Men’s boots have come a long way since hoedowns and hiking. From Chelseas to chukkas, there’s a whole wide world of options out there to play up your favorite outfit.
The Chelsea Boot
Characterized by ankle-high height, a close fit and, most notably, no laces… the Chelsea boot employs an elastic panel known as goring, which allows the shoe to stretch when taking it on or off. The shoe first came about during the Victorian era as a riding boot praised for its convenience and later re-emerged with the Beatles in the 60’s.
How to wear them: More refined varieties with dress shoe soles are making a comeback which can be perfectly paired with a slim fit suit. We think its proof positive that suits and boots can live in perfect harmony. We recommend pairing a slim fit navy suit with brown Chelsea boots, like the one pictured here:The Chelsea Zip from
The Chukka Boot
The chukka is also known for hovering in the ankle area. This boot comes with two to three eyelets of lacing and is often outfitted in suede. In the 1940s, chukkas popped up as part of a trend toward casual dressing, and by 1950, the British brand Clarks had invented its iconic desert boots, solidifying the style’s spot in shoe history.
How to wear them: It only takes a solid Oxford shirt and straight-leg jeans with a single cuff that gently covers the Chukka boot(like the one pictured below) to do these shoes justice.

The Chukka from
The Hiking Boot
Hiking boots vary widely in appearance, but generally has a relatively rigid structure that provides support for the ankle without restricting movement. The first hiking boots were likely birthed in the 1870s during the emergence of mountain climbing as a sport in Europe. The shoe has now evolved into the all-purpose outdoor recreation hiking boot we recognize today.
How to wear them: Fortunately, there are now more refined kinds that retain the function and feel of the original without the need for a fleece and a flashlight. Our take is best worn with rolled corduroys (a single cuff will do) and a shawl collar cardigan or fitted Fair Isle sweater.The Lugz Bowery at
The Motorcycle Boot
The height ranges from above the ankle to below the knee, but all motorcycle boots boast a low heel in order to aid in putting the pedal to the metal so to say as well as heavy-duty leather for protection against an unplanned meeting with the pavement. Biking boots are speculated to have surfaced during the Depression era when the Chippewa Shoe Company developed a boot based on those used for equestrian sports in England.
How to wear them: These days, you can flaunt a pair without it coming off like a costume. Toss them on in your downtime with a pair of black jeans, a relaxed-fit pocket tee and, of course, a leather jacket. The Fort at
The Military Boot
Military boots were designed with one goal in mind: to shield you from an unfriendly environment. As a result, combat boots run the gamut from ankle-high to under-the-knee, and are typically made from technical materials. The first boots for battle were worn by the Assyrian army as early as 1000 BC but fast forward a few thousand years, and you’ll find them on the feet of everyone.
How to wear them: Donning dark denim (complete with a couple of cuffs or tucked directly into the boot), a vintage tee and a tailored peacoat with these boots will give your military look some edge.The  Country at
The Winter Boot
Cold weather boots range with styles from military-issue Kevlar lace-ups to suede and shearling-lined slip-ons. They all fit the foot snugly to help retain heat. The first waterproof winter boots made of deer skin and tree bark with bearskin soles are at least 53 centuries old but thankfully the material and structure has changed over the years.
How to wear them: The combination of materials/styles of the winter boot allows you to comfortably keep them on throughout the day with jeans, a thermal Henley and fitted puffer coat.The Ratchet found at


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