Keep your look on message while keeping your feet safe from the elements with this selection of stylish, durable yet presentable boots.
Oxfords and Monks don’t go with everything, and tassels should be found on strippers, not loafers. During Hong Kong’s colder months lace up with a sturdy yet stylish pair of chukka boots – versatile, leather ankle-length boots that come in a wide range of style and looks.
In fact, it could be said the humble chukka boots is a man’s best friend during the winter months, when you can’t risk loafers due to weather and need something that comfortable transitions between outdoor adventures and indoor style. They also come in a wide range of finishes meaning you can lean formal or casual.

Timberland’s Heritage LTD Waterproof Chukka Boots are made with a double membrane of bark-hued premium eurobeg leather to ensure dry feet and a rugged look. Designed with anti-fatigue technology for maximum shock absorption, as well as a three-eye lace up front, these boots will make style look like a walk in the park.

Complete your understated classy look with a pair of George Cleverley’s Nathan Brown Calf Chukka Boots, part of the brand’s ready-to-wear line. Handcrafted in England with a three-eyelet lace-up setting the scene for a plain yet elegant leather front and linings, there’s also Goodyear-welted soles for the ultimate grip and walking ease.

Clarks Atticus Limit chukka boot features an elegant profile that’s both modern and timeless. With a full grain leather sockliner that feels velvety soft, a surprisingly rugged exterior, and impact-absorbing OrthoLite footbed, these chukkas look just as good with a pair of jeans at a BBQ as they do in the meeting room.

The Scout by the Thursday Boot Co is a chukka for a new generation. Blending classic British style with bold American aesthetic, these boots combine Brown Thursday Chrome leather with a full-glove leather interior lining, premium round wax laces, stitch out construction, and a cork-bed midsole for ultimate comfort and support. You’ll also have the traction of an F1 car thanks to studded rubber outsoles.

Whether you’re out for brunch with the missus or planning something outdoorsy with the boys, the durable textured crepe rubber soles of the Ogden Stitch Chukka from Cole Haan have you covered. With rich leather and suede uppers and partial leather lining, these striking boots can transform through the day as quickly as you can. Dapper kicks for a dapper man.
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