Boots always seem to get more done than shoes. While shoes are busy arguing semantics in a boardroom, boots are out in the garage welding shit. Shoes spend their weekend shanking golf balls while boots are going over, around and through every surface on earth. Truth is, shoes were for buzz-cut boys playing acoustic guitar until boots and mop tops came over from England and started a revolution. Boots have long belonged to the movers and shakers of history, and dammit if they’re not going to keep going. Eight types of boots, three choices each. Hop to it.
The Chelsea Boot
Chelsea boots began life in England in the mid-19th century and didn’t stray far from home until recently. The elasticized wonders were a staple of the mid-’60s mod scene and protected the feet of seemingly every British invader from John to Ringo. Recently they’ve seen a revival on many of menswear’s best dressed.
Who to Channel: those four Liverpudlians
Pairings: anything from denim to suit trousers (just keep things tapered at the ankle); a ravenous fanbase
Declan Chelsea Boot by Grenson $275
Suede Chelsea Boot by R.M. Williams $495
Newmarket Suede Chelsea Boot by Edward Green $1,470
The Ankle Boot
Boasting a higher degree-of-difficulty than the Chelsea boot, ankle boots might be the coolest footwear ever made. They’ve graced the feet of rock stars, played their fair part in creating a few illegitimate children and complimented the tightest pants mankind has had to offer for decades.
Who to Channel: Keith Richards; that guy down the street who had a Trans-Am and wore a leather jacket with a bandanna hanging out of his back pocket
Pairings: a fuck-you demeanor; if you’re going to wear leather pants, now’s the time
Chris Inside Zip Boot by Frye $328
London 20 Jodhpur Cropped Boot by Saint Laurent $669
Pebble-Grain Zip-Up Boots by McCaffrey $745
The Wingtip Boot
You got formal embellishment on my casual footwear! You got casual footwear on my formal embellishment! The wingtip is dressed up enough to be worn with a suit and casual enough to end up under denim or a pair of cords.
Who to Channel: that oddly stylish Philosophy 210 professor
Pairings: corduroy, wool, denim — and just about anything else you can think of
Dalton Wingtip Boot by Allen Edmonds $445
Stow Suede Brouge Boot by Tricker’s $670
Leather Wingtip Brogue Boot by Thom Browne $1,275
The Chukka Boot
About as casual as all-leather boots get, the chukka (or desert) boot was first worn by British soldiers in Africa during WWII. Afterward they made their way across the Atlantic, becoming a casual staple for the second half of the 20th century and still gracing the feet of stylish men in the cooler months. Clarks made the originals, but upmarket offerings only improved on the formula.
Who to Channel: McQueen, Newman, any other guy from the ’50s you see on The Impossible Cool
Pairings: a quality sweatshirt and a game of post-Thanksgiving touch football
Desert Boot by Clarks $119
The Newman Chukka Boot by Paul Evans $339
Suede Chukka Boot by George Cleverley $700
The Hiking Boot
We’ve kept a respectable distance from technical boots, but the best pairs of old-school hiking boots boast the same alpine prowess that made them popular in the first place along with a great look.
Who to Channel: alpinists, men with rolled-up wool hats
Pairings: a thick sweater; a beard, unkempt
Ripple Sole Scarponcino Boot by Fracap $249
Mountain Light Cascade Clovis Boot by Danner $449
Military Hiker Boot by FEIT $800
The Hunting Boot
For actual hunting you may want something more technically advanced, but the duck/bean/Maine hunting boot is a staple in the Northeast and has ensconced the feet of everyone from Hemingway to Thad in Sigma Chi. They may not be as warm or as waterproof as some others, but Ernest would probably tell you to sack up.
Who to Channel: a yeoman after some pheasant
Pairings: golden retriever, waxed-cotton jacket
The Original Duck Boot by L.L. Bean $119
5-Inch Dress Hunt Boots by Yuketen $695
Mid-Folk Leather Boots by visvim $1,005
The Work Boot
Strong, long-lasting and just stylish enough to stay on your feet for most of the colder months: that’s all a work boot really needs to be. Little wonder that the design was more or less perfected half a century ago.
Who to Channel: those guys eating lunch on an I-beam atop the Empire State Building
Pairings: grit, tough denim
Blacksmith Oil Tanned Boot by Red Wing $300
1000 Mile Boot by Wolverine $400
Zermatt Suede Boots by Visvim $1,030
The Trench Boot
Worn since WWI, the trench (sometimes called army or officer) boot is a handsome staple that’s shaken its military roots and manages to look a bit more cleaned up these days than it did stomping into Flanders.
Who to Channel: the Great Escapees
Pairings: rolled denim, trench foot
Kenton Cap Toe Boot by J.Crew $250
Indy Boot by Alden $530
Service Boot by Viberg $720
The Cowboy Boot
Like many Americana wardrobe staples, cowboy boots are rooted in function. Pull them on, wear them hard and use them for years. There are two mains styles: traditional cowboy boots that feature a riding heel (taller and angled) and roper boots that have a shorter heel, designed to handle a day of walking.