Best Boots For Men – Ultimate Stylish Leather Boot Buying Guide (Updated 2023)


boot in puddle

According to a study conducted by GQ Magazine:

‘76% of women think that casual boots are the sexiest shoes a man can wear on a first date.’

Which is all well and good – but that doesn’t mean a guy can just throw any pair of boots on and instantly look incredible. If it were that easy, we’d all be celebrating, gents.

The tricky part of wearing boots is knowing when and where they are appropriate:

  • Do you wear them with a suit?
  • Are there any jeans to avoid when wearing boots?
  • Can you wear boots with shorts?
  • What style is best for which season?

It can get confusing.

Don’t worry, gents – I’ve got you covered. Sit back, relax, and take note – in today’s article, I’m breaking out everything you need to know about buying a pair of A1 men’s boots.

We’ll be covering:

  1. What Makes A Good Quality Boot?
  2. The History Of Men’s Leather Boots
  3. How Do You Style Men’s Boots?
  4. What Are The Best Styles Of Leather Boots For Men?

Best Boots For Men – How To Identify Quality?

quality men's boots on the brick

To truly discover what makes a good boot great, we need to break down the features of construction into 4 key categories:

  1. Sole
  2. Welt
  3. Materials
  4. Style

The reason these 4 key aspects of a boot are so important to quality is simple: if a bootmaker cuts corners on any one of these, his boot can go from A1 to awful in the blink of an eye.

Top quality footwear is a very delicate balancing act – if one piece of the puzzle fails, the rest will come crumbling down. Let me give you an example:

Even if a boot has a sturdy leather sole, an upper made from solid, high-grade leather, AND has been designed to match the most stylish boots on the market – it will STILL fail if the welt isn’t up to standard.

As such, as a buyer of boots, you need to know how to identify quality in all of these different aspects of boot construction.

What Makes A Good Boot Sole?

sold men boot sole

It’s a fact – the sole of a boot is just as important as the material the boot is made from.

Why? It’s simple – the shoe’s sole is the part that will take the most beating on a day to day basis.

Typically, leather or a synthetic material like rubber will be used to make a shoe’s sole. Both of these have their advantages and disadvantages – it’s really up to you to decide which style of the sole will best suit your own personal needs.

boot construction inforgraphic

Starting with the leather sole, the key advantages of this style are:

  • The comfort of a sole that will adapt to the way you walk.
  • The breathability that a leather sole offers is essential when considering the health of your feet.
  • A heightened elegance in appearance. Leather soles both look and feel classy to wear!
  • The fact that leather soles can be easier to re-sole than plastic or rubber soles.
  • Sustainability in the sense that a natural material should last a long time and can be replaced.
  • The variety offered by leather means that not all leather soles are the same as one another.

However, with all advantages come disadvantages. Leather soles are no different, with their disadvantages being:

  • Their slippery surface – new leather soles are smooth, meaning you can easily slip and slide. Note: Some leather-soled shoes are Butyl-Treated: Butyl is a chemical used in making rubber, which also adds stickiness to the shoe and improves grip.
  • A lack of durability – rubber is harder wearing than leather. It’s a fact, gents.
  • A lack of water resistance – unlike rubber soles, they do not have a waterproof barrier between your foot and the ground.
  • Lack of cushioning – Leather is nice and soft and offers some cushioning. However, natural materials aren’t thick, so the space between the ground and your foot is decreased when wearing leather soles.
thursday boots black zipper boot

The opposite of a leather sole is one that is made of synthetic materials like rubber. These have their own advantages:

  • A greater range of different qualities when compared to leather.
  • The ability to offer a more lightweight feel and higher levels of breathability.
  • Thanks to the ease of production, they’re also cheaper to purchase and thus cheaper to replace.
  • Unlike some leathers, rubber soles are washable and can be wiped clean without fear of chemical damage.

However, with this cheaper man-made design, there are also many disadvantages to synthetic soles:

  • A typically lower quality material means less longevity of use.
  • They can look ‘cheap’ in comparison to more expensive soles – devaluing your overall style.
  • Fabric soles are less likely to be waterproof and are certainly less durable than leather soles.
  • Faux leather, or PU leather, is not as durable as real leather. However, it will be more durable compared to bonded leather.

