Whether you are out at a high-end event, going out for a day of fun with friends, or just chilling at home with your family, there is a boot to be had for every occasion!
However, it can be difficult to know exactly what style of boot to choose as there are so many different kinds out there, some of which are better suited for certain occasions than others.
With this in mind, we have compiled a comprehensive guide of sixteen of the absolute best boots that every guy should know about and have a pair of in their wardrobe.
We are going to take an in-depth look at each one of these boots so that you can decide which ones are best suited for you, as well as which boots would be the best for certain situations. Let’s get started!
1. Oxford Boots
This style of boot is criminally underrepresented due to its classy relation-the Oxford shoe- taking all of the attention and glory. As the name suggests, the Oxford boot is a high ankle boot version of the Oxford shoe.
This design can make them harder to slip on, but they also offer a more formal and streamlined look
This look has become synonymous with the stereotypical British style, brimming with character and elegance.
It is hard not to imagine an old-timey Victorian chap wearing a pair of Oxford boots as he swings his cane whilst meandering around his estate!
That being said, there is nothing old-fashioned about the Oxford boot. This boot is highly versatile and modern, easily able to fit in with a wide range of outfits from casual to smart casual and just plain smart!
When To Wear Oxford Boots
Oxford boots are perfect for the fall and the winter, as they are most commonly made from leather, which is sure to keep your feet snug and toasty when the temperatures drop.
Due to that aforementioned versatility, there are tons of ways that you can wear these kinds of boots. Blend the classical with the modern by wearing them with some contemporary tailoring.
Contemporary tailoring usually refers to modern cuts that are combined with classical designs, such as a turtleneck sweater that is combined with a traditional two-piece suit.
This blend of traditional and modern styles suits the Oxford boot excellently, creating a nice balance between the origins of the boot and present-day fashion.
2. Derby Boots
You can’t talk about the Oxford boot without mentioning the Derby boot too, as both kinds of boots are often mistaken for one another.
Whilst similar, the two boot styles do have their differences too. The Derby shoe is thought to be more of a smart casual choice that is not as refined or as elegant as the Oxford boot, though both shoe choices are easily able to be used as a smart casual pair of boots.
The visual differences between the two are the most obvious, so let’s take a look at them. The Oxford shoe utilizes that closed lacing design as mentioned above, wherein it can only open in the shape of a “V” when the boot is unlaced.
The sewn-in eyelet facings underneath the vamp at the front of the boot stop that part from opening up entirely.
Derby boots use a tie shoe pattern that is known commonly as a “Gibson”. This pattern allows for the shoe to be opened completely wide at the top via the bottom of the eyelets.
This offers more generosity when it comes to foot entry thanks to the eyelet facing being sewn onto the the top of the vamp rather than being fixed in place.
The Derby originated in the early Victorian period, and was developed with both a hunting and a sporting boot in mind. It became a shoe that could be worn with smart attire, such as country tweeds.
The Derby boot harks back to its roots with its boot form, but with a modern twist that is versatile for all kinds of occasions.
When To Wear Derby Boots
Much like the Oxford boot, the leather of these boots makes them best suited for the colder weather in the fall and winter. They also take after Oxford boots by being perfect for contemporary tailoring.
However, there are a wide range of styles available with the Derby boot that ranges from casual to smart and even a little bit punk rock at times. It all depends on your personal style tastes.
3. Balmoral Boots
Another boot that has many similarities with the Oxford boot, the Balmoral is a walking boot that is named as such as they were designed to be worn by Prince Albert in Victorian England.
The prince was looking for a boot that he would be able to wear on the grassy grouse moors of his estate in Scotland, named Balmoral.
However, he also wanted something that could still be stylish even when inside. Thus, the Balmoral boot was born!
Balmoral is often the term that is used to denote the Oxford shoe, but there are key differences. The main difference is that whilst the Oxford has both shoe and boot variations, Balmorals are only available in boot form.
They are slightly heavier than Oxford boots, but they have various characteristics that are the same too, such as a closed lacing system, round toes, a low heel, leather soles, and a center seam that runs from the heel up to the top of the boot.
Balmoral boots have different variations as well, making them a versatile choice of boot, as you can opt for the style that suits you best.
Some of these styles includes wingtips-wherein the toe is pointed and features extensions that run along both sides of the boots-, full brogues- that not only have wingtips but also have brouging in the middle of the toe cap and along the edges-, and plain Oxford types- which have a lower and upper portion similar to Oxford shoes, but without toe caps.
