See Now, Buy Now: These R.M. Williams Chelsea Boots from Huckberry are the Best Winter Dress Boots

Navigating the treacherous terrain that comes with winter weather is a pretty daunting task if you’re not equipped with some of the best men’s boots, but how to best get through these slippery, snowy times in style? It’s simple, yet somewhat complicated: For those times when you need to look your best, be it date night, happy hour or a jam-packed day back at the office, step into some of the best dress boots for men to stay on your feet in style. See? Easy as that. OK, not quite, but the R.M. Williams Comfort Craftsman Boots are an ideal solution to blending comfort and style, plus some winter-friendly traction in spades. For the uninitiated, R.M. Williams have been making incredibly hard-wearing, high-quality footwear in Australia since 1932 — to say they know what they’re doing is an understatement.

Sure, the R.M. Williams Comfort Craftsman Boots aren’t quite a super-thick pair of snow boots or a pair of the best moc toe boots for men, so you might want to save them if the occasion is particularly snowy (or better still, pack them in your favorite everyday carry essential so you can change later). But for demanding winter days where sharp style is of the utmost importance, the R.M. Williams Comfort Craftsman Boots get the job done reliably, and then some.

It’s also a mark of good quality — to say the least — that these rugged-yet-dressy boots are sold by Huckberry, one of the best online retailers for men. The R.M. Williams Comfort Craftsman Boots get the Huckberry seal of approval for plenty of reasons, including what Huckberry calls a “supple and durable” leather upper, not to mention the specially designed non-slip rubber welt sole. The sole itself can also be swapped out after excessive wear, although it’ll likely be sometime before you end up having any issues with the R.M. Williams Comfort Craftsman Boots.

You can also take your pick between two handsome and elegant shades of leather (Dark Tan or Black) — either pair of the R.M. Williams Comfort Craftsman Boots will prove highly versatile whether paired up with a slim pair of blue jeans, the best pair of corduroy pants or even your finest wool suit for winter. These boots are also carefully crafted from just one piece of leather, an added touch that elevates the R.M. Williams Comfort Craftsman Boots into a wearable piece of luxury. Remember: The no-slip rubber sole is really what makes them some of the best winter dress boots for men. When you need to keep moving through city streets with style and utility in mind, step into the R.M. Williams Comfort Craftsman Boots — your feet will thank you.

See Now, Buy Now: The HELM Boots Jakob Boots are the Best Pair of Boots to Lace Up Now

Who among us can pass up the chance to buy some of the best leather boots for men, particularly in the brisk winter months, right? I know I certainly can’t turn down the chance to both shop and buy a fresh new pair of rugged leather boots, especially to end one year and head into the next in style. If you ended up with some extra Christmas cash, for instance, then investing in some of the best new leather boots from Austin-based HELM is never a bad decision.

I’ve long been a fan of HELM’s richly crafted leather boots (check out my HELM boots review for the full scoop), and with the HELM Jakob Boots, it looks like they’ve done it once again.

What exactly does “it” mean when it comes to the HELM Jakob Boots? Well, it’s both simple and yet not quite so simple. It starts, of course, with the work boot silhouette, a tough-as-nails style originally introduced into the HELM line in 2018. Now, the HELM Jakob Boots are back in the mix, with the same silhouette, the very same standout rubber cushion sole and the same handcrafted quality.

The HELM Jakob Boots also really lean into the brand’s penchant for high-quality, rugged and extremely dependable boots. In this instance, that means they use Blake Rapid Welt Stitch construction, which sews the upper of the boot onto a two-part lower half: A midsole sewed onto a rugged outsole. T

his gives it another layer of toughness and durability, ensuring that the HELM Jakob Boots aren’t messing around when it comes to tough performance and seasonal appeal. Make no mistake though, these boots aren’t ultra-heavy or clunky. The lightweight, cushioned yet dependable rubber outsole makes them some of the best boots for men, providing traction and workman-like performance on slippery city streets.

It also helps that the HELM Jakob Boots feature rich, gets-better-with-age Krumenauer leather in Brown (Krumenauer has been around for well over 100 years). Yes indeed, the specs on the HELM Jakob Boots are undeniably cool and built to withstand plenty of wear and tear.