What’s The Best Welt For Boots?

For those not in the know, a boot’s ‘welt’ is where the outsole attaches to the rest of the boot. All boots have a welt – however, there are a few different constructions that a cordwainer can choose from when making footwear.

Goodyear Welt:  

A Goodyear welt is a strip of leather, rubber, or plastic that runs along a shoe outsole’s perimeter. The basic construction involves stitching to secure the welt to the upper and a strip of pre-formed canvas that runs all around the bottom.

goodyear welt

A boot that features a Goodyear Welt has many benefits. These include the ability to re-sole the shoe regularly, the molding nature of the cork filler (molds to the shape of your foot), and the increased ventilation allowing air into and out of your boot.

Goodyear Welts are relatively waterproof – but I wouldn’t go as far as to suggest swimming in them.

Storm Welt (Also called the Norwegian Welt)

The Storm Welt leverages a very similar construction to the Goodyear Welt. However, it utilizes a slightly different design that allows the welt to bend upwards and around the sole – allowing more of a seal to be created between the upper and midsole.

The main benefit of this is an enhancement in the design’s waterproofing. Again – would I suggest going for a swim in your boots? Absolutely not. However, a Storm Welted shoe could certainly handle a few deep puddles without much trouble.

Blake Stitch:

A Blake Stitch is a welt that utilizes the “single stitch” method.

blake stitch

Basically, the shoe’s upper is folded underneath the insole, and then stitching is applied with a single thread to connect the layers of the boot’s sole.

Typically, a Blake Stitch welt makes it harder to replace the boot’s sole when it wears out and becomes damaged. However, on the plus side, the lighter construction of a single stitch means a boot that utilizes it is far lighter and flexible in design. This makes the Blake Stitch ideal for slimmer boots intended to be worn in more formal settings.

A Glued Sole:

The simplest (and possibly least favorable) of welt designs in the glued sole.

Regarding durability, a glued sole is not as strong as a Goodyear Welt, Blake Stitch, or Storm welt. Due to the welt’s simplicity, it is cheap to manufacture and is therefore used on cheaper boots and shoes.

What’s more – a glued sole can not be replaced. If the sole of a glued boot is damaged, then the boot is a right-off. I would always recommend ensuring your boots feature a strong, high-quality welting method rather than the cheaper glued option for longevity’s sake.

Which Materials Make Up The Best Boots For Men?

As with any item of clothing, stylish boots for men should be made of top-quality materials. In the case of boots – that means sturdy, high-quality leather.

A good rule is to aim for the highest-grade leather that you can afford. The higher the grade, the pricier the boot – however, genuine leather should be considered a minimum.

For those unsure of what I mean by Leather Grades, here’s a quick breakdown of the different levels of quality leather:

  • Full-grain – thick and rugged leather that hasn’t been sanded down or buffed
  • Top-grain – leather with a split layer with imperfections buffed away
  • Genuine – leather that has had an artificial grain (or texture) applied to its surface
  • Bonded – a mixture of leather scraps bonded together with synthetic materials

Unless you really have to, I’d advise you never to opt for synthetic leather. Real leather is tougher and will last longer if properly cared for. Synthetic leather will also reduce your boot’s ability to breathe – trapping moisture between your foot and the surrounding boot.

It’s also vital to remember that any leather, regardless of quality or grade, requires quite specific care to ensure your boots‘ longevity. To get the most out of your leather boots, I would advise that you:

  • Clean your boots after every use.
  • Polish the leather every week.
  • Condition the leather every 10 days.
types of leather
Leather can also be divided into different ‘grades’, which help indicate durability and quality.

Doing this will make the leather last longer and stay strong. Remember that leather is skin! What happens to unmoisturized and uncared-for skin? It cracks and wrinkles, leaving an old and worn-out aesthetic. The same thing will happen to leather boots, gents – so keep up a regular ‘boot care’ routine just as you would a regular skincare routine.

