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Your Ultimate Guide To Men's Boots

Your Ultimate Guide To Men's Boots

19 Apr 2024

Your Ultimate Guide To Men's Boots

By James Shackell

There are dozens of different types of boots, and we could write huge, leather-bound books on men’s boot styles. But for the average guy in the street looking for a kebab, you can pretty much break men’s boots down into four types: Chelsea boots, chukkas, military boots and Cuban heeled boots. These are the boots you’re going to see most often. They’ll take you everywhere from the boardroom to the cocktail bar. You don’t necessarily need all of these in your wardrobe, but it’s good to know which boot is which.

Pull up a chair and get comfortable. This is our ultimate guide to men’s boots.

Things to consider when buying men's boots

When you’re on the market for a new pair of men’s boots, there are a few things that you should keep in mind. When shopping for men’s boots, it’s important to consider the purpose, fit and materials of the boots in question. The sheer variety of boot styles available can be overwhelming, but by asking yourself these three questions, you’ll be well on your way to finding the perfect pair of boots for your lifestyle and needs.

What kind of pants are you wearing?

When it comes to mens boot fashion, there are a lot of factors to consider. Boots with suit pants require a specific type of boot to create the right look. Slim-fit pants, call for a slimmer-toed boot. For the AQUILA range, that’d be something like the DRAPER or the OSBOURNE 2.0 (notice that long, slim profile and chiseled point). With looser fitting pants, jeans or chinos, you can get away with a more rounded-toe, like the DEXTER. As a general rule, the more rounded the toe, the more casual the boot.

When will you be wearing your boots?

The type of boots you choose also depends on when and where you’ll be wearing them. Will you be wearing them to the office? On that weekend road trip? To your mother-in-law’s for dinner? Let the occasion dictate the style. For a semi-formal option that can transition from work to a footy match, something like the NORTON is probably best. If all you need is a solid casual option, look for a suede chukka boot, like the BOBBY.

Will your boots get wet?

Obviously you can’t predict the weather (even weather reporters struggle with that), but if you reckon there’s a chance of getting your boots wet, stick to leather, not suede. Suede boots can dry out and get water marks if exposed to moisture. Think about your sole too: for rainy days you want a thick, rubber sole to protect your boot’s upper as much as possible.

Chelsea Boots

Chelsea boots are the most versatile, reliable, timeless boots you can own. You’ve probably seen about a million of them as they are a very popular boot in men's fashion. They’re close-fitting, ankle-high boots with an elastic side panel, invented in the 1800s for Victorian royalty (and later made popular by The Beatles and The Rolling Stones). Chelsea Boots are sometimes made from a single piece of leather, but usually the upper is two pieces stitched together: the front (AKA ‘vamp”) and the back (AKA ‘quarters’).

Good for…

That’s the beauty of the Chelsea boot – they’re good for everything. Depending on the shape, fabric and toe, you can wear these with three-piece suits or ripped, punk-rocker jeans (although we’d personally recommend some good quality, intact denim). Polished Chelsea boots are a great office switch from brogues or oxfords. Just make sure they’re tapered, with a thin, chiseled toe.Here's a fashion tip for men's black boots - wear them with a grey suit, or dark brown boots for navy. If you want a more casual Chelsea boot, look for textured leather or (even better) suede. Suede Chelsea boots are the perfect weekend footwear.

Key Chelsea Boot Styles

We’ve got a big range of Chelsea boots for every occasion and outfit, but if we had to pick one, it’d be the OSBOURNE 2.0. This is the Cadillac of Chelsea boots: hand-made in Italy, lined with pig leather and finished with tough, Blake-stitching. Every pair is dip-died too, which gives them a unique patina. We’ve been making boots for over 60 years, and everything we’ve learned has been lovingly poured into the OSBOURNE.

Desert Boots

Desert boots are also known as Chukka boots. Well, sort of. All desert boots are Chukkas, but not all Chukkas are desert boots (make sense?). Imagine the style and sophistication of an ankle-height boot, with the pillowy comfort of a sneaker. They’re the most comfortable boots, and the most casual option when it comes to men’s leather boots. Chukkas are defined by two or three eyelets, thin laces and that low-rise, ankle-length cut (desert boots, in case you’re interested, technically have a light crepe sole). They were originally worn by British soldiers in Africa during WWII.