And although these are a work boot style, they’re streamlined enough to be worn with your favorite pair of chinos, plus a rugged denim trucker jacket (to name but one style pairing). They can also be worn readily with broken-in blue denim and your favorite henley, but a classic Oxford shirt is a prime style move, too. Throw on a shawl cardigan and you’re ready for a winter day at the office or beers at your favorite brewery. That’ll work just fine, won’t it? Lace up the HELM Jakob Boots to ring in the new year and the rest of winter in style.

See Now, Buy Now: The Taylor Stitch Wharf Sweater is the Cozy Winter Layer to Shop Now

Although 2021 is winding down, we’re certainly not out of the woods yet as far as needing to dress in cozy winter style is concerned, and that’s where one of the best men’s winter sweaters simply needs to enter your wardrobe right now. And as you might have guessed, you’re not going to be able to go just anywhere to get said winter sweater. Head over to Taylor Stitch and revel in the wonder that is the perfectly rugged, classic and carefully crafted Taylor Stitch Wharf Sweater, one of the best sweaters for men and an outstanding addition to the Taylor Stitch New Arrivals section as of late. Now, you should also shop the jam-packed Taylor Stitch Workshop, but the great news is, this sweater is available for purchase right now. It’s got just about everything you should look for in a sweater to wear once the going gets tough (AKA frigid, blustery and snowy), starting with a rich and eye-catching thick knit that calls to mind old-school sweaters that a certain writer (perhaps Hemingway himself) might have enjoyed wearing.

If that’s not enough to convince you, well, rest easy knowing that the Taylor Stitch Wharf Sweater has plenty going for it beyond just epic throwback looks. It starts with its 100 percent merino wool construction, the sort that provides both extreme warmth and yet moisture-wicking, anti-microbial properties. How can one sweater do all of that at once? Well, it’s the Taylor Stitch Wharf Sweater we’re talking about, after all.

Simply put, the Taylor Stitch Wharf Sweater doesn’t mess around when it comes to providing incredible protection from the elements, plus top-notch layering potential. Style the crewneck design of the Taylor Stitch Wharf Sweater atop an Oxford shirt or a chambray shirt for the office or for a more casual winter soiree. You could even wear it underneath a waxed field jacket for exceptionally rugged, go-anywhere seasonal style in the elements. And it nearly goes without saying, but the Taylor Stitch Wharf Sweater‘s handsome Burgundy colorway is the stuff winter style dreams are made of. That color in particular pairs well with indigo denim or tan corduroy pants in equal measure, so make sure your menswear rotation is well-stocked.

And the Taylor Stitch Wharf Sweater is, crucially, available for purchase right now, so rejoice in the fact that you can get it delivered to your door with free shipping and free returns. Like other Taylor Stitch pieces worth buying, the Taylor Stitch Wharf Sweater doesn’t exactly come cheap (it retails for $238 at Taylor Stitch), but this is a bold and near-perfect winter sweater to buy now and wear as often as you can this season. Act accordingly, my friends. And thanks for reading!

See Now, Buy Now: Filson’s Watch Cap Beanie Is the Best Winter Hat to Shop Now

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When the weather turns especially treacherous this winter season, there’s one brand that’s going to come through in the clutch above all others, and that’s Filson. The Pacific Northwest heritage outfitter has long excelled at outfitting plenty of outdoorsman for rugged pursuits aplenty, and that includes stylish guys like yourself, even if you’re more inclined to dress for the city than the country. Enter the Filson Watch Cap Beanie, one of the best winter hats for men and an unstoppably warm yet surprisingly stylish and utterly classic men’s winter hat meant for just about anything. It’s got plenty of quality design and a reputation that precedes itself, plus it’s priced under $50 — for an investment-level winter hat you’ll have for years, that’s not a bad thing at all. It also doesn’t hurt that the this essential, no-nonsense winter hat falls right in line with the rest of the brand’s famously well-made style picks, like the best winter coat to the best thermal henley for men. It also helps that the Filson Watch Cap Beanie is a prime way to top off a winter ensemble that’s already heavy on Filson gear to fight off the cold.