Why Does Style Matter When Buying Best Boots For Men?

high quality men's boots

Guys, it doesn’t matter if your boots are the highest quality shoes in the world – if they’re ugly and lacking in style, then they just aren’t gonna make the cut.

I would advise you to avoid ‘fad’ styles and stick to the timeless classics to guarantee this. Patent Leather Cuban Heels might have looked great in the 70s, but they’re not exactly the sort of boot a man could wear with masculinity in the 21st century.

Instead – go for the tried and tested classics.

Military lace-ups or Chelsea boots are great timeless options. Both of these boots can be worn casually and dressed up and look just as stylish now as they did 20, 30, or even 40 years ago.

On a practical level, it’s also important that stylish boots can be worn all year round. After all, what’s the use in spending your hard-earned cash on boots that can only be worn during a few months of the year?

With that in mind, there are a few things you should try to avoid when buying a pair of stylish boots for men.

  • Fur-lined boots are great for colder weather but useless in the summer months. If a boot has fur lining the inside of the shoe, there’s no way that it can be worn in hot weather. Imagine the foot sweat, gents – no one wants their feet to stink on a first date.
  • Equally, thinner materials like suede won’t work in wet and cold weather.

My advice would be to opt for an evergreen boot – made from waterproof leather without any material lining the inside. A boot like this will be thin enough to wear in the summer while also protective enough to keep your feet warm and dry when the temperatures drop.

History Of Men’s Boots

Pre-Historic Men’s Boots

Who would have thought that we’d still be wearing clothes today that our ancestors were wearing over 10,000 years ago?

According to historians, the oldest known depiction of boots can be seen in a cave painting from Spain. After careful inspection – historians concluded that a man could be seen wearing boots of skin, like a prehistoric version of the modern leather boot.

Even cave dwellers understood the importance of wearing stylish boots for men!

16th -18th Century

painting of man in boots

Pre-history is fascinating but let’s be honest – the boots worn by those long-gone ancestors were likely very different to what we wear today as modern men.

So let’s look at a slightly more modern form of history.

Within the 16th Century, men wore thigh-high boots of brown leather. These high boots of soft, perfumed leather were worn to meet upper stocks and gradually evolved into the early seventeenth century’s cavalier boot style. 

Widely recognized as the first military boot, the high-legged cavalier boots were worn by soldiers and became one of the first examples of a regimental uniform within Europe.

As fashion developed, so did the purpose of the cavalier boot. For 18th Century higher-class gentlemen, the sport of riding became a popular pass-time, and the high cavalier boot developed into a softer and closer fitting “jockey” style boot designed to be worn on horseback. 

19th Century

Boots have been used for riding for hundreds of years – both in the military and in leisure sports.

As the years progressed, the boot was more popular than ever.

In the 19th Century, Beau Brummel (considered the first ‘Dandy’) was known to wear “top boots and buckskins”.

As fashion shifted, so did the shape and design of the boot. The Wellington Boot – developed by the Duke of Wellington in 1817 – dominated menswear in the first quarter of the nineteenth century. 

The Blucher style of the boot had the most recognizable impact on what would become the modern boot. The basic laced-front style that The Blucher adopted would prove to be popular in modified forms to this day and has served as the basis of the modern high-top sneaker, hiking boot, and combat boot.

However, it was not until the late 19th Century that boots reached the peak of their popularity. A desire for greater comfort and practicality in footwear for both men and women became apparent and was aided by technological advances like sewing machines and vulcanized rubber.

The Wellington’s popularity died out in Britain but managed to survive in the United States – as the main contributor to the cowboy boot’s development.

cowboy boots
The classic Cowboy Boot – badass and still relevant today.

Believed to have originated in Kansas – the Cowboy Boot is considered a combination of the Wellington and the Mexican vaqueros’ high heeled boots.

In the United States, the Hessian continued to be worn and can be seen in photographs of the outlaw “Billy the Kid” from the 1870s.

20th Century

modern boots style
A classic silhouette ideal for casual weekend-wear

In the first half of the 20th Century, boots returned to their functional role and were traditionally used within the military through 2 world wars. 

