Online Shopping Picks: Best Men’s Winter Boots

Pick a boot, any boot. Back left corner: Wolverine 1000 Mile in Navy Suede. Back right corner: Timberland Britton Hill Waterproof Moc Toe. Center: Timberland West Haven Chukka. Front left: Thursday Boot Company Chocolate Suede Scout Chukka. Front right: Thursday Boot Company Roughout Captain Boot.
Pick a boot, any boot. Back left corner: Wolverine 1000 Mile in Navy Suede. Back right corner: Dr. Scholl’s Burke Boot. Center: Timberland West Haven Chukka. Front left: Thursday Boot Company Chocolate Suede Scout Chukka. Front right: Thursday Boot Company Roughout Captain Boot.
Welcome to our first Online Shopping Picks post of 2016! The extremely gradual change of the seasons this past fall & winter has left me a bit caught off-guard stylewise – as soon as the calendar hits late September and early October, I’m normally all about wearing sturdy denim, thick cardigans and tough boots whenever possible, on through December and January. But the fairly temperate climate in NYC made it somewhat difficult to do that when compared to previous years – I still have yet to see snow in NYC, an oddity for me considering cold winters growing up in Michigan. If you find yourself in the same situation, rest assured – winter will get here soon enough, likely with a vengeance. And when it does, make sure you’re prepared ahead of time with a standout pair of reliable winter boots. The picks that follow here were selected by yours truly for their combination of versatility, functionality and overall style. So you won’t find any steel-toed boots or extreme hiking boots below – just reasonably rugged, tough pairs that can work going into the office, going out after and maybe doing some light trekking off-road on the weekends. Check out these picks below, and let me know if I missed any!

#1. Jack Erwin Chester Captoe Boot — $220

A lovely shade of dark brown and a refined captoe merge with a hand-stitched rubber outsole.
A lovely shade of dark brown and a refined captoe merge with a hand-stitched rubber outsole.
The Chester Captoe Boot as seen here checks off three key boxes in rapid succession – great looks, a really solid price and that crucial rubber sole. Jack Erwin has been doing a great job releasing well-curated collections by the season (Exhibit A: its loafers), and its boots are no different. The captoe makes this pair sleek and office-ready like a dress shoe, particularly in the Espresso color, while the rubber sole can definitely get you where you need to go this winter. It’s likely the next step up pricewise from other picks, but well-worth it.

#2. Thursday Boot Company Brown President Boot — $199

No captoe, but still a relatively slim profile -- the President Boot from Thursday Boots.
No captoe, but still a relatively slim profile — the President Boot from Thursday Boots.
Whereas the Jack Erwin captoe is fully suit-ready, the Thursday Boots President Boot is a little more business-casual thanks to the slightly lighter brown leather and lack of a captoe. But that doesn’t make it any less sleek – it’s still got a slim toe shape, yet the rubber sole you’d expect from a durable winter boot. If the sole is anything like that on the Roughout Captain Boot or the Chocolate Suede Scout Chukka, it should provide great traction while holding up reasonably well. These can definitely be worn with a slim pair of denim and a navy blazer-chambray shirt combo as part of a daily uniform – throw in a sharp V-neck sweater if it gets cold.

#3. Wolverine 1000 Mile Boots in Navy Suede — $360

The Wolverine 1000 Mile Boot in Navy Suede, in person -- a Style Guide favorite.
The Wolverine 1000 Mile Boot in Navy Suede, in person — a Style Guide favorite.
The classic 1000 Mile silhouette gets a suede-centric upgrade – which also bumps up the price and knocks it a bit further down this list. However, these Navy Suede boots are true beauties – the suede feels smooth & rich, and the sturdy construction lives up to Wolverine’s standard. The profile is fairly slim as far as a boot goes, so these have looked right at home even alongside dark blue denim. I’d also recommend you try these out with light grey chinos, which should really make that navy suede pop. The price is going to be an investment that merits proper care, so they might be less ready to wear in all kinds of weather – but it’s going to be hard to leave them inside.

#4. Cole Haan + Todd Snyder Olmstead Boot in Chestnut — $249

Certainly more unique-looking, and perhaps more suited to casual wear, but still a durable and stylish option.
Certainly more unique-looking, and perhaps more suited to casual wear, but still a durable and stylish option.
The Olmstead Boot is marked down to $249 from its original price, so it’d be a wise bet to jump on them now (sizes are somewhat limited, too — from 8.5 up to 13, pushing it further down the list). They’re perhaps the most unique-looking pair of boots on this list owing in part to that wedge sole – they’ll likely wear a bit more like the sneaker-boots that seem to be all the rage. The moc toe silhouette and contrast stitching could make these a bit more tough to pull off, but the dark brown color grounds them a little bit. That should help them sit just right underneath slim grey or blue denim in a casual workplace. Pair these guys up with a navy crewneck sweater and slim tan chinos on the weekends, too – trust me.

#5. Red Wing Heritage Iron Ranger Boots in Black — $319.99

A sharp Black makes these a tad more refined than the thicker profile might suggest.
A sharp Black makes these a tad more refined than the thicker profile might suggest.
One of the most recognizable boot silhouettes in the game today, the Iron Ranger is another certified classic. It wears a little more bulky than the sleek Jack Erwin or Thursday pairs at the top of this list, and it’s pricier, so it does get knocked down the list. BUT, the black color makes this pair both rugged and fairly refined – they’re going to be that pair you reach for in extremely deep snow, yet could still leave on for work if you take care of them properly and match them up with the proper style essentials (like sturdy chinos or denim and a refined chambray shirt). Like the Wolverine boots above, these guys are a definite investment – but as investments go, it never hurts to stock up on tough boots before winter.
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So that brings us to the end of this list – know that some other budget options were considered, like the much-loved JC Penney Stafford Deacon Wingtip Boot. I’d also urge you to swing through the seemingly ever-expanding footwear offerings at J. Crew – they stock a variety of boots, including the classic Alden Indy, and sometimes offer them up on sale. It might seem as if there’s plenty of time before winter really hits – but it’ll be here before you know it. So stock up on your favorite boots, and wear them well this winter.

Tell me – what pair are you thinking about buying on this list? What’s your winter boot go-to right now?

Florsheim

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