The Filson Watch Cap Beanie checks off all the right boxes at every turn, from the use of USA-sourced wool to the thick knit and the agreeable price (again, the Filson Watch Cap Beanie is priced at under $50, a downright steal if you pick up the versatile Olive option that you can wear most every single day).

The Filson Watch Cap Beanie is a bestseller for the brand for a reason, chiefly because it protects so astutely against the cold, from blizzards to blustery days and beyond. You can extend or reduce the coverage on your noggin thanks to the adjustable cuff, akin to the old-school fisherman beanie caps that served seafaring explorers so well. You can also snag the Filson Watch Cap Beanie in a more vibrant Flame color if you’d like to wear it for pursuits in the field, like hunting or fishing. But back in town, the Filson Watch Cap Beanie also looks pretty neat when you wear it to top off a waxed trucker jacket and your favorite pair of blue jeans. When you find a winter accessory that’s both rugged and casual, I recommend you lean into picking it up as soon as possible (remember, the Filson Watch Cap Beanie retails for under $50!). That sure sounds like one of the best men’s winter hats, does it not?

It’s the type of hat made to last through both everyday wear and adventures in the field, as you’ve come to expect from Filson. And the fact that it’s both affordable and yet high-quality should provide a serious upgrade from other winter hats in your rotation. In fact, if I had to guess, I’d say the Filson Watch Cap Beanie is going to be the last winter hat you buy for a long time. If you end up trying it out, let me know in the comments below. Cheers and stay warm out there!

See Now, Buy Now: Get Yourself a Pair of the Best Men’s Shoes from Everlane Right Now

If you’ve trained yourself in the art of savvy shopping over the years, perhaps you know the sustainable menswear being made by West Coast-based Everlane. The men’s and women’s brand has built a substantial following over the years by making menswear that’s accessible, fairly priced and transparently made, including cold-weather staples like the best sherpa trucker jacket, the best lightweight chore shirt and much, much more. Over the past couple years, Everlane men’s sneakers have also become a hot seller, praised for their use of sustainable materials and classic designs. Now though, the brand is taking things a step further with two new additions to its rotation of men’s footwear, both of which are sure to please even the most discerning shopper. Those new additions? Feast your eyes on the Everlane Men’s Desert Boots and the equally cool, equally well-made Everlane Men’s Desert Shoes, all the better for plenty of winter style scenarios (and more) to come.

If you’ve been seeking some of the best men’s shoes, available at agreeable prices and made with classic design in mind, then you’ll love both options, and perhaps the Everlane Men’s Desert Boots especially. Both varieties are made from 100 percent suede, ideal for temperate climates and warm-weather getaways (and even the office, when worn with tailored jeans or chinos). Whether you select the desert boot variety or the crisp, casual-yet-polished Everlane Men’s Desert Shoes, you can’t go wrong.

Both the Everlane Men’s Desert Shoes and the Everlane Men’s Desert Boots are priced to sell at $125, a nice touch that makes either pair equally likely to end up in your shopping cart. And because this is Everlane we’re talking about, both sets of Everlane men’s shoes are made with eco-conscious design in mind, right down to the 94.2 percent virgin-plastic-free sneaker sole. Sustainability counts as much as style these days, and Everlane knows it. The Everlane Men’s Desert Boots also toe the line quite nicely in terms of hybrid style, fusing a desert boot upper with that sneaker sole — this makes them ideal for work, play or travel.

Either option is an expert wardrobe addition, but the Everlane Men’s Desert Shoes are particularly cool and classic, with a design that calls to mind classic Clarks Wallabee Shoes. This makes them a solid style move with, say, slim Everlane blue jeans, tailored chinos or even nicely tapered jogger pants, believe it or not. The Everlane Men’s Desert Boots might be my personal favorite between the toe styles, what with an ankle boot design that gives them maximum versatility and traction on city streets. Both styles are also available in the same two, wear-with-anything colors: Toasted Almond Suede and Pebble Suede. You’ll have to invest in suede protector to get the most out of both the Everlane Men’s Desert Shoes and the Everlane Men’s Desert Boots, but it’s a small price to pay for some comfortable, streamlined and sustainably made shoes.

