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How To Wear Boots – An Essential Men’s Fashion Guide

Boots are a winter footwear essential. In the cooler and wetter months, knowing how to wear boots will give you a step-up in your weekend wear and a leg-up in the office. Plus, you’ll be protected against the weather – be it, rain, wind or snow.

From the Chelsea to the hiker to the renegade biker, boots for men are about to get simpler. We’ve broken down the manufacturing and construction, sole types and different boot silhouettes, before moving on to some boot-ilicious style tips.

Why Welt?


Good quality boots are welted. Welts are the pieces of leather where the sole of the shoe attaches to the upper leather. Most cheaply made shoes don’t have welts – the sole is cemented directly onto the bottom of the upper – and when the sole wears down the shoe has to be thrown out as well. Boots with welted construction, however, have their soles stitched to the upper so a cobbler can easily replace the sole. And your boot lives on.

Blake welting is the simplest and cheapest welt. For a blake welt, the upper is wrapped around the insole and attached between it and the outsole. A single stitch attaches everything together. These soles are more flexible and result in a more affordable boot due to it being less labour intensive to make (always done by a machine).

Goodyear welting is the most labour intensive, durable of the three methods of construction. It can be done by machine or by hand and involves multiple steps. The two-level stitching makes it incredibly easy to resole a goodyear welted shoe.

Got Sole


Below are the most common welted soles, to help you navigate boot world:

Commando: This is your classic hiking/work boot rubber outsole. Known for its thick, traction-tread, the commando sole offers supreme grip and is weather resistant. But it does give back a chunky profile.

Wedge: This sole reflects mid-century workwear. The wedge sole combines traction and stability whilst remaining lightweight. Short in stature? These soles create a couple extra inches of height too.

Crepe: These rubber soles are milky yellow in colour, crinkly in texture, and are slightly heavy to wear. The rubber is sourced directly from the rubber tree or made synthetically.

Leather: The original sole, leather is primarily used with dress boots as it has the lowest profile, neat and chic. But, it’s also the least weather resistant, not the best for trudging through water or snow. They do make a satisfying tap noise as you walk. Click, clack.

Boot Types


#1 Derby boots are like their dress shoe counterparts. The Derby distinguishes itself by its laces: eyelets stitched on top of the shoe vamp, creating an open front. They are a dress boot and come with smart leather soles and should always be welted. Colours mimic those of derby shoes: tan, burgundy, black and brown.


#2 Chelsea boots were made famous by London rockers (The Beatles) and English cool cats in the Sixties. Then, cowboys took the reigns, drawn to the boot’s elastic trunk construction – a slip-on-and-off ease. It’s cousin is the jodhpur: an ankle style with a rounded toe and a low heel, fastened with a strap and buckle.Today, the Chelsea comes in buttery calfskin, touchable suede and smooth cowhide, in an array of colours – tan, brown and black.

boots#3 Brogue boots are an adaptation of the dress shoes with the same name. Essentially, take a leather dress boot, add decorative stitches, perforations and serration across the top – to stop water build (we’ve been told), and you’ve got brogues. Top of the range brogue boots come in handcrafted leather, a long-wing punched brogue detail and goodyear welted (perfect with a suit) or with a wedge sole for smart casual weekends.

boots#4 Desert or chukka boots are named after a period of play in polo, the ‘chukker’. Traditionally made in suede or calfskin uppers, the desert boot typically boasts a crepe rubber design inspired by footwear made for British Army officers in Egypt. For a dressier style, opt for a leather sole, perfect with smart jeans or chinos.

boots#5 Worker boots stem right back to the US depression as well as the two World Wars. So, they’re sturdy, durable and hard yakka. Today, worker boots are as strong as ever with commando soles and provide protection with thick hide. But there’s an emphasis on style and comfort (some with a wedge sole), coming red and blue colourways and contrast laces for refined, heritage-inspired style.

boots#6 Hiker boots have the capabilities to scale mountain terrain. But for men’s fashion they need to be aesthetically appealing. These day hiker boots come expertly crafted from premium leather, with a focus, comfort and durability, especially when soled with a rubber sole, rippled for extra traction.


#7 Biker boots aren’t just for the motorcycle rebels. Inspired by icons Marlon Brando and Steve McQueen, this boot rides well in today’s wardrobe: black leather, ankle-hugging trunk and a chunky leather sole. Metal hardware comes via

Bottoms Up

When wearing the boot, what pants go with which boot? And how do you style them exactly? To dress up a boot, wear the pants down past the ankle. To the onlooker, you’re wearing a dress shoe, with a slightly sturdier sole. For a more casual look and to show off the boot, cuff the pant hem (or invest in a pair of cropped trousers). Read on for a style guide, with common pant options.



The style of jeans varies, which affects your boot-game. Ripped and washed out? Opt for a slim-fit and don a pair suede chelsea boots or built-to-last biker boots, which make the perfect match for any dressed-down look.

Selvedge or mid-blue wash jeans look great with heritage worker boots or the adventurous hiker. Try neatly cuffing the denim hem to expose the mechanical vamp and eyelets.

Casual Trousers


Casual cotton trousers – from chinos to jersey jogger pants – get a style lift with boots. For a quintessential gent outfit, try pairing a heritage harrington jacket and neutral chinos – cropped for a fashion-edge – with classic English desert boots in buttery tan.

For the athleisure-lover, take tapered joggers in black and worker or hiker boots with a rubber-wedge sole, tucking the cuffed ankle into the boot, for a space-age look. Just add a bomber jacket or neat, lightweight hoodie to complete the sportsluxe style.

Smart Trousers


To be ‘suited and booted’ never felt so real. And you have some stylish options. Smooth, silky leather Derby boots  – with a slim-leather sole – for a sleek profile are the perfect boot for woollen trousers, teamed with a matching tweed blazer and plaid knit for heritage tailoring.

While the Chelsea boot in dark brown is a perfect work suit boots, try the traditional jodhpur boot, in soft calfskin and delicate metal buckle.



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