Style Pick of the Week: Red Wing Heritage Classic Chelsea Boots – The Only Boot You’ll Need This Winter

I’d wager that if you’ve been reading this blog frequently and searching for the best menswear essentials and the best men’s boots, then you don’t need me to tell you twice: The right pair of boots can make all the difference as you deal with winter weather and harsh conditions. If you’ve learned that truth the hard way and could use an upgrade in your boot rotation though, you’ve come to the right place.

Red Wing Heritage Classic Chelsea Boots.

And the brand here to assist in that upgrade is a certified American classic — and one of my favorite boot brands, aside from that. We’re talking today about Red Wing Heritage, a company renowned the world over for its long-lasting, tough-as-nails boots — a company that can be found, of course, within the digital menswear mecca that is Huckberry.

That’s where we’ll start our journey into the world of Red Wing as we consider the Red Wing Heritage Classic Chelsea Boots.

The Red Wing Heritage brand name nearly speaks for itself, with roots making boots for linemen and outdoorsmen in Minnesota and then, across the globe. They still follow many of those same processes today to craft some of the best American-made boots on the market.

Best Red Wing Heritage boots for men.

That’s a true rarity when you consider that even many of the best boot brands for men are using production methods in countries like Mexico (high-quality methods, at that, but nonetheless!). The Red Wing Heritage Classic Chelsea Boots follow closely along those same lines: Remarkable production methods, expert quality and excellent longevity.

Specifically, the Red Wing Heritage Classic Chelsea Boots are made with a recraftable Goodyear welt design that means the boots can be resoled, and the outsole itself is the brand’s TractionTred design.

That design should provide excellent traction on slick city streets this winter, while rich oil-tanned full-grain leather — the same kind Red Wing has been using for decades — only elevates these boots even further. The Red Wing Heritage Classic Chelsea Boots are the perfect hybrid between rugged work boots and slightly more dressy Chelsea boots.

Best Red Wing Heritage boots for men.

These would pair best with your favorite pair of dark blue jeans, a classic henley and one of the best waxed trucker jackets, but the Red Wing Heritage Classic Chelsea Boots could also be styled up with tobacco-colored chinos, an Oxford shirt and one of the best shawl cardigans.

Dress ’em up slightly, dress ’em down for days in the yard or keep ’em classic to head out for a casual evening — the Red Wing Heritage Classic Chelsea Boots deserve to be worn as often as possible this season, whenever you might need them.

The Friday Read: A Red Wing Boots Giveaway, New Mott and Bow Denim & Tom Brady’s New Sunglasses

Men's Classic Moc 6-Inch Boot in Brown Leather 1907 | Red Wing Shoes

An iconic pair of classic Red Wing boots, and just one of the many covetable pairs on offer from the brand this season.

My friends, it’s time you stepped into fall with a pair of Red Wing moc toe boots (available via UNCRATE) — like the rugged leather boots shown above, in fact. I’ve got some even better news, though. You’ve got a chance to win your own pair of archival Red Wing Heritage boots right now. The legendary footwear company is opening the Red Wing vault this fall, releasing a limited vintage footwear offering each month — one pair per month, with some styles dating back to 1963. Simply head to the brand’s Instagram page to find out more. And if, in addition to trying your luck, you’d also like to buy some Red Wing boots right now, you can snag ’em at retailers like UNCRATE in the meantime. Alright, now that we’ve stepped on into the weekend a little bit, who’s ready to get down to business?

There’s plenty to get excited about in the world of men’s style as we get ever closer to fall. To help you prepare for the season ahead, I’ve started writing for Huckberry’s revamped Journal — it’s back and better than ever, and I’m so pleased to be able to cover the best waxed trucker jackets and plenty more along the way. I’ve also kept plenty busy contributing to Maxim.com to start fall — more on that below, too! And before I put on another pot of coffee and start to scheme my next brewery visit (likely to Brooklyn’s Threes Brewing!), I’ve also got to shout that you can (and should!) hit Subscribe to get my newsletter, The Style Guide In Brief, delivered twice-weekly to your inbox — every Tuesday and Saturday, in fact. I’m talking indie rock, craft beer, the best fall gear and much, much more. How about it? Of course, you can also swing back through the blog tomorrow to check out my Style Pick of the Week. The rest of your Friday Read awaits below.

Men's - Faherty Brand

The best way to prep for the season ahead? Gear up with Faherty Brand, folks.