When To Wear Balmoral Boots
The original Balmoral boots were designed for both practicality and style, and this nature remains the same. They are versatile boots that can be worn in various settings, both casual and formal.
There are all sorts of balmoral boots available, but the thick nature of them wouldn’t make them suitable for particularly hot climates.
The similarity that they hold to Oxford boots makes balmorals a great choice for contemporary tailoring options as well.
4. Chukka Boots
Another highly popular choice when it comes to men’s footwear, Chukka boots are a versatile and stylish choice that can adapt to a variety of settings and situations. They have the ability to complete an outfit perfectly if worn the right way.
Chukka boots are leather boots that are ankle high and feature leather or suede uppers along with rubber or leather soles. They also have open lacing, with two or three eyelets rather than laces that trail down the whole foot.
This is not only a practical feature, but it also gives the chukka its instantly identifiable look. The cut of the boots also does this, thanks to the two whole pieces of either leather or suede that are used to create the boot.
This creates a seam that runs along the middle of the foot, which is a stylish addition to the shoe, but also one that allows you to identify a true chukka with ease. The last identifiable feature of the chukka is the shape of the toe, which is rounded.
Chukkas had their start back in World War II, when a variation on the chukka was worn by British soldiers when they embarked on the Western Desert Campaign.
When To Wear Chukka Boots
As mentioned, the versatile nature of this boot allows for wearing with any sort of outfit due to the simple sophistication. They are well suited for most months, but they don’t offer a huge amount of protection when it gets particularly cold in the winter.
If it is a casual look that you are going for, pair them with a simple t-shirt and well-fitted jeans along with a jacket- such as a Harrington or a bomber jacket- or a comfortable blazer, and you have got a stylish outfit for a relaxing day.
If you are looking for something that is smarter, you can opt for full-grain leather chukkas with a dark color and sleeker toe boxes.
5. Desert Boots
Much like the similarities between the Oxford boot and the Derby boot, desert boots are incredibly similar to Chukka boots. In fact, all variations of Desert boots are a kind of chukka boot, but chukka boots are not all desert boots.
The main difference between the two comes from the functionality that desert boots provide. As their name suggests, desert boots are well suited for outdoor environments- such as on sandy terrain like in a desert- because of their crepe rubber soles.
The first desert boots were introduced in 1949 at the Chicago Shoe Fair by Clarks, and they instantly gained popularity following an article that covered the footwear in Esquire.
The shoes took inspiration from the South African veldskoen shoes- walking shoes made from either soft rawhide uppers or vegetable tanned leather with rubber soles-and became popular for their similar simplistic, lightweight design and robust nature with a strong grip.
When To Wear Desert Boots
The functional yet fashionable nature of desert boots makes them great for a range of casual occasions. You can wear almost anything in terms of casual fashion with a pair of desert boots.
For something to wear with desert boots whilst having a casual day out, consider some jeans with roll up or cuff bottoms (so that you can show off your boots at the same time!).
Pair them with anything you might want, from a sweater to a checked flannel shirt to a button down or just a plain and simple t-shirt.
These are a great choice for smart casual occasions too, particularly colors such as black, beige, or brown. Pair them with a button up and some slim chinos, and you are ready to go.
You can even go for something a little more directly formal by pairing dark desert boots with a laid back style of suit.
6. Chelsea Boots
Possibly one of the most iconic boot choices out there, the Chelsea boot is a unisex boot that has become a staple in the wardrobes of people all over the world.
These are close-fitting boots that are ankle high and feature an ecstatic panel on the side. Another common feature of the Chelsea boot is a tab or loop of fabric that can be found on the back of the boot.
The history of the Chelsea boot is another that stems back to the Victorian era, with the design being credited to Joseph Sparkes Hall, the shoemaker of Queen Victoria.
They were made to be easy to take off and put on again for those who were horseback riding and working.
The name of the boots came from the popularity that they gained in the trendy and affluent area of Chelsea -in London- during the 1950s and 1960s.
Made iconic by infamous British musicians The Rolling Stones and The Beatles, as well as the British model Jean Shrimpton, Chelsea boots quickly became associated with a glamorous and fashionable lifestyle.
When To Wear Chelsea Boots
The subtle sophistication of the Chelsea boot makes them a versatile choice of footwear that can easily be paired with any kind of outfit.
You can easily dress up or dress down with Chelsea boots. Pair them with a t-shirt and jeans to rock a classically casual look, or don a leather jacket with some dark Chelsea boots and skinny jeans to get a rock star vibe.
There are different materials of Chelsea boots too: suede and leather.
