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

Online Shopping Picks: The Best Men’s Winter Boots

Editor’s note: Click this link to read the 2016 edition of this site’s best men’s winter boots.

So these past few weeks in NYC have delivered some of the coldest weather on record — not only in the city itself, but across much of the rest of Eastern U.S. and Midwest. That really puts things in perspective style-wise, because in cold weather like this, function is just as important as fashion, particularly in the footwear department when trekking through feet of snow (or even just walking through blustery, chilly winds). There are several options on the market that serve only functional purposes (like the famous Bean boot from L.L. Bean), but the best boots serve both stylish and utilitarian means — like the 5 picks below. Read on and leave your picks for your favorite pair at the bottom!

#1. Wolverine 1000 Mile Boots in Brown — $360

An all-American original with rugged details.

An all-American original with rugged details.

Wolverine’s 1000 Mile line of boots is an all-time classic — revered for their durability and toughness, the brand has slowly built up a fashion following across the past five or so years as workwear and Americana themes have come back into vogue in men’s fashion. While this pair is particularly pricey compared to options you might pick up on a budget, the price is well worth it —the 1000 Mile collection combines toughness and dependability with beautiful leather styling and lots of attention to detail (read more on a pair from the line here). In a rich brown color like the pair above, they’ll work at the office with more rugged outfits as well as marching through the cold to get there. Note that these boots are also on-sale through Nordstrom for a bit less than the above price.

#2. Thursday Boots Captain Boot in Brown — $199

A slimmed-down silhouette compared to the 1000 Mile boot, for far less cash.

A slimmed-down silhouette compared to the 1000 Mile boot, for far less cash.

The second pick on this list drops the price down significantly from the Wolverine boots above, without losing too much quality. In fact, for being a very new startup courtesy of Kickstarter, these boots provide just as much top-notch styling potential as any other boot from the heritage brands on this list — and they do it for a greatly reduced price.  They offer a slightly sleeker-looking silhouette, a more office-friendly captoe and that same rich brown leather that should pair well with all kinds of outfits throughout the winter. And even more importantly, the company’s garnered some positive reviews around their initial collections, meaning it’d be more than safe to take the plunge on this pair.

#3. Frank & Oak Rubber-Soled Italian-Leather Lace-up Boots in Black, $175

From Frank & Oak's new footwear line — the sharpest pair on the list yet.

From Frank & Oak’s new footwear line — the sharpest pair on the list yet.

The first pair of black boots on this list is also, quite curiously, on-sale through Frank & Oak with plenty of sizes left. On top of that, they’re by far the cheapest pair on the list to date, yet if F&O’s other new footwear offerings are any indication, this pair should deliver in both quality and looks. They’re by far the dressiest pair on the list, given that sharp black color (a slightly resurgent footwear trend), and the brushed black eyelets and waxed cotton laces only add to their sleek styling. These would work best in the same manner that Bond wore his black dress boots in Skyfall — with a sharp grey suit or tailored navy trousers or cords. They’d also work to channel your inner Justin Theroux with slim dark denim. Given the rate of turnover on Frank & Oak’s site, the question remains as to how long these boots will stay in-stock, especially on-sale.

#4. Red Wing Beckman Boot in Black Featherstone — $340

Red Wing boots combine heritage craftsmanship with rugged styling potential.

Red Wing boots combine heritage craftsmanship with rugged styling potential.

Yet another pair of black boots fills spot #4 on this list. Just like their Wolverine brethren, Red Wing has a long heritage of delivering sturdy boots made to last. This pair of Beckman boots knocks down the price compared to the 1000 Mile pair listed above, but that in no way detracts from the quality. These have that same reinforced sole and Goodyear welt construction that should make resoling possible down the line — practically like getting a new pair of boots for far less than full price. And in this case, the bottom sole is stitched to the midsole, meaning these boots can more than stand up to the abuses of winter weather. Notably, the leather on this pair is richer in color than your typical black leather — it has a luxurious, almost burgundy-like tint to it. Throw ’em on with dark denim, a henley and a shawl cardigan or pair them with slim burgundy cords and a crewneck sweater.