See Now, Buy Now: Get One of the Best Men’s Henleys for Under $60 at Tecovas

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Isn’t it nice to know that you can go to one place to get plenty of the best men’s style essentials, beyond just, say, the best men’s boots? That’s the case with Tecovas, the Texas-based bootmaker that crafts rugged Western boots and of course, one of the best men’s henleys. It really is like getting a two-for-one deal, knowing that you can step right up and buy rugged men’s leather boots at the very same time that you buy one of your new favorite henleys. What do boots have to do with henleys? Plenty, after all. Boots, especially made in the classic Western and ranch styles by Tecovas, are all about function, purpose and rugged appeal. And the best henleys for men started out the same way, first worn by sporting men in Britain and eventually, utilized as an undershirt. History lesson aside (or perhaps, history lesson included, the Tecovas Waffle Henley is a surefire best bet to shop the next time you pick up some Tecovas men’s boots.

It’s also worth noting that Tecovas — based in Austin — also offers a full range of men’s Western wear and apparel beyond just what we’ve already talked about. They’re a true lifestyle brand if you love Western fashion, if you need hard-wearing gear to get you from point A to point B, or if you just value the ideal blend of old-school craftsmanship and timeless style that you get with everything from the brand’s rugged Western boots to the essential Tecovas Waffle Henley. Why should you consider adding this henley to your cart the next time you pick up a pair of finely crafted Tecovas men’s boots? Allow me to lead the way.

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It really does make perfect sense that the Tecovas Waffle Henley is as high-quality and functional as it is (not to mention, it gives you plenty of bang for your buck at under $60). Yes indeed, Tecovas doesn’t cut any corners with its handsome and ready-for-anything leather boots, which you can wear for work or play. The same can absolutely be said about the Tecovas Waffle Henley, made from 100 percent pima cotton in a waffle knit that makes it an excellent, insulating base layer underneath one of the best denim shirts or your favorite waxed trucker jacket. So, it’s both a lightweight base layer and a henley you can wear on its own, thanks to the unique four-button placket and the textured cotton knit. And of course, it helps that the Tecovas Waffle Henley features elastic sleeve cuffs to customize your fit and layering (go ahead, roll up the sleeves of your flannel shirt).

As if that wasn’t enough, the Tecovas Waffle Henley takes the cake as one of the best henleys for men thanks to its versatility. Whether you pick up the natural Bone shade or the surprisingly rich Washed Navy, this is a henley that goes beyond just an undershirt or base layer. Wear it out in the wild West, wear it on the trail or wear it with some of the best weekend pants for men. It’s ready for anything, just like the brand’s boots. If you end up snagging the Tecovas Waffle Henley, let me know in the comments. Happy layering, folks!

See Now, Buy Now: Gift this Shinola Leather Wallet to the Stylish Man In Your Life (Or Yourself)

If you’ve got a stylish guy on your Christmas list this year (or if you’re building out your own style wish list), it’s hard to go wrong with something as covetable and, well, stylish as one of the best men’s leather watches. That goes for just about anything you’re apt to find at Detroit-based Shinola, which just so happens to be stocking plenty of the best leather gifts for men this season. It’s an impressive assortment, and one that includes the Shinola Pocket Bifold, a handsome and refined leather wallet made for the modern man. And if the gentleman on your list happens to be in need of a new leather wallet, well, that’s really all the better. Yes indeed, the time is right now to upgrade his everyday carry and perhaps, to add a few covetable items from Shinola to your own list. After all, Shinola does so much more than just craft some of the best watches for men. They also happen to make one of the best men’s weekender bags and a throwback-inspired dress watch that any guy would be very happy to find under tree this season. But back to the Shinola Pocket Bifold — it’s an easy choice as far as a seriously upgraded leather wallet is concerned.

The Shinola Pocket Bifold isn’t any old wallet you might find made from cheap materials — far from it, in fact. It’s worth every bit of its $250 price tag, a true marker of quality and not just of a brand name. And the specs on the Shinola Pocket Bifold? I’m glad you asked, friends. It’s made from smooth, rich Vachetta leather, the kind that gets better with age the more you use it (and trust me, he’ll want to use the Shinola Pocket Bifold every single day). It’s neither too bulky nor too flimsy, made with six lined card pockets and an unlined bill pocket, plus a handy receipt pocket. It’s small touches like those that set the Shinola Pocket Bifold apart from others you can buy this season, make no mistake about that.