Both of these styles of Chelsea boots offer a look that is slightly different but practical, with leather ones being better suited for colder or wetter weather and suede performing well in milder, dryer climates.
Mix and match, and you are sure to find that style that suits you best with Chelsea boots!
7. Jodhpur Boots
Jodhpur boots tend to be seen as an alternative to the traditional standard Chelsea boot, offering the same sleek and smooth silhouette that Chelsea boots have, but with a buckle and strap that goes around the ankle.
The design of the Jodhpur boot makes them an excellent choice for casual, everyday activities, such as their rounded toes and low heels.
These boots also features two parts- the quarters and the vamp- each of which are made from a single leather piece, with the vamp sewn upon the top of the quarters.
That aforementioned strap is also in two parts, each of which are attached to the vamp. They tend to have a buckle that is on the side of the strap too, attached on the inboard side of the boat.
This will extend to about halfway across the ankle, going clockwise around the left boot and counterclockwise on the right boot.
The free end of the strap-on the outboard side- does the opposite by going clockwise on the right and counterclockwise on the left.
A loop on the back of the boot allows the straps to pass through, but this isn’t the only available version of the Jodhpur boot.
There is also a design wherein the straps do not wrap completely around the ankle, with both strap slides being to attached sides of the vamp.
The buckle is on the outboard side, and the buckle length is shorter than the strap on the other side. The free side straps will instead wrap around near the rear of the boot and meet the buckle around the ankle area.
Jodhpur boots have such a practical look and design as they were initially created to be worn for horse riding.
Tall riding boots were not necessary anymore due to the creation of Jodhpur trousers, which would protect the painful rubbing of the inner calf whilst riding.
Long boots were difficult to get on and off, as well as expensive. This is how the convenient ankle length Jodhpur boot came to be.
When To Wear Jodhpur Boots
Due to their history and design, intended to be worn when horse riding, Jodhpur boots make for a great option for casual attire.
Their low heel, close fit and sleek style also allows them to work well with sports coats and suits. They are best suited to a combination of both, so consider opting for a smart casual attire when choosing a Jodhpur boot.
8. Combat Boots
As the name would suggest, combat boots were originally designed for the military and intended to be worn by soldiers for heavy duty activities such as combat training or full on combat scenarios.
These boots had their origins way back in ancient Rome, when legionnaires for the Roman Empire would wear a style of hobnail boots that were known as caligae.
These boots would go on to become a strong staple for the Roman military as well as Roman civilians.
The boots evolved throughout generations and would not only become work boots for modern day workers, but also fashionable footwear for both men and women.
Modern iterations of the combat boot are designed with a combination of grip, foot protection, ankle stability and suitability for particularly rugged environments.
They also tend to be made from hardened- and sometimes waterproof- leather. When it comes to combat boots for fashion, they are a must-have for any wardrobe, particularly when the weather starts to get cold and/or rainy.
These boots tend to be characterized by their rising uppers, their rubber soles, eyelet lacing and hard toe caps. They manage to be stylish and unique boots whilst maintaining that heavy-duty nature, but without becoming too heavy or cumbersome
When To Wear Combat Boots
Combat boots are surprisingly versatile, working well as part of causal attire when paired with skinny, straight leg, flared or even cuffed jeans.
When the weather gets colder, wear them with jeans, a jacket and a beanie to keep your feet warm, cozy and comfortable, all whilst looking fantastic.
9. Engineer Boots
Another style of boot that gets its origins from a working environment, engineer boots were created in the United States and designed as a rugged work boot.
Much like the other boots that we have talked about so far, engineer boots evolved over the decades to become a fashionable style of shoe as well as a practical one.
Engineer boots were developed originally in the 1930s, designed specifically for firemen who would need to work on steam locomotives.
However, the original concept came from around 1860 with the harness boots that were used by the United States Cavalry.
Following the second World War, the boots started to become popular within the motorcycling community and by the 1950s, they became a staple of every teenage greaser’s wardrobe.
When the 1970s came around, punks and skinheads adopted them and decades later in the 2010s, they gained a more widespread popularity in terms of fashion.
These are particularly sturdy boots, usually made from stiff and thick full-grain bull hide leather. The leather will then be oiled, which adds to the flexibility and durability of the boots.
Typically brown or black in color, the boats have double layered shafts that can be anywhere from between 7 and 17 inches in height.
The boots are also gusseted at the very top and can be tightened and adjusted via a steel-buckled strap. They also feature another strap with a steel buckle which is placed near the insteps of each boot.
