As winter starts threatening to rear its ugly head, things are about to change, wardrobe-wise. For the women, their looks are about to be replaced by Duvet-esque outerwear, but guys have plenty of options in autumn/winter styles.

Depending on where you are from, footwear can be one of the most important articles of clothing during the cold months. Yet, most of us wear the same kicks all year round, when a proper pair of boots may be more appropriate. For many guys, they stopped wearing ankle-length boots the minute they start high school, when mom does not have quite as much pull in the clothing sweepstakes. There is, however, usually a point in time after university where one realizes that a pair of Skytops are not proper substitute for a pair of chukka boots.

With that, we thought we’d show you some of Selectism’s favorite boots this season and maybe even share with you what we’re wearing them with.

Read and view more on our favorite winter boots of 2011 after the click.

Buttero Hiking Boots

This should come as no surprise to frequent readers of Selectism, but these are just too beautiful not to mention again. Hand-made in Italy, featuring suede uppers, sheep wool lining, contrast leather heels, and plenty of other well thought out details. These weekend warriors will bless any pair of denim they are paired with.

Gucci Leather Mountaineering Boots

Simple and smooth, these hikers are like Johnny Jewel, screaming Italians Do It Better. Glossy enough that they scream catwalk as readily for a trail walk (especially with the ubiquitous Gucci red and green on the laces), they’ll take you to from the park to the office in no time (assuming you’re a creative, with a houndstooth blazer and acne skinnies office dress code).

Sperry Top-sider A/O Chukka Oil Cloth

Sperry’s have been on the takeover for the last few years, from Brooklyn to Bal Harbour. Looks like the illegitimate child of a boat shoe and a chukka boot, yet somehow is still completely balanced.

Bottega Veneta Calf Canvas Ankle Boot

Rock Star swagger meets old-world luxury; Hedi Slimane must be smiling about these ones. Legendary Bottega quality means leather so soft you’ll pet them like a Kardashian (except maybe Khloé). Wear them anytime, anywhere, they’ll bridge the gap from shorts to suits.

George Esquivel Elkhart Boot

It’s tough to choose a winner from amongst George Esquivel’s various bespoke level offerings. Those pink suede desert boots that Waris Ahluwalia seems to live in sure are mouth watering, but I’m going to have to go with the Elkhart, if only because Esquivel refers to it as a work boot for the ‘gentleman craftsman.’ Untouchable, in that ‘make people jealous from across the street’ way. And who doesn’t love that?

A.P.C. Crepe Sole Leather Boots

Trou or jeans, chinos and cardigan’s or power suit, these oxblood leather A.P.C.’s look equally at home in the borough and the boardroom. Get a pair into your weekend bag immediately. They’re like that super-cool roommate (or roommate’s girlfriend) from college: down for whatever.

Jil Sander Hermes Classic

Elegantly functional, these maxi-minimalists prove that subtlety stands out. Another wear with anything,go anywhere, multi-disciplinarian.

Oliver Spencer Brogue Boot

Like that scene in “My Fair Lady” where Professor Higgins is identified as an upperclassman by his footwear (“He’s a gentleman he is, look at his boots.”), ankle length brogues up the class quotient and are about as formal and grown up as a boot ever needs to be. Oh, and speaking of grown up….forget what your boys told you: musicals are gangsta!

Ralph Lauren Purple Label Chelsea Boot

A classic for mods and preppies alike, the Chelsea Boot is extremely versatile, dressing up or down in a heartbeat. It was good enough for John Lennon….

– Quentin Crispy

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