Desert Boots are Good for…

Chukkas and desert boots are strictly for casual outfits, even the leather ones. Don’t try to wear these boots with a suit – it’ll just look weird. Having said that, there’s no reason chukka boots can’t look smart and classy. Matched with some slim-fit, dark denim jeans, or good-quality tapered chinos, desert boots are an acceptable ‘smart casual’ option. Use these for weekend footy matches, long, country road-trips and backyard barbecues.

Key Fashion Styles

This depends on whether you’d like to go leather or suede. For that textured, casual look, the soft-suede SCOUT is probably your best bet. Match these boots with simple jeans or khaki chinos. If you’re after something dressier, a leather Chukka might be more appropriate. Our personal favourite is the MANNING.

Gleeson Black Suede Chukka Boots

Military Boots

Originally, military boots (aka ‘combat boots’) did exactly what they said on the label: they were boots for the military. But men's boot fashion doesn’t discriminate when it comes to inspiration, and after a quick detour through punk, grunge and heavy metal, military boots have emerged as a mainstream, pop-culture staple. A lot of people wear these boots for comfort and durability. They’re often waterproof, with a soft, shock-absorbent inner sole, and a high, calf-length upper.

Military Boots are Good for…

Military boots are surprisingly flexible. You can match them with workwear (maybe utility pants and a plain white t-shirt), casual wear (some tapered dark jeans and a bomber jacket) or even smart-casual (throw on some dark pants, a dark knit jumper and a sharp, woolen overcoat). The trick is getting the trousers right: you can’t let them dangle too low or they’ll obscure the leg of the boot. Either hem your pants or (better yet) cuff them high on your calf. You want to show off that chunky, leather upper.

Key Military Boot Styles

Like any other men’s boot style, you need to think about shape and fabric for a good quality boot. For that smart, after-dark look, stick with polished leather: The Ingram Military Boot is usually a good choice. Just remember to use a shoe tree when you get home, and give them a polish every month or two. Look after your military boots and they’ll look after you.

Cuban Heeled Boots

As far as heels go, Cubans are relatively small, but most guys aren’t used to the extra height, so they can take some getting used to. Think of them as ‘cowboy heels’ or ‘rockstar heels’: that iconic, chunky, low-rise, tapered wedge. They were original designed for 9th century Persian soldiers, but hit the mainstream fashion in the 1960s with the British ‘mod’ movement. Lots of style icons have rocked Cubans over the years, from Jagger and Bowie to The Horrors and Noel Fielding.

Cuban Heeled Boots are Good for…

The trick with Cuban heels is confidence. You need to believe in the heel. With confidence and a good Cuban heeled boot you can go almost anywhere. Channel some 60s swagger with a slim, charcoal suit and Cuban-heeled Chelsea boots. Or go for more of an indie vibe with skinny jeans, a loose t-shirt and a solid belt buckle for this type of boot. Whichever look you choose, you want slim, tapered pants or jeans. Nothing loose and baggy. Cuban-heels are all about that long, sharp silhouette: you don’t want to mess that up with straight-fit chinos.

Boot maintenance

Keeping your boots looking great is a must, regardless of the style of the boot you're wearing. We’ve already written a comprehensive guide to shoe care, but there are a few simple rules every guy needs to know about boot care – no matter what style of boot you’re wearing. Here are some important tips for keeping your boots in top shape.

Shoe trees

Shoe trees are wooden, foot-shaped things that sit inside your boots when you’re not wearing them. They help protect the shape and fit of your boot. You don’t have to get shoe trees, of course, but we highly recommend them. Especially for Chelsea or military boots (anything above ankle-height, really). A good shoe tree is a small investment that will go a long way in protecting your boots.

Stain protection

Before you take your new boots for a test drive, invest in a good-quality stain protector. It’ll help seal the fabric and repel water. This is especially important for suede boots, which tend to stain and damage easily. We recommend the Aquila Eco Water & Stain Protector.


You should clean your shoes regularly, but you don’t necessarily need to polish them every night by the fire. Over-polishing boots is probably the most common mistake: excess polish creates this layer of build-up, which affects the leather over time. Just use a little bit, and repeat the process every few months.