Because of this heavy-duty nature, they can be quite heavy, though more modern versions can be lighter.
When To Wear Engineer Boots
There is a reason that engineer boots were so popular with greasers, bikers and punk rockers! They make for a great addition to a wardrobe if you have a preference for any of these fashion trends.
However, they can also be worn in the winter in general too thanks to their thick and durable nature.
10. Moc-Toe Boots
Moc-Toes are a hybrid style of boot that combines the sturdy space and comfort of the traditional moccasin with the ankle support, lining and textured or treaded outsole that is usually found in a working boot.
Moc-Toe boots offer an alternative to the standard cap toe or rounded plain work boot, proving to be an asset for workers who need more space within the toe box of the shoe.
They are also available as mid-height or slightly tall boots, usually featuring a paneled appearance and configured stitching in the front of the shoe.
When To Wear Moc-Toe Boots
As well as being a practical pair of boots for certain work environments, Moc-Toe boots are also the perfect footwear accompaniment to a wardrobe that features streetwear aesthetics.
When we say streetwear aesthetic, we are talking about classic streetwear such as cargo pants, flannel shirts and chore coats.
The timeless silhouette offered by Moc-Toe boots also makes them a great addition to a casual outfit or even a work outfit if you have a casual dress code.
As well as that, the paneled, angular nature of the toes of a Moc-Toe boot can offer some much-needed structure if you are wearing a bit of a shapeless outfit!
11. Hiking Boots
Unsurprisingly, hiking boots are boots that have been designed specifically for outdoor activities, such as hiking!
These boots are considered as being one of the most important item that a hiker can bring along with them on a trip, as the durability and quality of the boot are incredibly important.
If they aren’t good quality, then the hiker is at risk of injury and won’t be able to walk long distances.
That isn’t to say that you can’t make hiking boots look super stylish as well as being practical, but the way that they are built makes them a bit stiff due to their focus on providing support for the ankles.
Hiking boots as we know them now got their start in the 1930s thanks to a man named Charles Danner, who wanted to create a sturdy and comfortable walking boot.
The boots could be made at a reduced cost due to being created during the Great Depression, when the market was in a state of severe decline.
With people losing money everywhere, Danner was able to find a place in the market where he could get cheaper materials. He then put them together into a sturdy design, but in a cost-effective manner.
The very first quality hiking boots were created by Danner and then sold for just $4!
When To Wear Hiking Boots
You will obviously want to choose a sturdy and comfortable pair of hiking boots if you are embarking on a hiking trail, but you might also want to get some for a range of outdoor activities, such as general climbing or backpacking.
There are plenty of ways that you can wear them for style, though, particularly if you opt for a fashion brand of hiking boots, such as Timbaland.
On this occasion, pair them with a plaid shirt and some skinny jeans or sweatpants for a comfortable but super stylish look.
12. Cowboy Boots
There is no way that you can mention boots that every guy has to know about without bringing up cowboy boots!
You might be a little wary of wearing them without the running the risk of coming off as cheesy, but there are plenty of ways that you can style cowboy boots without looking like you are wearing a costume.
Cowboy boots- also known as riding boots- have been a part of horse riding and equestrian life for generations. It wasn’t until the industrial age that the boots began to be mass-produced.
Before this, they would be handmade. Because of this, each individual pair of boots would be made with a style that would correspond to the culture of the person making it.
Whilst normally made from leather- cowhide leather specifically- they could also be made with what were considered “exotic” animal skins. These skins could range from the likes of snakes and alligators to eels and stingrays!
These boots tend to come in two different styles: the classical western and the roper. The classical cowboy boots are known for their tall boot shaft, angled heels, and a height of at least mid-calf length.
The ropers are a newer design which features a short boot shaft that would stop just above the ankle, though usually before mid-calf.
The heels are squared off and low, shaped to the boot’s sole, and typically shorter than one inch.
Ropers also feature rounded toes- but more modern styles of roper cowboy boots also feature square toes- and a lace up design that allows for a better fit around the ankles.
When To Wear Cowboy Boots
Cowboy boots can be worn all year round no matter what the season is thanks to their relatively lightweight but durable nature. They are usually worn casually, with jeans, flannel or collared shirts and belts.
Cowboy boots have a sense of fun to them, but they are also highly practical due to their initial design, intended to be used with horseback riding and other physical outdoor activities.
13. Bean Boots/Duck Boots
Bean boots- otherwise known as Duck boots- are perfect for the wet weather, but are also highly fashionable, being considered as part of New England prep fashion.