And it’s all the better to pick up one of the best wallets for men if the stylish guy in your life is already familiar with the esteemed maker of some of the best watches for men. It’s also stamped with the Shinola logo and sewn in the U.S.A. — again, the Shinola Pocket Bifold lives up to the brand’s reputation in every way you’d expect. If the guy in your life expects the best (which I’m sure he does), then the Shinola Pocket Bifold is one way to deliver that, right down to his accessories. Happy holidays, folks!

See Now, Buy Now: This American Giant Waffle Crew is the Coziest Layer to Wear This Winter (And Beyond)

Casual essentials that aren’t so casual — and are actually, surprisingly stylish and well-made — are the name of the game this season, and that’s where American Giant comes into play. If you’ve been looking for upgrades to your laidback looks for cold-weather days and holiday-minded lounging, American Giant can help, and the American Giant Waffle Crew is one of the best men’s shirts to fit the bill quite perfectly. The brand has stepped up its game in recent months, expanding beyond its essential basics to now craft one of the best Oxford shirts for men, and they also do quite the job at crafting plenty of the very best American-made menswear beyond that, too. And if you want a long-sleeve shirt that’s much more than an average long-sleeve shirt, well, the American Giant Waffle Crew delivers on all fronts.

It’s made in Los Angeles, a burgeoning spot for some of the best men’s knitwear, plus denim and the best men’s long-sleeve shirts, to boot. The waffle cotton construction makes this both a distinctive base layer (underneath a rugged shawl cardigan, for example) or a shirt you can wear all on its own with some American Giant men’s pants or tailored joggers. It would also be a valuable piece layered under the American Giant Moto Zip Jacket, for starters. What’s not to love about that? There’s plenty more where that came from, too.

The color and texture of the American Giant Waffle Crew really sets itself apart, too. It’s got an ever-so-slightly lived-in look and feel that’ll only get better over time the more you wear it. And given the 100 percent cotton construction and comfort of the American Giant Waffle Crew, you’ll want to wear this shirt a heck of a lot. Use it as a base layer beneath your favorite waxed trucker jacket, or give yourself some added warmth by wearing it underneath a classic crewneck sweatshirt. You can also style it beneath a rugged flannel shirt for just the right amount of layering on a crisp winter morning. Just about any way you choose to style it, the American Giant Waffle Crew looks great and delivers functional comfort all the way through.

Color options like Evening Blue (shown here) and the deep, dusty red El Camino, deliver just the right amount of seasonal style, making either option practically perfect to pair with faded jeans, grey joggers or even tan chinos beneath an unstructured, garment-dyed navy blazer. It’s rare to find a long-sleeve shirt that can do all of that, but the American Giant Waffle Crew is that shirt, without a doubt. Try it on for size and see for yourself.

See Now, Buy Now: This Waxed Work Jacket from Flint and Tinder Is a Seasonal Wardrobe Essential

When the going gets tough, the tough get one of the best waxed jackets from Huckberry. OK, maybe there’s more to it than that, but ensuring you’re outfitted properly through the worst weather is but one crucial step on the path towards tackling your to-do list (or even a few fun fall and winter adventures). When you’re in need of an outerwear upgrade, there’s one place you can go, and that’s Huckberry — at least, this writer thinks they’re one of the best places to buy one of the best men’s jackets, and that’s just a simple fact these days. And the Flint and Tinder Waxed Mill Jacket is one of the hardest-working, hardest-wearing options on the market at this point. You’re in luck if you’ve been searching for a rugged piece of outerwear fit for work or play, to say the least.

The Flint and Tinder Waxed Mill Jacket has been in the Huckberry rotation for some time now, and offers a change of pace compared to the slightly shorter, trimmer cut of the legendary and much-loved Flint and Tinder Waxed Trucker Jacket. If you’re feeling like one of the best waxed jackets is precisely what you need, consider picking up both. In the meantime though, if you need a workwear-inspired jacket that pulls out all the stops (and does more than just look great), then the Flint and Tinder Waxed Mill Jacket takes the cake (and earns its rightful spot in your wardrobe).