As 1950 hit,  boots then reemerged as an important element in ‘young fashion’. Trends arose within youth culture, and boots played a big role in self-expression. 

During this time, elastic side boots became trendy as modern versions of the nineteenth-century originals. However, to add a bit of 50’s flair, a higher heel and a pointed toe were added, worn with slim-fit trousers.

Sound familiar? They should – after all, these were the original Chelsea boots.

How Do You Style Men’s Boots?

boot formality scale

The versatility of many boot styles is what makes them great. But it’s important to consider the formality of your footwear in the same way you would when deciding between a pair of loafers or cap-toe Oxford shoes.

Different boots suit different events and environments and learning which to wear for different levels of formality is essential to dressing with style.

Can You Wear Boots With A Suit And Tie?

First and foremost – when wearing boots with a suit, avoid ‘black tie’ suits. Tuxedo and black tie events strictly call for formal shoes as boots look too casual for super formal events.

At the end of the day, gents – you will look plain weird wearing boots with a tux. Instead, avoid boots altogether and opt for black oxford shoes.

When wearing boots to work – ensure they are well polished and shiny. This will complement the clean-cut look of suit pants. After all, well-polished shoes look professional and demonstrate to your employer that you put effort into crafting an appropriate appearance for work.

chelsea boots and suit

As with any shoe – always ensure suit pants are the correct length. Ankle-swingers look ridiculous when wearing boots as they would when wearing shoes.

Bulky soles and thicker-looking boots will heavily contrast the tailored look of a suit. This is a bad thing – your outfit will look mismatched and your stylish boots for men won’t look all that stylish anymore!

As a good rule of thumb, always opt for leather when wearing boots with a suit. Suede boots are fine for everyday wear but are a bit too casual for a suit.

Do Boots Look Best With Smart-Casual Outfits?

For smart casual – boots best compliment a pair of plain dark jeans.

When wearing jeans with a blazer and shirt, boots will help balance the outfit, whereas trainers will make it look too informal.

Equally, you should never wear dress shoes with jeans as this will do the opposite and make your outfit too formal looking.  Boots provide a good alternative to this.

A good rule is that jeans should be straight/slim-straight cut when wearing boots. Baggy jeans look too informal for smart-casual events, whereas skinny jeans never look good on a man (ever!).

dress boots collage with smart casual outfit

Slimmer straight-cut jeans compliment boots as they have a similar cut to suit pants but look less formal.

A smart casual dress code can call for either leather or suede boots. Leather is a good option for black/grey jeans (this is simply because darker colors suit the leather’s shine). In contrast, Suede is good for blue jeans (mid-blue, not light blue) as suede is a ‘fresher’ looking material.

Finally, both leather and suede boots can be worn with chinos. This will give a more formal aesthetic over jeans as chinos are a kind of step-up in formality. When thinking of chinos, the best boots to wear are chukka boots due to their heightened formality.

Lace-ups are more suited to jeans as they give off a slightly more casual aesthetic.

Boots With Weekend-Casual Outfits

For the most part, lace-up boots are great weekend wear. They are robust and hard-wearing, which makes them great for the outdoors.

We all know what a weekend trip with the kids can be like – so if they get muddy, you’ll be glad to know it won’t ruin them. In fact, some people like the look of ‘worn’ boots that show a bit of wear and tear.

If adventuring solo or with the kids is your thing, lace-ups with a thicker sole should be your go-to boot.

The thicker soles will manage mud and harsh ground well and provide you with the necessary traction.  Typically, the laces travel all the way up the boot, which provides better security while on foot.

For the best style, pair your lace-up boots with lighter jeans for a great ‘country’ look.

In this instance, it’s best to opt for straight-leg jeans. A straight cut is still stylish without being too formal.

It’s also important to note that lighter color jeans are the least formal jean style (think light and washed-out blues).

Wearing lace-up boots with light jeans is a timeless look and is a great way to wear stylish boots for men.

What Are The Best Styles Of Leather Boots For Men?

