Clockwise from top left: Andrew Marc Dorchester canvas and leather Chukka boot, $178 at Neiman Marcus; Ralph Lauren 'Jayden' leather outdoor boots, $595 at Saks Fifth Avenue; Red Wing Beckman Round, $340 at Red Wing Shoes; Cole Haan Lionel dress boot, $348 at Cole Haan.

As we dive deeper into November, the weather begins to change and temperatures plummet into chilly lows. The season of summer has been put to slumber and it is no longer is it acceptable—or practical—to walk the streets in summer footwear. It's time to retire those favorite espadrilles and your old faithful suede loafers.

Instead, I insistently suggest that you switch it up for something more seasonal: the boot. Boots have come a long way from the feet of construction workers to the feet of dapper gents the world over.

There are only three things you need to you ask yourself when choosing a pair of boots. 1) Are they practical? 2) Do they enhance my personal aesthetic? and 3) How are the fit and comfort? Their versatile nature will mean that they will grant safe passage through winter well past the new year. Once you own a well-rounded pair it won't matter whether you take a leisurely approach to dressing or leave the house dressed to the nines. Boots are undoubtedly a winter staple, so suit up and boot up and march on out into that winter wonderland.

  

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