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For example, you can create a spectacular autumn outfit with wool
trousers, a medium-weight sweater, and hiking boots.
Cowboy Boots
You know the look of cowboy boots. These extend well past your
ankle and partway up your shin.
Still, you can pull them off and on without the help of elastics,
buckles, or even laces. Cowboy boots also have a fairly stacked heel.
Fortunately, you don’t need to be from the west to pull off this look.
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Although they usually pair best with dark, clean-cut, fresh jeans and
a dress shirt, some men successfully wear cowboy boots with a
suit.
So, consider a few things when choosing your boots. First, think
about your goal for your formality and what style of pants you
intend to wear. Also, remember that the more you embellish your
boots, the less dressy they are.
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They are the height of smart casual; you can dress them up with
chinos and a button-down dress shirt or style them with crisp
jeans and a simple sweater.
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Cap toe boots are defined by a seam across the boot’s toes. The
result is a cap over your toes, hence the name.
Cap toes are more casual than plain toe boots, but the detailing
adds more interest to your ensemble. Fortunately, cap toe boots go
well with most outfits.
For example, they work well with a casual suit but would not be
acceptable in most office spaces.
Instead, wear these boot styles with a blazer or other layers and a
pair of dress trousers.
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Boots that include this detailing are classy looking and quite
contemporary. In addition, they hold a lot of “personality”.
Although brogue boots look great with a business suit, they are not
acceptable in a conservative business setting.
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Wingtip boots are hip and styled in a contemporary manner but can
also have a very vintage feeling.
If your boots are shined and in good shape, they will perk up a
tweed suit or add serious style to your average pair of crisp, slim-fit
jeans.
Hi, I’m Alex, and I’ve studied and specialized in styling in Rome.
Through my writing, I want to help men dress well and learn
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