As I’ve touched on before, when we think of boots, we can categorize them within one of the three formality indicators:

  1. Casual Boots – can be worn with jeans, chinos, and trousers.
  2. Business Casual – boots that are more suited to a relaxed working environment where a ‘business’ dress code isn’t required.
  3. Dress Boots – more appropriate in offices where a suit and tie are required.

Unfortunately, buying a pair of stylish boots for men that can adapt to all three levels of formality is impossible. As such, you guys must have a great understanding of lots of different styles so you can make a more informed decision when it comes to purchasing stylish boots for men.

Chelsea Boots

chelsea boots

Chelsea boots are close-fitting, ankle-high boots that were first popularized in the Victorian era. Today, they remain a stylish and practical choice for both men and women.

One of the most distinctive features of Chelsea boots is the elastic side panel. This allows the boot to be pulled on easily and also provides a snug, comfortable fit.

In addition, Chelsea boots often have a loop or tab of fabric on the back of the boot. This serves both aesthetic and functional purposes, as it allows the boot to be pulled on more easily and helps to keep the boot in place. As a result, Chelsea boots are both stylish and practical, making them a great choice for any outfit.


  • Leather.
  • Suede.
  • Faux Leather.


  • The leather is sturdy but not always suited to outdoor adventuring.
  • Suede will ruin when wet and will tarnish easily – make sure to waterproof!


  • Leather – Brown or Black.
  • Suede – Broad color pallet. Often features pastel colors for summer.

Wear with:

  • Chelsea boots are the best boot to wear with a suit.
    • Slimmer design is sleek and classy.
    • Easily shined and polished – no laces breaking up the leather.
    • Options for cap toe/wing-tip style to vary formality.
  • Chelsea boots can easily be dressed down.
    • Chelsea boots can be worn with jeans and chinos.
    • Can offer a ‘retro’ look when paired with rolled-up hems.
    • Option for suede to create an informal look – strictly for dry climates.

Derby Boots (Smooth & Cap Toe)

derby boots

Men’s lace derby boots are dress boots with laces up the front and an open lacing design. They are typically made from various materials, including leather, suede, and synthetic materials. Men’s lace derby boots can be dressed up or down and are an excellent option for styling with suits and chinos.

When it comes to choosing the right pair of men’s lace derby boots, there are a few things to keep in mind. First, consider the material. Leather and suede are classic choices that will always look sharp, but synthetic materials can be a great budget-friendly option.

Next, think about the style of boot you want. Typically, lace-up derby boots come in two forms – cap-toe and smooth toe.

A smooth toe boot will have a more streamlined look and feel, while a cap-toe boot will have an extra layer of leather over the toe box. Neither design is better than the other – it really comes down to personal preference and style.


  • Made from a variety of materials
  • Softer brushed leather or hardy, thicker leather
  • Often flat laced made of a soft leather


  • If made from softer leather, they can be weak.
  • Sturdy leather design Derby boots can last a lifetime with the proper care

Wear with:

  • Can be worn informally or formally.
    • Wear with jeans and a t-shirt at the weekend.
    • Wear with a business suit during the week.
  • Not suitable as black-tie occasion wear.
    • When wearing a tux, do not wear Derby boots.

Moccasin Boots

moccasin boots

Moccasin boots are a type of footwear with a long and storied history. These boots are typically made from deerskin or another soft leather, and the whole boot is constructed from a single piece of material.

This design gives moccasin boots a unique look, and it also makes them extremely comfortable to wear.

In addition, moccasin boots often feature a vamp, an extra piece of material covering the top of the foot. This helps to protect the foot from the elements and keeps the boot from slipping off.

Whether you’re looking for a stylish footwear option or a comfortable pair of boots to wear around the house, moccasin boots are an excellent choice.


  • Softer brushed leather.
  • Less commonly – regular leather.


  • Softer leather can be weak.
  • Easily tarnished.
  • They have more of a fabric feel than a sturdy leather feel.


  • Traditionally tan color.
  • Moccasins are commonly colored in earth tones.

