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Your Ultimate Guide To Men's Boots

Your Ultimate Guide To Men's Boots

27 May 2022

Your Ultimate Guide To Men's Boots

By James Shackell

There are dozens of different types of boot, 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 broad categories: Chelsea boots, Chukkas, military boots and Cuban heels. 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 looking at men’s boot styles, there’s a few things to keep in mind. Use these three questions to steer yourself in the right direction.

What kind of pants are you wearing?

Think of your pants and your boots as a team. They have to work together. Suit pants, or slim-fit pants, require a slimmer-toed boot. For the AQUILA range, that’d be something like the WARNOCK or the EASTWOOD (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 DAYTON. As a general rule, the more rounded the toe, the more casual the boot.

When will you be wearing your boots?

Finding the right type of boot for each occasion is half the battle. Think about when and where you’re going to wear your boots. To the office? On that weekend road trip? To your mother-in-law’s for dinner? Let the occasion dictate the style. So if you wanted a semi-formal boot that could go from work to the footy, something like the BEAUMONT is probably best. If all you need is a solid casual option, look for a suede Chukka boot, like the DORADO.

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. 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. And remember: black boots with a grey suit, dark brown 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 Styles

We’ve got a big range of Chelsea boots for every occasion, 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 about 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.

Good for…

Chukkas and desert boots are strictly for casual wear, even the leather ones. Don’t try to wear these 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, 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 Styles

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

Military Boots

Originally, military boots (aka ‘combat boots’) did exactly what they said on the label: they were boots for the military. But 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 them for simple durability and comfort. They’re often waterproof, with a soft, shock-absorbent inner sole, and a high, calf-length upper.

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 Styles

Like any other men’s boot style, you need to think about shape and fabric. For that smart, after-dark look, stick with polished leather: 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 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.

Good for…

The trick with Cuban heels is confidence. You need to believe in the heel. With confidence and a good Cuban heel 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. 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.

Key styles

The EASTWOOD is a good, gentle introduction to the Cuban heel. It comes in blue, black, tobacco or stone suede, and it’s got an elastic side panel and heel tab. Think of the EASTWOOD as your ‘rockstar’ boot: all you need is some dark, skinny jeans, an open-collar black shirt and a charcoal overcoat.

Boot Maintenance

We’ve already written a comprehensive guide over here, but there are a few simple rules every guy needs to know about boot care – no matter what style of boot you’re wearing.

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).  

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.