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The 7 Boot Styles All Men Should Own

A guide to the key types of boots for men, including what they look like, how to wear them and the best brands for each.

Words by: Paddy Maddison

Getting cold feet about your fall/winter footwear rotation? In our experience, the best way to solve that is by giving subpar footwear the boot. Sneakers, loafers and dress shoes are all well and good when the sun’s shining, but when the going gets tough, you need something that’s up to the challenge.

Step number one: acquaint yourself with the key boot styles for men. Knowing your Chelseas from your chukkas will make the job of finding the right stompers a lot easier. This way you’ll be clued up on the ins and outs of the various different breeds of boot, and you’ll be better informed to pick the ones that best suit your personal style and day-to-day life.

To help you reach that point, we’ve compiled a sort of unofficial spotter’s guide to the key types of boots for men, including what they look like, how to wear them and the best brands for each. Here’s everything you need to know.

Derby boots

Man wearing black grained leather Derby boots with tailored black pants


You might already be familiar with the Derby shoe. For the uninitiated, it’s a style of dress shoe that features an ‘open’ lacing system. This is where the eyelets are stitched on top of the vamp, resulting in a more casual look than that of its closed-lace counterpart, the Oxford shoe.

The Derby boot, as you might already have deduced, is the Derby shoe’s slightly taller sibling. It’s usually around ankle height with a flat leather or rubber sole and thin round laces. More casual versions feature details like broguing to the uppers or decorative stitching.

How to style Derby boots

The Derby boot leans more towards the dressy end of the smart casual spectrum. This means it’s a boot that can be worn with a suit, but  is equally at home slumming it with jeans and casual shirts at the weekend.

Derby boots with details such as broguing are generally regarded as more casual than those without. These are the best types to go for if you’re looking for something purely for off-duty, day-to-day wear. They go great with everyday staples like raw selvedge denim jeans, flannel shirts, T-shirts and outerwear.

A plain Derby boot is a better option if you intend to wear it with smarter pieces like a blazer and tailored trousers. A smooth leather Derby boot in black will work nicely with a suit, or opt for a toe-cap version if you want something that can turn its hand (read: foot) to a little bit of everything.

The best Derby boot brands

This is a traditional boot style, so if you’re looking for the best of the best, it’s a good idea to take your money to a traditional bootmaker. Northamptonshire, England, is known for its boot and shoemaking history and is home to renowned names like Grenson, Crockett & Jones and Cheaney.

For a more affordable alternative, check out what direct-to-consumer footwear brands like Morjas, Velasca and Cobbler Union have to offer. These brands all offer excellent quality materials and handmade construction but without retailer markups.

Chelsea boots

Man wearing tan suede Chelsea boots with blue jeans


This slip-on boot is named for its proliferation around London’s trendy King’s Road in the 1960s. It was a big part of the mod subculture and a common sight on the feet of rock stars and celebrity tastemakers.

The classic Chelsea boot features a flat sole with a slight heel, a smooth leather or suede upper with elastic gussets to the sides and an ankle-height silhouette. That said, there are contemporary versions that stray from this template. Chunky versions with lugged ‘commando’ soles are becoming more and more popular, and there are some more technical variations made from weatherised materials too.

How to style Chelsea boots

Much like the Derby boot, the Chelsea boot can slot seamlessly into almost any outfit. This is because it’s simple, low profile and timeless, which makes it incredibly versatile and easy to dress up or down.

Worn with tailoring, a black or brown Chelsea boot can instantly switch up the feel of your getup. A simple slim-fit, single-breasted suit is a great example. Worn with a regular pair of dress shoes, it’s a pretty pedestrian look, but switch them out for a pair of Chelseas and straight away the whole thing has much more energy and attitude.

Alternatively, style them with smart casual staples like Oxford shirts, jeans and chinos.

The best Chelsea boot brands

Again, check out what the Northamptonshire boot brands mentioned above have to offer. Outside of that, there are a number of companies specialising in Chelseas. The one that immediately springs to mind is R.M. Williams. It’s a historic Australian brand that started life crafting slip-on boots for ranchers and bushmen, but has since infiltrated the luxury shoe market.

Alternatively, take a look at Dr. Martens for something a bit more casual with bags of attitude.

Moc toe work boots

Men's black leather moc toe work boots worn with light denim jeans


This blue-collar boot was born in the workshops, garages and job sites of North America. It’s a sturdy boot, usually made from thick leather with a stitched toe and either a wedge or commando sole.

Work boots are designed to take a beating on a daily basis. As such, the best ones are built to last, often with heavy duty materials and traditional construction techniques like Goodyear welting, which makes them easier to resole.

How to style moc toe work boots

This is not the sort of boot that naturally mingles with tailoring in fancy establishments. It’s built for the daily grind and should be styled as such. We’re talking heavy denim, thick flannel shirts, chore coats, gilets and heavyweight T-shirts.

The moc toe work boot’s robust build makes it an excellent daily driver. It’ll happily stand up to the rigours of everyday life, and when it does give up the ghost, it’s easy enough to repair. For maximum versatility across your day-to-day wardrobe, we’d suggest going for a simple brown leather option. This will work well with pretty much everything, in all seasons.

The best moc toe work boot brands

The best brands for moc toe work boots are the ones with a history of designing and making tough-as-nails footwear for demanding jobs. Perhaps the best known is Red Wing, which has been making some of the most recognisable moc toe boots around for well over a century.

Also worth checking out are Danner and Thorogood – two Made in the USA brands that specialise in hard-wearing footwear for the workplace.

