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20 Best Boots For Men [2016 Edition]

Nothing says ‘get it done’ like a good, solid boot. As the lines continue to blur between the functional and the fashion-y, stylish men this season need to pick up a pair of killer boots from the crème de la crème of luxury.

No longer reserved for outdoor adventurers, farmers or jackaroos the boot’s sporty antics and hard yakka history have softened a lot, letting it walk on in as a wardrobe staple for men. So, let’s take a look at the ins-and-outs of the classic footwear.

Breaking It Down


There is no such thing as a standard boot. A part from the generic types – be it, the Chelsea or the Chukka, there exists today a plethora of hybrid models – the hiker boot with a Derby sole or the biker with a cowboy decorative inlay.

Then, there are the varying finishes, textures and details across each model, as well as a difference in colour and fabric. Exhausted? Don’t be. Read on to unlock the key styles for this year (and how to work them), before clicking through the slideshow for the 20 best boots for men in 2015.

Boot Types

Chukka Boot


The chukka is named after a period of play in polo – the ‘chukker’. Hailing from the aristocratic sport, the chukka boot – in contemporary times – rides seamlessly as a smooth choice with smart casual attire and suits, depending on the sole.

Traditionally made in suede or calfskin, the chukka remains that way today and is appreciated for its short shaft, which also makes the boot an easy choice to be worn with tailored shorts.

How To Wear It

The chukka wears well with this season’s double denim trend, opting for raw denim jeans, a chambray shirt and a black denim jacket for an American workwear look. Otherwise, white chinos and a polo shirt give back something more quintessentially preppy. This boot is a wardrobe staple for 2015.

Chelsea Boot


We have the Beatles and London’s Fifties rock/pop culture for the Chelsea’s resurgence into men’s fashion all those years ago. Named after the borough located in the south west of the English capital, the Chelsea boot’s sleek, laceless designer makes a functional beauty to the stylish time-poor.

The Chelsea is recognisable for its elastic side panels for ease of slipping on and taking off, and in contrast colours agains the leather, the panels make for an instant style statement..

The boot also comes in different heel heights – from chunky and durable, to slim and formal, meaning the Chelsea works just as well with selvedge jeans and workshop coat, as they do with tailoring.

How To Wear It

The Chelsea takes it lack of laces, and absence of eyelets and metallic hardware, in its stride. Made in polished leather, pair the Chelsea with a super wool suit, shirt and tie – perfectly office or wedding ready. The rider-inspired Chelsea looks best in suede and look to brown for a change away from black.

Biker Boot


The vintage Hollywood trend continues to rev-up the blood. Drawing inspiration from the original bad boys – Brando and McQueen, the biker aesthetic rides ever so well in to 2015. I’m not talking about gang member tats and handlebar mo’s; more the chic leather and sleek black – all part of being a modern biker sans bike.

Always in leather, and in black or dark brown, the biker boat is distinguished by a side, asymmetrical zip or a leather strap with metal buckle detail – the latter being a slip variety, rather than zipped.

How To Wear It

Unlike other types, the motorcycle boot looks best kept to the tune of the biker. That means, black jeans and perfecto jacket, or washed grey denim with biker leg details paired with a plain tee. Don’t roll the cuff on pants with the biker, as you would a Chukka or hiking boot, it sabotages the care-free attitude needed to pull this look off.

Hiker boot


The hiker boot has been modernised this season – for a look that is a little more adventurous but without the harsh practicalities needed to climb a mountain. Made from leather with the occasional synthetic panels for a sports edge, the eyelets and laces of this boot are super sturdy and extremely practical.

The hiker boot is crafted with a mid-rise shaft and leather outer sole with a grippy heal for traction. Other hiker boot styles a have a flat sole, made from crepe, leather or rubber, and often come in a contrast sole colour such as white or black. This type of boot also features coloured laces. It’s the most casual of all the boots, and should be kept far, far way from a suit.

How To Wear It

Paired with chinos or slim fit denim, the hiker boot works well under wax-coated jacket or duffel coat, making hard work of a smart casual look. Looser jogger pants and a satiny, bomber jacket accentuate the active vibe of the shoe, treating it more like a sneaker than a boot.

Dress Boot


The dress boot is the most formal variety. And, like its shoe counterpart, it comes in two styles: the Derby or Oxford. The Derby has eyelets that stitched on top of the shoe vamp, creating an open front, appearing more casual (almost militant looking) compared to the Oxford variety.

How To Wear it

And the dress boot is the most versatile of the group; pairing luxuriously with a suit for work, cotton trousers, shirt and blazer a down played tailoring fit, or denim and a tee for an off-duty model vibe.


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7 Jul, 2015

Benjamin Fitzgerald

Style Contributor