Created in 1911, Bean boots were invented by Leon Leonwood Bean, who was an avid hunter and outdoorsman from Freeport in Maine, New England.
He wanted to create a pair of boots that would keep his feet dry whilst outdoors in the rain.
In doing so, he combined rubber taken from the sole of rain boots with leather uppers and asked a local cobbler to create the shoes. Thus, duck/bean boots came to be!
Much like the original iterations, these boots are still made with rubber soles and a rubber top and are designed to combat harsher weather conditions.
They come in various different styles nowadays, thanks to them becoming highly popular on the fashion scene, as well as a practical pair of rain boots.
They also tend to have a fabric sleeve atop of the leather top, added for additional warmth and protection.
When To Wear Bean/Duck Boots
These are definitely boots that are best suited to the wet and cold weather, but that doesn’t mean that you can’t create your own rainy day fashion with a pair of these boots.
Simply pair them with a pair of skinny jeans and a raincoat and voilà! You have a fashionable yet practical wet weather outfit.
14. Mukluk Boots
Whilst we are on the topic of weather specific boots, Mukluk boots are boots that have a rich history amongst the North American Lakotan and Inuit tribes- as well as other tribes in that area- that are still popular today in some of the coldest areas.
Mukluks are boots lined with fur that are traditionally made with the skin of seals or caribous, and they are still a staple in the wardrobe of North American tribes.
They feature a soft leather insole that maintains sturdiness whilst remaining comfortable. The term comes from the Yupik language- spoken by the indigenous Arctic tribes- meaning “bearded seal”.
Designed for warmth in freezing conditions as well as for hunting, mukluks are an incredibly functional boot that helps keep moisture away from the ankles and feet to avoid frostbite.
Despite being created purely for function, mukluks have evolved to become a fashionable form of footwear whilst still maintaining the elements that make them so practical in harsh weather environments.
When To Wear Mukluks
If you know you are going to be travelling somewhere that gets very, very cold, consider getting yourself a pair of mukluks to keep your feet warm and dry whilst not over burdening you with any unnecessary heaviness.
They can also be a stylish piece of fashion thanks to modern designs, which can include intricate beading and patterns.
15. Service Boots
Service boots are another kind of boot with designs that were inspired by classical military issue boots, built with the same combination of rough out and smooth leathers.
These leathers are usually oiled to create durability and flexibility, as well as a specific look and texture.
Service boots tend to have block heels with rubber soles, made to withstand the test of time whilst maintaining comfort in all manner of situations.
These kinds of boots were originally designed to be used for vigorous and heavy outside work, so they have a sturdiness and supportive nature to them.
The modern take on these boots will also incorporate stylish additions as well, making them incredibly versatile.
When To Wear Service Boots
Much like the other sturdier boots on this list, these are better suited for colder weather. That being said, they are a great option for manual work all year round.
16. Work Boots
The final boot that we are putting on this list has to be a classical pair of work boots! A decent pair of these boots can last for a lifetime and can have multiple uses.
Whilst they are not exactly boots that you are going to wear to a smart event, you can definitely utilize them for any heavy-duty activities that you might need to take part in, both at work and at home.
Work boots tend to come with either a composite toe or a steel toe, keeping your toes and feet nicely protected from anything large and heavy.
This is particularly useful in working environments that involve heavy machinery or metals.
Steel toes are definitely stronger, but you will only really need them if you are working in a role that specifically requires it. Composite toe work boots are lighter but still able to take some heavy impacts.
When To Wear Work Boots
Funnily enough, the best place to wear work boots is at work!
You could also wear them for outdoor activities, but keep in mind that for anything that requires a lot of walking or general maneuverability- like hiking- might not be appropriate, as work boots can be heavy.
They are great for the likes of fishing and camping, though.
Final Thoughts
So, there you have sixteen pairs of boots that any and all guys simply have to know about and add to their wardrobes!
Whether you are looking for a pair of boots for hot weather, cold weather, outdoor activities, work or for a smartly dressed occasion, you are sure to find one of these boot options suitable.
Hi, my name is Joseph Pais and I have been living in London for twelve years. I first moved out here straight after university for an internship in a top accounting firm. I had never been someone to dress up, so I started my time here wearing sweats, hoodies, and the occasional pair of jeans.
If you’re struggling with fitting in within London, let me give you a piece of advice - change how you dress yourself. Sweats are for at home when no one can see you, and impressions influence everything.
I want to use my website to show you how to present yourself in cities to ensure that you’re not being held back by your clothing choices. So, let’s get to work and get you that bit closer to success!