The Flint and Tinder Waxed Mill Jacket is a reliable outerwear pick-up, without a doubt, from the way it’s built right down to the small details (like custom F and T hardware, of course). The waxed and weather-resistant canvas of the Flint and Tinder Waxed Mill Jacket should prove beefy but pliable, and relatively comfortable out of the box. Of course, it’s also going to break in over time and become even more flexible and yet still hard-wearing in its fight against the elements. This is the kind of jacket built for chilly, windy mornings tackling yard work or perhaps just taking down another cup of coffee on a blustery back. Whatever your intended use for the durable Flint and Tinder Waxed Mill Jacket, it can stand and deliver.

Unlike the flannel-lined Flint and Tinder Waxed Trucker Jacket, the Mill Jacket boasts a more substantial, slightly warmer quilted interior lining, with a slightly roomier cut for layering with, say, a thermal henley and a flannel shirt. The lined soft cotton corduroy collar is a standout detail normally found on traditional British waxed jackets, so flip it up to protect against the chill. Store your phone or other EDC essentials in the interior media pocket or the exterior chest zip pocket, and keep warmer with welt hand warmer pockets. The Flint and Tinder Waxed Mill Jacket is built about as tough as it gets, and it’s going to perform like it, as it should for the price (an agreeable $240 at Huckberry). Your new favorite jacket for work — and perhaps a cold beer at the end of the day — is the Flint and Tinder Waxed Mill Jacket.

See Now, Buy Now: This Satchel & Paige Waxed Briefcase Is a New Everyday Carry Must-Have

As we all return slowly but surely to the road, be it through a fall road trip, a stint back in the office or simply a day spent out and about around town, perhaps you’ve realized your everyday carry essentials have been lacking. Particularly when it comes to staying organized in style, it can be a tall order to return to your daily routine without the right gear, and that’s where the remarkable Satchel & Paige Aviator Brief comes into play. It’s a serious upgrade to whatever bag you might be using now (unless of course, that bag is made by the heirloom leather goods purveyors at Satchel & Paige), and it’s one of the best everyday carry essentials for hauling those must-have items to the office or to a day working remotely at your favorite coffee shop (your call these days, folks). Like all bags and leather goods from the Dallas-based brand, its design is rooted in history and its modern look is rooted in functionality, form and some of the best materials you’ve seen put into a lineup of EDC goods.

It’s built with the same approach that Satchel & Paige takes with its full lineup of gear, which was first inspired by a map case used by the founder’s grandfather in World War II. Here, the Satchel & Paige Aviator Brief is also inspired by military bags and is made in Italy from remarkable materials (more on those in a second).

The Satchel & Paige Aviator Brief simply looks incredible and will only get better over time, thanks to the green 20oz. waxed waterproof canvas, which should prove burly and substantial while aging nicely (and keeping your everyday carry essentials safe, of course). It’s lined in handsome Tobacco suede and finished off on the outside with copper rivets for maximum durability at key stress points. Naturally, the exceptional Satchel & Paige Aviator Brief is certainly built to last. Vegetable-tanned French Cowhide leather should also prove thick and durable yet supple, yet retaining a slim profile that’s key to your commute, your road trip or your next flight as a carry-on.

The Satchel & Paige Aviator Brief doesn’t cut any corners, and that’s reflected in the fact that the laptop pocket in the center is strategically placed to avoid scratching your laptop. How’s that for thoughtful, well-executed design? Two exterior pockets also provide easy access to EDC goods, and the included shoulder strap makes it even easier to haul the Satchel & Paige Aviator Brief around town or across the country. What’s more, it’s polished enough to take to the office as you dress in business casual style, but it’ll look right at home with more rugged ensembles, like a flannel shirt layered over a henley with your favorite pair of jeans. Try doing that with a regular leather briefcase, ehh? Point being, the Satchel & Paige Aviator Brief is unlike anything in your everyday carry rotation, so level up and invest in the best now.