Wear with:

  • They should only be worn informally.
    • Wear with jeans and a t-shirt.
    • Suited to weekend day outfits.
  • Not suitable as occasion wear.
    • Avoid chinos – too formal for the moccasin.
    • Moccasins do not look good with a suit.
    • Equally, they do not look good in smart casual settings.

Chukka Boots

chukka boots

Chukka boots have been around for centuries, and they’re still going strong today. These ankle-high leather boots are a timeless classic, and they’re perfect for everything from a casual day out to a night on the town.

Chukkas usually feature leather or rubber soles, and they typically have two or three pairs of eyelets for lacing up.

The name “chukka” possibly comes from polo, where a chukka is a period of play. But “chukka boot” also refers to a form of desert boots originally worn by British soldiers in the Western Desert Campaign of World War II.

So whether you’re looking for a stylish footwear option or a practical pair of boots, chukkas are worth considering.


  • The Chukka boot has an ‘outdoors’ design.
  • Not a hiking boot as it simply isn’t durable enough.
  • Will withstand some rougher terrains if cared for well.


  • Chukka boots come in most standard leather colors.
  • However, Suede Chukka boots offer a wider range of colors.

Wear with

  • Doesn’t look out of place in a relaxed office environment.
  • Chukka boots suit both jeans and chinos.
  • Opt for jeans, shirts, and blazers for smart-casual environments.
  • Pairs well with jeans and a t-shirt/jumper at the weekend.
  • Never wear with a suit and definitely never a tux.

Double Monk Strap Boots

shoes every man should own double monk strap boots

The double monk strap boot is a stylish option for those who want the formality of a lace-up boot without the hassle of actually having to tie laces. This boot features two straps with buckles that securely fasten the boot to the foot.

The double monk strap boot is a versatile style that can be dressed up or down depending on the occasion. While they are not as formal as an Oxford shoe, they are more formal than a Chelsea boot, making them a perfect option for those who want to make a bit of a statement.

Whether you’re looking to add a touch of style to your work wardrobe or add a bit of edge to your weekend look, double monk strap boots are a great choice.


Wear with

  • A potential smart-casual boot.
    • A better option than wearing dress shoes (oxfords) with jeans
    • Bridges the gap between formal footwear and casual style
    • Stick to darker jeans – never light blue
  • Formal enough to wear with a suit
    • The best boots to wear in a business environment.
    • Double Monk boots are not appropriate for a tuxedo.

Wingtip (Brogue) Boots

wingtip boots

Wingtip boots are a stylish and practical footwear option for men who dress both formally and informally. The defining feature of this type of boot is the decorative perforations, or “broguing,” which can be found on the toe cap and along the sides of the boot.

While the origins of the wingtip boot are somewhat recounted, it is generally agreed that this style of footwear gained popularity in the early 20th century.

Today, wingtip boots are available in a variety of materials and colors, and they can be dressed up or down to suit any occasion. Whether you’re looking for a sophisticated footwear option for a formal event or a trendy way to add some extra personality to your everyday wardrobe, wingtip boots won’t steer you wrong.

Materials and color

  • Most commonly seen in brown leather.
  • Black and oxblood leather are other options.


  • Brogue boots were first utilized as outdoor footwear.
  • Often seen as hunting attire in Great Britain.
  • For a sturdier design, opt for Brogues with a thick sole.

Wear with

  • Appropriate with a suit (avoid black) and with casual wear.
  • Particularly good for darker jeans – avoid wearing lighter jeans.
  • Less formal than a monk strap boot, so better for smart casual.
  • A grey or navy suit – the more textured, the better.
  • Never a tux – wingtips just aren’t formal enough.

Combat Boots

wingtip boots

There are few things more iconic than a pair of combat boots. Whether you’re a soldier preparing for battle or a civilian headed to the mall, these tough, functional boots are up for the task.

While they may not be the most stylish choice for a night out on the town, they more than make up for it in terms of utility. Modern combat boots are incredibly lightweight and provide an excellent level of grip and stability, thanks to their tough outsoles and rugged construction.

Of course, no pair of combat boots is complete without a waterproof coating – perfect for those surprise puddles or stream crossings.