Round toe work boots

Men's brown leather round toe work boots worn with navy pants


This plain toe alternative to the moc toe work boot is essentially a beefed up Derby boot in terms of its shape and styling. It’s still built to stand up to the grind, but does away with the stitching around the toe box in favour of a smooth, one-piece front section.

Aside from this, the round toe work boot is essentially the same beast. It’s usually cut just above ankle height, made from thick leather, nubuck or suede, and features a lugged commando sole for traction on rough or slippery ground.

How to style round toe work boots

This style of boot belongs firmly to the workwear family. This means it works best with casual pieces, particularly those that have their roots in blue-collar applications. Again, this means things like jeans, heavyweight overshirts, carpenter pants and worker jackets.

Because of its laid-back looks, it’ll pair well with most casual garments, but it’s not the sort of thing you should be wearing with tailoring or even smart casual fits.

The best round toe work boot brands

Many of the best brands for round toe work boots are the same ones that make great moc toe work boots. Red Wing, Thorogood and Danner are all still excellent options.

But perhaps the best-known round toe work boot is Timberland’s iconic 6″ model. It’s an all-time classic that’s beloved by everyone from weather-beaten workers to East Coast hip-hop heroes – and it’s a surprisingly affordable boot, too.

Chukka boots

Man wearing dark brown suede chukka/desert boots with brown woll pants


The chukka boot is a style of casual ankle boot popularised by Clarks with the world-famous Desert Boot. It’s usually made from soft suede or leather, has two or three eyelets and traditionally has leather or rubber soles. The Clarks Desert Boot features a distinctive crepe rubber sole.

Chukka boots were originally worn by British soldiers in the Western Desert campaign during the Second World War. It was shortly after this, in 1950, that Clarks made the style into a casual boot for civilian use, and it wasn’t long before it became a must-have fashion item.

How to style chukka boots

The chukka boot is a casual style through and through. It pairs well with everyday essentials like jeans and T-shirts, but it can also be dressed up with smart casual pieces and even soft tailoring.

This makes it extremely versatile and perfect for those who like to keep their footwear rotation stripped back and simple.

The best chukka boot brands

Clarks invented and popularised the style we all know and love today, so your journey for a new pair of desert boot should always start there. Affordable, comfortable and available in a wealth of materials and colourways, chukkas don’t get much better than this.

If you’re looking for an upgrade on the original, there are a number of brands offering elevated takes on this everyman silhouette. Traditional shoemakers such as John Lobb, Edward Green and Tricker’s handcraft their desert boots using the highest grade hides, creating desert boots that look and feel high end.

Want something a little different? Try the likes of Visvim, which adds fringing to the upper, or Kleman, which specialises in chunky workwear-inspired versions complete with thick lugged soles.

Hiking boots

A pair of black leather classic hiking boots worn with off white jeans


Back before the use of synthetic materials and lightweight EVA midsoles was commonplace, hiking boots were heavy leather things with D-ring eyelets and hand-stitched uppers. Today, these traditional hikers have been usurped by lighter, more breathable modern alternatives for alpine activities, but in terms of aesthetics they remain unchallenged.

A classic hiking boot has a plain round toe, a gusseted tongue, metal D-ring eyelets, a thick commando sole and a lacing system that extends down onto the top of the toe.

The upper is generally made from thick leather or suede, although the latter is less practical for winter use, which is when this particular style of boot really shines.

How to style hiking boots

Classic hiking boots look great, but they’re not the most versatile of footwear. The key to pulling them off lies in balancing out the proportions. This is a bulky boot, so it doesn’t pair terribly well with anything slim fitting. Instead, stick to regular-cut pants, relaxed-fit tops and oversized outerwear to keep the balance.

Casual, workwear-inspired fits are where the classic hiking boot looks its best. It’ll sit nicely below a pair of heavyweight raw denim jeans or some relaxed fit cargo pants, and it’s particularly at home during the winter months.

The best hiking boot brands

Danner is the original and best when it comes to this style of boot. The Oregonian brand’s Mountain Light boot is perhaps the best example of this type of footwear and has remained mostly unchanged in the 50 plus years it’s been around.

Elsewhere, Italian brands Fracap, Diemme and Velasca are well known for this style of boot too. For a more fashion-led option, check out the likes of Moncler, ROA and Brunello Cucinelli.

Technical hiking boots

Men's technical hiking boots worn with black pants


Technical hiking boots are the modern alternatives to classic hiking boots. They forgo the all-leather construction in favour of lightweight synthetic materials, mesh and Gore-Tex membranes. They’re generally much lighter, more comfortable to wear right out of the box and often feature bolder, brighter colours.

These are the boots generally favoured by modern alpine athletes, but they’ve made inroads into the style world too. Thanks to fashion’s ongoing fixation with functional pieces, many high-end brands have put their own aesthetically led spin on this style of boot, including the odd one like ROA that’s managed to build an entire label around it.

How to style technical hiking boots

If you’re a subscriber to classic style, you might find a technical hiker more daunting than its classic counterpart. But don’t worry, the basic idea is much the same. It’s all about balancing out the bulky shape and any bright colours with the rest of your outfit.

Steer clear of skinny or overly slim silhouettes, and instead opt for regular-fitting pants, loose tees and relatively boxy outerwear.

If your boots feature hits of bright or bold colour, keep the rest of the outfit simple and restrained. This means the boots won’t be fighting with anything else for attention.

The best technical hiking boot brands

There are two routes you can take here. One is to go for an established outdoor brand that specialises in technical hiking boots, and the other is to go to a fashion brand that makes the style.

In the former camp, La Sportiva, Hoka One One and Salomon are all excellent options. For a more fashion-forward take, check out ROA, Diemme and Y/Project.