December means that Old Man Winter is knocking at your door. Whether he sneaks up on you or comes crashing in, you need to be prepared with boots that are as rugged and durable as they are fashionable. Here’s a winter boot wish list to help you get a grip this Holiday season.

Timberland Earthkeepers Original 6-inch - men's winter boot guide

Timberland Earthkeepers Original 6-inch


Timberland has been making boots in New England since 1973. Available in Red Brown Burnished or a darker brown they call Mulch Forty, The Earthkeepers Original 6-Inch Boots are a great entry-level boot for the fella who wants rugged style but isn’t ready to throw down a ton of coin for it. The lining is 100% recycled PET, the laces are 100% organic and the rubber lug outsole is made with 34% recycled rubber. Sustainable and stylish.

Red Wing Iron Ranger - men's winter boot guide

Red Wing Iron Ranger


Iron Rangers are the quintessential Made In The U.S.A heritage boot. Shown here in their new Charcoal Rough and Tough leather, they’re also available in Black, Copper Rough and Tough, Muleskinner, brand new Oxblood, and their most popular Amber Harness. They’ve been doing their thing since Charles Beckman founded the company in Red Wing, Minnesota in 1905. If you want to class it up a notch, go for the Brogue Rangers for a wing-tip look. Like most high-end boots, these feature Goodyear Welted construction, which means they’re made to last and can be resoled.

Original Wolverine 1000 Mile Boot - men's winter boot guide

Original Wolverine 1000 Mile Boot


The Wolverine 1000 Mile boot is the dressiest of the collection and look as good with a wool suit as they do with denim. Made of top notch Horween Leather they have a stacked leather outsole and classic welt construction. Like many heritage boots, they are designed to replicate the original design from 1914. There are 8 color and leather choices in the original but several variations are available with slightly different cuts that include cap toes and wing tips. If you want to save a few bucks check out their Since 1883 Collection that pays homage to their company lineage in Rockford, Michigan.

Chippewa General Utility Service Boot - men's winter boot guide

Chippewa General Utility Service Boot


Chippewa Boots were founded in 1901 in Chippewa Falls, Wisconsin. Originally invented for loggers in 1937, they also were worn by the U.S. Army in World War II. Shown here in Cordovan, they are also available in Tan Renegade, Black, and dark brown called Crazy Horse. With Goodyear welted construction the Vibram soles are strong and can be replaced if needed. The waxed laces and antiqued eyelets are pure class. It’s easy to see why Chippewa’s motto is “The Best By Far.”

L.L. Bean Original Duck Boots - men's winter boot guide

L.L. Bean Original Duck Boots


When the snow gets slushy, or the winter rains come pouring down, you may want to keep your nice leather boots at home and opt for the timeless Original Duck Boots from L.L. Bean. These throwback boots from the 1980’s are bigger than ever right now. So much so that they’re backordered by about a month. If you want them this winter you’ll have to order them soon and wait your turn. Makes you want them even more, doesn’t it.

Oak Street Trench Boot - men's winter boot guide

Oak Street Trench Boot


Oak Street is based out of Chicago and uses Horween leathers, Goodyear Welting, and calfskin lining to make their classic Trench Boots. Shown here in Natural, they are available in Black, Brown and Color 8 (oxblood). There are also two rough-side-out leathers, Natural and Brown Waxed Flesh. Multiple sole options are available as well. They’ll hold up to the weather but you’ll have to decide if they’re too nice to wear in the winter slush. We say go for it, that’s what boots are for.

Frye Warren Duck Boot Shearling - men's winter boot guide

Frye Warren Duck Boot Shearling


Frye has been kicking out great boots since 1863 and their Logan Cap Toe Boot is a favorite. If you want something that is a bit more all-weather the Warren Duck Boot Shearling is designed for all-seasons and all-terrains. It’s got a rugged rubber outsole, rawhide leather laces and that classic Goodyear welt construction we keep talking about. It’s lined with soft shearling, which is suede on one side and clipped fur on the other. If you’re looking for a duck boot with a bit more polish and panache, look no further.

Truman Boots - men's winter boot guide

Truman Boots


Based in Pennsylvania, Truman Boot Company is a small company with big ambition. Vince Truman makes the boots by hand in his shop, the old fashioned way. He is a craftsman and an artist that is committed to sustainable tanneries and materials. Truman Boots are the ultimate custom made to order boot; choose from his available leathers and suedes, pull tab, laces, toe design, antique brass or nickel eyelets and lace hooks. Multiple sole options will finish it off. Made using “stitch down construction” they have a leather vamp lining, leather heel counter, leather insole, outsole and a stacked heel. You’ll wait about 6 to 12 weeks for them, but they’ll be worth it.

Helm Marion Olive Blucher Boot - men's winter boot guide

Helm Marion Olive Blucher Boot


Helm is a newer boot company that was started in by Joshua Bingaman in 2009. His passion for classic American boots and Japanese sneakers inspired him to marry durable construction with the detail and design aesthetic of high-end shoe brands. The Marion Blucher Boot is made with Olive Green Horween full-grain leather and a calfskin lining. The mini-lug sole will provide perfect traction in winter snow. Stop by their flagship store if you’re ever in Austin, Texas.

Post written for Cliff Original by Jeremy Lahman.