The Boot Guide for Men: Fall & Winter 2016

Preface: Originially, I wrote this post in 2013, but most of the statements in this post are just as true now as they were then, so I thought I’d share it once more. Only minor adjustments and additions have been made.

The Chelsea Boot

These are the winter equivalent to the socks-in-sandals predicament that we can’t seem to get away from summer-in and summer-out. (If you’re at all confused by the reference, or you are an offender of this fashion faux-pas, take it from a native Floridian, the short answer is: don’t do it.) They’re not dressy, nor are they casual — perpetually trapped in an awkward limbo of wasted cowhide. Unless you’re a rich, pretentious, Hampton-dwelling investor, stick with any other style. Women, however, can pull these off — with a normcore minimalism, a grungy flare, a little urban-preppy action, or even some modern mix of the three (boho-normcore-something ;) — and knock gents and ladies alike dead with them.

The Biker Lace-Up Boot

For most, they’re overdone. These things are cumbersome and come studded out with metal garnishments usually polished chrome but occasional (and more recently) matte black. They’re stylized with embroidery of darkness & devils or screaming with American pride — Bald Eagles and all. Others are more toned down or austere — offering none of the embellishments, but all of the utility and dependability most come to expect.

For those of you that relish the idea of afternoon hikes in the desert, romantic walks on the brisk beaches of Coney Island, hopping a train for barhopping the East Village, or meeting a friend for coffee and a walk on the Highline, these are the ones for you. Tucking a pair of skinny jeans inside and layering sweatshirts & scarves beforehand make these boots the way for your outfit to look relaxed, and just the right amount of put together without overdoing it.

The Chukka Boot

Unseasonably warm day? Heading for brunch in Astoria? Toss on a your fave pair of jeans — cuffed. Maybe a quirky pair of socks if you’re the type and that casual blazer over a sweater for that chill, hangover-recovery look. (Because we know how hard you went last night.) Grab your messenger bag and that new camera of yours you’ve been dying to use and get going — your friends are already three mimosas deep!

The Harness & Engineer Boot

Some of us are more driven, more pragmatic, hard-workers that are up at four in the morning on Saturday while the rest are still sleeping off Friday night, prepping for those aforementioned mimosas. While its not that these don’t have a place in city life, (Dallas & Atlanta, I’m talking to you!), but the vibe they’re sending is that of a Midwesterner persuasion. A good fashion analog would be Levi’s jeans: these styles are the 501 Original of the boot sphere. If you’re willing to pull these off, you’re that quirky friend that every group needs a dose of.

The Cowboy Boot

Much like the Harness and Engineer styles, the Cowboy boot exudes a sense of responsibility. Unlike the Harness or Engineer, this style has a spunkiness to it and is much more versatile. It just screams classic Americana and fun. Seen in big cities to small towns; dusty Midwest ghost towns to East Coast beach towns. Perfect untucked to match your favorite NFL team’s jersey or tucked with a more dressy outfit like a stone wash jeans and a sweater or that cozy denim chambray shirt paired with white denim jeans. White denim in winter though, you ask? No doubt, says Alexander McQueen. Don’t question the master. Chances are its not snowing and it looks like fall all winter long where you live, so why not do those boots a justice by highlighting them?

All in all, you can’t go wrong with choosing a boot, because any boot will do for your look what a sneaker cannot during these seasons.

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