8 Pairs of Boots to Kick Winter’s Keister With

Chances are if you live anywhere snow falls, your winter boots are looking pretty beaten up right about now. From the salt stains, to the water affected leather, to the worn down outsoles, we know we’ve put our boots through hell this polar vortex. While we do recommend you buy for quality and take care of your footwear, a new pair of the everyday winter essential can be just the inspiration you need to see out the rest of the dismal, dreary cold.

And if you’re lucky enough to live in a place where winter isn’t as soul-destroying as it has been here on the North-East Coast, there’s plenty of suede on the list to keep you from missing out on your last footwear re-vamp until spring.

Red Wing 8890 Moc Leather Boots


Featured a few times in our best-of-Pitti Uomo roundup, Red Wings are a tried-and-tested ol’ reliable when it comes to heavy duty boots. The iconic workwear brand still manufactures all of their high quality footwear in the US, and with their headquarters in Minnesota. I’ll take their word that they’ll last the winter. (Tip: take a style cue from Red Wing owner Mr. Ryan Gosling and don’t be afraid to keep them on as the weather warms up as well.)

$285, Buy now at Mr Porter

Timberland Men’s 6″ Collar Boot


Timberlands are an extremely popular winter boot choice for men, and for good reason. Not every winter boot can boast a waterproof guarantee for their leather uppers, and as much as we love a good pair of rain boots, those just aren’t a warm enough option for when the temperature gets into the negatives. The simple, sleek design of these black nubuck Timbs are versatile enough to go with pretty much any casual outfit, and as we’ve veered away from the classic “wheat” brown colourway, this more modern variation will also hopefully save you from anyone calling you “deadass.” If you don’t know what that means, congratulations. Save yourself the time and confusion.

$175, Buy now at Amazon

Frank and Oak George Suede Chelsea Boot


What kind of menswear authority would we be if we didn’t include a pair of suede Chelsea boots in this article? One that’s not cliche, I guess, but over the past few years it’s been nearly impossible to ignore the influx of stylish Chelseas that seemingly every store is carrying now. We promised suede on the list, so here we are, delivering with a great, simply designed light brown suede Chelsea with a casual crepe sole at a price that will make you think twice about splurging on those Common Projects.

$169, Buy now at Frank and Oak

Moncler Peak Pebble-Grain Leather Hiking Boots

Now, enough day dreaming — it’s time to get real again and look out the office window. If the snow plow companies are still making a killing and going down your street twice a day, suede is a little premature. These Moncler pebble-grain leather boots modelled after the legendary Danner hiking boots will help you traverse snow mounds of any size with the help of their thick Vibram soles, whether that’s while you’re out for a hike in the countryside or trying to hike over the knee-high snow banks on the side walks.

$863, Buy now at Mr Porter

Sperry Wahoo Suede Chelsea Sneaker


If you looked out of your office window and realized the worst of winter you’ve experienced this year was your in-laws’ Christmas quiche, then boy, have I got some more suede for you. I’ve said it before: everyone and their Mum have been making suede Chelsea boots for a while now, but these suede Chelsea sneakers from Sperry stand out from the crowd with their Vans-like rubber outsoles. The elastic side panels make this shoe super comfortable and casual.

$100, Buy now at Sperry

Sperry Gold Cup Leather Crepe Chelsea

Also from Sperry, another Chelsea boot (gasp!), but this time, in a full-grain black leather upper. More refined and elegant, this boot’s tidier upper and sleeker last allows you to dress this boot up more than their other Chelsea, while retaining comfort by using a crepe sole on the bottom. With a welt construction holding the upper and outsole together, the price not only justifies itself, but looks like a pretty good deal, too.

$300, Buy now at Sperry

Tricker’s Stow Burnished-Leather Brogue Boots


On the subject of versatility, this Tricker’s exclusive to Mr. Porter is probably the easiest to dress up or down out of the entire list. With each section of the boot being hand clicked, stitched, finished, and welted, they’re well up there amongst the highest quality boots you can get, too. Dress these down with a pair of jeans (or for that English countryside look, a pair of Harris tweed trousers), or dress them up with your winter weight suits. This shoe goes from dress boot to dog walker without having to undo a single eyelet, thanks to the dark brown colour and wingtip brogueing.

$595, Buy now at Mr. Porter

R.M. Williams Craftsman Leather Chelsea Boots


Toning down some of the formality while keeping a similarly sleek silhouette and versatile identity, we’ve brought you — no points for guessing — another Chelsea boot. Aussie brand R.M. Williams has been around forever, however. Think of them like Blundstone’s younger, more refined, and more stylish brother. The brand from Down Under delivers a nicely chiselled toe box while also utilizing Goodyear-welt soles that ensure you’re able to keep resoling and resoling the upper when you’ve worn the bottoms down — that is, assuming you keep the yearling leather in good enough condition.

$440, Buy now at Mr Porter