American Giant Hoodie Review - AllOutdoor.com

  • Here we are with more of the best gear for a fall weekend. In fact, it comes from a brand you probably recognize from the blog: That, my friends, would be the good folks at American Giant. With a focus on casual, rugged men’s basics — including the best hooded sweatshirt for fall — the American Giant team is on the case when it comes to outfitting you in easy-going yet cool style for the season ahead. After all, when you put in the hours and focus on American-made menswear, the results are going to speak for themselves. Note that the brand has also shifted production to make some of the best face masks on the market during these trying times, too.
  • As I mentioned above, I’ve certainly stayed plenty busy on the writing front, including a recent feature for Maxim.com that’s definitely a highlight of my writing career. I caught up with NFL legend Tom Brady to talk all about his new eyewear collaboration with Danish brand Christopher Cloos! The partnership features plenty of stylish sunglasses and Blue Light eyeglasses, too. Read more before you snap up a (surprisingly affordable!) pair.

Well, how about it? Are you ready for the weekend — and ready to stock up on the best men’s gear for fall, no less? I certainly know I am. In the spirit of always being ready for what lies ahead, I’m going to point you toward my 25 best men’s gear picks for fall, an extensive offering (if I do say so myself) that really does have something for everyone. To wit: I cover everything from stylish leather boots to American-made socks, classic Persol sunglasses Filson Dry Tin 5-Pocket Pants and much, much more. Sounds too good to pass up, does it not? My friends, thank you for reading, thank you for being here & let’s start the weekend off right.

 

The Friday Read: Raf Simons, Red Wing Heritage and Usain Bolt

Editor’s note: Expect these posts once a week on Fridays — consider this a jumpstart on reading for your weekend downtime. Expect a mix of style and non-style content. For more entries, click here.  

This past week was all about reflection and appreciation for me — appreciation for a great weekend spent in Michigan, appreciation for the chance to head back to my home state again in just two weeks for my good friend Andy’s wedding, and appreciation for what’s so far been a great summer in NYC. I’ve had the chance to take in some excellent concerts by my favorite bands, I’ve had the chance to travel, and I’ve also had the chance to explore the Big Apple with amazing friends — seriously, put an NYC trip on your bucket list. With all that being said, it’s still tough to believe we’re already into August. But, that means one of the best times of the year for us #menswear fans isn’t too far off — we’re talking, of course, about fall, and all the great style transitions it brings with it. Looking too far ahead? Perhaps. For now, I’m looking forward to a relaxing, warm weekend in the city before I get ready to travel across the country in the next half of the month (a family visit to Florida and a work trip to Las Vegas are in order). If you’ve got your own summer travel still left on the horizon this weekend, accessorize with a stylish dopp kit or a functional weekender bag. And in the meantime, kick back and enjoy the Friday Read. To keep up with daily style inspiration from the blog, head over to Instagram.

  • Even if you’re not into fashion (that is, fashion with a capital “F,”) shockwaves went through the industry this week when it was announced that Raf Simons is the new creative director at Calvin Klein. The former creative director at Dior, this is his first foray into American fashion; ultimately, it could signal a new direction for the iconic American brand — and it likely means they’ll be back in a big way at next year’s New York Fashion Week: Men’s, among other fashion week happenings.
  • For those who like their athletic performance mixed in with some eye-catching style, check out FOURLAPS — named for the number of laps it takes to run a full mile, the folks at Valet recommend you look at this new athletic brand that’s mixing up the market.
  • Red Wing Heritage is back with a mighty interesting release, partner — the brand just launched its Pecos Collection, featuring two silhouettes inspired by the boots worn by Western ranchers all the way back in the 1930s. It’s a style that’s probably not for everyone, but if you’ve grown weary of your trusty suede chukka boots or even leather chukkas, you might consider grabbing a pair.
  • Long Read of the Week: It’s been a while since this entry made an appearance in the Friday Read, but its return is a fascinating one. The New Yorker looks into (with varying responses) how fast Usain Bolt would run the mile — yes, read on and ponder away.

What else is on your reading list? Make it one of these pieces, will ya?

  • There’s no better time than August to slip your feet into some stylish boat shoes before Labor Day — check out my list of the 10 best boat shoes for men over at GearMoose.
  • For rock-ready style that’s just as modern today as it was in 1970s, turn to the new Levi’s 505C — I had a blast covering the brand’s latest launch for The Manual, and know that these jeans (as seen on my Instagram) really are way comfortable.

Buck Mason - Timeless Design. Made in America.