So next time you’re looking for footwear that can handle anything life throws your way, don’t forget the trusty old combat boot.


  • Made from hardy leather.
  • A high-shine leather isn’t necessary – it’s all about the boot’s durability, not the aesthetic.
  • Waterproofed leather is a necessity for modern combat boots.
  • A rubber sole combat boot is more typical than a leather sole.


  • Soldiers wear combat boots while in the field of battle.
  • Can cope with hiking, climbing, and running on any terrain.


  • They feature mostly earth tones and shades of black.
  • The camo effect is also popular due to the boots’ military heritage.

Wear With

  • It isn’t appropriate to wear combat boots to a special occasion.
  • However, it is appropriate to wear combat boots with jeans at the weekend.
  • Any color jeans in a straight/slim-straight cut are acceptable.

Hiking Boots

hiking boots

Hiking boots are an essential piece of gear for any hiker, especially those venturing on a long trip. They protect the feet from the elements and provide much-needed support for the ankles.

The boots are usually fairly stiff, which can be a blessing or a curse depending on the terrain. On rocky trails, the extra support is appreciated. But on a sandy beach hike, not so much.

Nonetheless, hiking boots are an essential piece of equipment for any serious hiker. So lace them up tight and hit the trail!


  • Trail shoes.
    • Made for hiking in dry climates, on well-established rocky paths. Suited for hiking during the day.
  • Trail hikers.
    • Ideal for wearing on muddy paths. They are considerably lighter than other hiking boots. However, they are still very sturdy and waterproof. These boots allow more ankle protection against the elements in comparison to trail shoes.
  • Mountain walking or hiking boots
    • Designed for hiking on mountains. They are powerful, have great durability, and leverage stiff soles to help support the feet and ankles on rough terrains.


  • Ideally, hiking shoes should be waterproof but also breathable.
  • Typically, the soles of these boots will be shock absorbant to provide cushioning for the feet.
  • The insole of hiking boots should mold to the shape of the wearer’s foot over time.


  • They can come in an array of colors.
  • Usually found in earth tones with an accent brighter color for visibility – sometimes featuring high visibility strips.

Wear With

  • These boots serve one purpose – to wear with hiking gear.
  • Consequently, I would advise that you do not wear these shoes with any other outfit – they are hideous shoes.

Wellington Boots

wellington boots

The Wellington boot was originally a type of leather boot. They were first popularized by Arthur Wellesley, the 1st Duke of Wellington.

The “Wellington” boot became a common example of practical footwear for the middle class in the early 19th century. However, in more modern times, the name has come to mean a waterproof boot made of rubber.

Wellington Boots are great protection against mud and water that might ruin clothing. So, next time you find yourself up to your knees in mud, remember the Duke of Wellington and his iconic boots. And maybe even thank him for helping to keep your clothes clean.


  • Traditionally made of hard-wearing leather in the 19th century.
  • Modern Wellington boots utilize a rubber design.


  • These boots are not at all formal.
  • Instead, Wellington boots suit extremely muddy conditions.
  • Not a fashion item – they are technical shoes.


  • These shoes are solid as their rubber construction is very hard-wearing.
  • Easily wiped clean and require little maintenance.
  • All rubber design makes them cheap but strong.


  • Found in any color.
  • All rubber design makes printing patterns on the boot easy for manufacturers.
  • There are no limitations to the colors and designs available.

Wear With

  • Any outfit where you don’t want to get your clothes wet and dirty.
  • They can be a good way of commuting in bad weather.
  • Just make sure to put formal boots on when at work!

In 2022 it’s easier than ever to buy an awesome pair of stylish boots for men. However, it’s important that you consider how you want to wear your boots before you buy them.

Every boot has a different purpose and a different set of styling rules to follow.

As such, knowing the specifics of men’s style when it comes to stylish boots for men is important.

Moreover, understanding when and how to wear particular boot designs will help to set you apart from other men and truly present you as a classy and well-dressed individual.

Just ensure that whatever you wear on your feet is both timeless and well-made so you can make the most out of the footwear you spend your hard-earned cash on.



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