#5. Florsheim Gaffney Wingtip Boots — $150

A wingtip option that combines tan leather with a grippy-looking sole.

A wingtip option that combines tan leather with a grippy-looking sole.

The final pair on this list is the first and only set of wingtip boots on here —mainly because of the fact that while inherently stylish, incredibly nice wingtip boots (like the Allen Edmonds Dalton) don’t always do the best job of beating back the snow and slush. If you have a pair in your closet though, give them a try — after all, $400-plus boots don’t deserve to just sit around! The Florsheim Gaffney is a slightly more upscale replacement to JCP’s much-loved Stafford Camlin and Stafford Deacon wingtip boots, but in a louder “toffee” color. That makes them a little more eye-catching and slightly less versatile than the darker brown options on this list, as tan doesn’t necessarily sit as well under, say, khaki chinos or dark charcoal trousers. They would, however, pair just fine with dark denim and navy chinos, for example. And the sole on these boots looks to have a fair bit of grip as well, which is a definite positive for stepping outside in these chilly temperatures. The leather also looks to have some texture, a nice way of adding a bit of visual interest to fall and winter outfits.

Although many of these boots are up there in price, the benefits are well worth the extra dollars, as a great pair of boots can combat slush, snow and ice without needing a change for working hours — or dinner and drinks out later.

Got a favorite pair of winter boots? What other options would you add to this list? Leave it all below! 

Additional note: Look for a Reader Giveaway Opportunity coming up on the blog! I’ll be giving away a Linjer Leather Goods wallet! Details coming on Wednesday. Thanks for reading! 

 

What to Wear Today: Braving the Cold

Editor’s note: Occasionally, this site will cover what you should (or could) feasibly wear for specific situations, outside of holidays and other big events — consider this a combination style suggestion and a look into the author’s personal wardrobe.

Ready for the cold weather (hopefully). Scarf by J. Crew Factory. Overcoat by Kenneth Cole. Gloves by Target Merona.

Ready for the cold weather (hopefully). Scarf by J. Crew Factory. Overcoat by Kenneth Cole. Gloves by Target Merona.

Today (at least in New York City and across much of the rest of the country), it’s winter in full force. A huge winter storm hit a large swath of the country earlier this week, and while NYC was lucky to escape major snowfall, we’ve got some snow on the ground here now. Given that, it seemed as perfect a time as any to break out the below boots — a thick, sturdy, dependable pair of Wolverine 1000 Mile Austen boots in a utilitarian black (for a full review of the boots, head here). Combined with some other winter-centric touches as outlined in the above photo, I’m all set for today’s cold weather. Reaching for a similar combination, if you work in an office, should keep you warm from car to office, or subway to office, or from the bus to the office … you get the drill.

As reviewed: Wolverine 1000 Mile Austen boots in black. The perfect shade and style for a winter day like today.

As reviewed in 2013: Wolverine 1000 Mile Austen boots in black. The perfect shade and style for a winter day like today.

A thicker coat (potentially with an added zip-up implement, like this Kenneth Cole option pictured) could add some extra warmth while also maintaining a streamlined silhouette. There are other great ways to stay stylish and warm in the cold weather, too. Thicker textures like chambray stand up well to chilly temperatures, and layering with a shawl cardigan or v-neck sweater (I’m personally wearing a beige J. Crew Factory v-neck sweater today) could also do the trick. If you feel a hat is warranted, there are plenty of cheap options out there from, for example, H&M.

And when wearing sturdy boots like the thick ones above, some slightly heartier ribbed socks would also fulfill two functions — keeping your feet warm and fitting in stylishly with other portions of your outfit. Above all, do your best to stay warm — but keep some style ideas in mind for colder temperatures!

And in other slightly related business, keep your eyes open for an upcoming giveaway opportunity in partnership with East Dane. This post should be hitting on the site within the next two weeks!

What are you wearing in today’s chilly weather? Any further style tips or suggestions?