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The Essential Guide to Men's Boots

The Essential Guide to Men's Boots

A timeless footwear option, boots are a must-have for every gentleman when the Autumn and Winter months arrive. However, you don’t want to leave it until your toes are frostbitten, or you are ankle-deep in snow before you realise its time to invest in a quality pair of boots. At Cheaney, we have a wide range of luxury men’s boots on offer in a wide range of styles. But knowing which pair is the best option for you, your style, or occasion can be a minefield in itself. This is why we are proud to introduce the essential guide to men’s boots from Cheaney. 

Here, you will find a rundown of all the classic boot styles we have on offer now, and we will break them down into how they can be worn, where you should wear them, and how to take care of your premium pair. Plus, many more details we feel you should know about your new investment.


To kick things off, let's start with the perfect ‘beginners boots’. If you’re a shoe lover and haven’t ventured into the world of boots before, then we think that
CHUKKA BOOTS are the perfect option for you. This simple silhouette is characterised by its ankle-length, thin laces, and two to three eyelets.


Chukka boots are the perfect option for smart-casual style and can be dressed up or down depending on your requirements. Whether it's a weekend stroll with friends and family, or for a dressed down day in the office, chukka boots are the ideal choice. Plus, if you’re not confident in wearing boots yet and prefer the easy styling of shoes, chukka boot’s short height makes them easy to wear. 


Pair chukka boots with smart jeans and a jumper for a casual, weekend look. Their simple design makes them perfect for throwing on and still looking effortlessly smart. For a more thought-out look, don a pair of blue jeans with a casual, white shirt, and finish the ensemble with a denim jacket.

If you’re looking for something more refined, choose a pair of black chukka boots for a more sophisticated option that achieves an elegant appearance. Style black chukkas with dark jeans or chinos, a crew neck t-shirt and a blazer for a perfect party outfit.


Although chukka boots are a more versatile option that can be worn all year long, they still require care against the elements. We recommend investing in a high-quality suede protectant spray and keeping them in good condition with a CHEANEY SHOE BRUSH.


For a more masculine silhouette, choose a pair of
MEN'S MILITARY BOOTS. More durable and long-lasting than other styles, military boots are ideal to have in your collection. Wear them in the Winter months for full coverage for your feet and ankles without any worry of them falling apart. 


Of course originally designed for men and women in the military, this popular style has now found a secure place in the world of fashion. Crafted for their comfort and durability, military boots are famed for their rising uppers and a multitude of eyelets that give it a distinctly vintage appearance.


With their bold appearance, it is not hard to see why military boots are perfectly paired with anything masculine or military-inspired. They’re best worn for a laid-back, casual look, and so we recommend pairing them with dark jeans and plain t-shirts. Finish the look with a leather or bomber style jacket slung over the top for a relaxed but effortlessly cool ensemble. For Autumn, you could style military boots with a flannel shirt for an on-trend and season-appropriate style.


Luckily, military boots are low-maintenance compared to other styles. However, that doesn’t mean you shouldn’t still do your best to take care of them. If they are looking dirty, wipe clean with a cloth and take the time to POLISH them with a proper kit from our collection. 

For a similar style, you can explore our range of HIKER BOOTS also available online. 


Right bang in the middle of the casual to smart spectrum lands the classic brogue boots. Originated in Scotland and Ireland, the modern BROGUE BOOTS were crafted for functionality in water. Its iconic perforated style allowed for water to drain through the shoes when walking in wet terrain. Of course, today, we recommend that you keep your brogue boots out of direct contact with rain in order to keep them in perfect condition, as this unique detail has evolved to be solely for decoration only!


The iconic design of the brogue boot makes them a popular choice for any well-dressed gentleman. Characterised by its many perforations and unique detailing, brogue boots are an easy way to add excitement and style to any outfit.  Ideal for smart-casual occasions, brogue boots can easily be dressed up or down for the office, social events, and special occasions. They’re also a great option to wear the majority of the year in Autumn, Winter, and Spring.


With their sophisticated design, you should certainly steer clear of anything too casual when wearing brogue boots. Put away the hoodies, graphic t-shirts, and anything too brightly coloured. Instead, pair your brogue boots slim, dark denim and a light jumper for a relaxed look. They can also be dressed up just as easily with formal trousers and a jacket, so if you’re looking for the perfect versatile pair, we highly recommend brogue boots.


As brogue boots are designed to smarten up an outfit, we recommend that you keep them polished at all times. We have a wide range of excellent POLISH SETS and BRUSHES designed especially for use with our range of high-quality leather boots for you to explore.


For a smart and sophisticated option, the most refined silhouette is the iconic CHELSEA BOOT. A wardrobe staple, men’s Chelsea boots have a timeless shape and design that will never fall out of fashion. Dating back to the Victorian era, Chelsea boots are famed for their easy to slip on construction, rear tab to the uppers and slight heel. However, their current name is theorised to have come from the boots major popularity in the Chelsea region of London in the 50’s and 60’s. During this time, Chelsea boots were worn heavily by the likes of mods, as well as The Beatles and even The Rolling Stones. 


For a smart ensemble, we recommend choosing a pair of traditional leather Chelsea boots. With a sleek and smooth aesthetic, leather Chelsea boots can be worn in place of a dress shoe with more polished outfits. For formal events, they can be worn with a full suit without looking out of place. If your event is only semi-formal, or you’re not sure on the dress-code, then opt for suede Chelsea boots instead. This style infuses a relaxed aesthetic into your ensemble, to keep it refined and urban choose black suede or explore brown suede Chelse boots for a relaxed, Country look.


Chelsea boots have a very versatile style, which means they can be dressed up or down for all manners of occasions. With their simple design, Chelsea boots complement a range of styles, outfits, and colours without looking mismatched, so we think they are a perfect addition to any gentleman's wardrobe as a staple pair of boots. Swap out trainers for Chelsea boots for weekend get-togethers or dress-down days in the office, or pair the boots with chinos and a blazer for the perfect business casual look. Our top tip to make sure you always look great in your Chelsea boots; make sure the leg of your chosen trouser or jean always sits just above the top of the boots.


As Chelse boots have such a smart reputation, we recommend you keep them in pristine condition. You can do this by polishing them regularly with a high-quality POLISH SET from our collection. If you have opted for suede Chelsea boots, then make sure you use a SUEDE BRUSH to remove any dirt if they start to show signs of wear.

Choosing the Right Boot

Now that you have read through our essential guide to boots, it's time to pick the perfect pair to add to your collection. With a wide selection of MEN'S BOOTS available at Cheaney, it can be a hard decision to make. Explore more styles online now, including BALMORAL, DERBY, and many more styles on offer.

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