Style Pick of the Week: Wolverine 1000 Mile Roughout Boots – Coolest Fall Boots for Men

When the calendar rolls through fall, that means one thing — if you ask me, at least, that means it’s time to lace up a pair of the most rugged boots for men. And for this Michigan native, that means you need to turn to Wolverine, a longtime favorite and a legendary boot brand. They now do everything from craft the coolest men’s sneakers to, well, the best men’s boots.

Faherty

There are plenty of different editions of the Wolverine 1000 Mile Boots, including the Wolverine 1000 Mile Moc Toe Boots, but right now, the Wolverine 1000 Mile Roughout Boots are the pair to get in your closet and on your feet ASAP. Crucially, the Wolverine 1000 Mile Roughout Boots are based on the brand’s archival 1914 silhouette, with the modern-day, dependable specs to match (keep scrolling).

Best fall boots for men.

As if that wasn’t classic enough, the Wolverine 1000 Mile Roughout Boots feature the brand’s carefully crafted outsole with both Vibram technology and a leather heel. Speaking of leather: The impossibly cool Wolverine 1000 Mile Roughout Boots use rich, textured roughout leather that’s been waxed to bolster its character and good looks.

If you want a pair of stylish men’s boots designed to get better with age, the Wolverine 1000 Mile Roughout Boots should be your next seasonal go-to.

HELM Boots

Better still is the fact that these boots are handmade in the U.S.A, yet the price is much more than agreeable — the Wolverine 1000 Mile Roughout Boots will run you $385, a downright steal when you consider the fact that you can wear them day in and day out in casually rugged style situations from fall to winter.

For starters, pair them with your favorite flannel shirt and the best men’s blue jeans, then keep your season rolling the right way. When the calendar hits October, yessir, go with the Wolverine 1000 Mile Roughout Boots.

Style Pick of the Week: Todd Snyder Guide Shirt – Fall’s Most Refined Shirt Jacket

Best men's shirt jacket for fall

If ever you were looking to strike the right balance between rugged and refined, there’s no time like fall to really take care of business with the best men’s style essentials. And for my money’s worth — as you know if you scour The Style Guide for the best fall style picks on the daily, few designers do that better than Todd Snyder. The Iowa-born designer takes the classics and upgrades them in ways that make them work in both NYC and back in the Midwest, as with the handsome, well-made Todd Snyder Guide Shirt.

It’s the perfect example of the, well, rugged-meets-refined look championed by the brand, and that makes the Todd Snyder Guide Shirt a unique addition to your fall and winter layering. The key is the soft-yet-dependable blend of virgin wool, acrylic, polyester and other fibers (for comfort and stretch) into one seriously cool, stylish fall shirt meant to be layered up as one of the best men’s shirt jackets. And folks, your new favorite fall shirt jacket only gets better from there.

Most rugged men's shirt jacket

The Todd Snyder Guide Shirt also boasts retro elbow patches for a neat and distinctive touch — this rugged men’s shirt jacket is less refined than one of the best fall blazers, to be sure, but no less ready for unique layering. That means you can style your new favorite shirt jacket atop a rugged men’s henley as readily as you can use it as another layer atop one of the best men’s Oxford shirts.

It’s cut with a more full fit for fall and winter layering, too. Plus, color options like a rich Blue-Brown Plaid or the fall-friendly Mustard Multi-Plaid certainly give you options. Beware that this Todd Snyder shirt clocks in at a pricey $268, but as with other Todd Snyder menswear essentials, I’m betting that higher price tag will pay off in spades.

Style Pick of the Week: Flint and Tinder Waxed Hudson Jacket – Fall’s Coolest New Jacket

Isn’t it a thing of wonder when one of your favorite brands gives you plenty of options when it comes to the best fall jackets for men, for instance? That’s certainly the case with the good folks at Flint and Tinder, the brainchild behind one of the best online menswear shops — that’s Huckberry, of course. The company specializes in rugged, versatile, utterly timeless gear, and for my money’s worth, the Flint and Tinder Waxed Hudson Jacket is just the latest standout style move from the much-loved in-house brand.

Milled in Scotland for a lifetime of wear.

Of course, I’m willing to bet you know Flint and Tinder through its most famous product – – that’d be the Flint and Tinder Flannel-Lined Waxed Trucker Jacket, what with its durable construction and hard-wearing design. Of course, the Flint and Tinder Waxed Hudson Jacket is a star in its own right, with detailing and a build that makes it one of the best men’s jackets for fall (quite handily, at that). In fact, take it from me: I’ve had the chance to review this Huckberry jacket, and can vouch for its quality, style and sturdy durability.

Most rugged fall jacket for men.

This expertly cut, perfectly rugged piece of outerwear has the potential to become your new favorite fall jacket, what with its hunting coat-inspired design and a plethora of touches that make it insanely cool and insanely comfortable. For starters, the Flint and Tinder Waxed Hudson Jacket offers more coverage than the Flint and Tinder Flannel-Lined Waxed Trucker Jacket, which is useful when inclement weather hits.

Flint and Tinder jacket review

This sturdy fall jacket is crafted from British Millerain waxed canvas that’s been treated for additional weather resistance, and the flannel lining of the Flint and Tinder Waxed Hudson Jacket is a brilliant addition to a casually rugged jacket that’s ready for just about anything.

Fully fashioned crewneck sweater to keep you warm against the harshest winter climates.

It even features a rear game pocket, in addition to front hip button pockets and an interior chest pocket, all the better to secure your everyday carry essentials. For good measure, the Flint and Tinder Waxed Hudson Jacket comes in a range of pleasantly fall-like colors, so you can style it with plenty of other Flint and Tinder essentials. When your fall wardrobe requires a rugged change of pace, you know just the brand to shop right now.

Style Pick of the Week: Taylor Stitch Crawford Sweater – Fall’s Most Rugged Cardigan

Best men's cardigan for fall

My friends, it’s like I keep saying: There’s no time like the present to properly layer up for fall, and it’s easier than ever to get prepared thanks to one of the best men’s cardigans to hit the market in some time. You might recognize the Taylor Stitch Crawford Sweater from this very blog, because it’s a personal favorite and just one among many of the best men’s style essentials made by the legendary-yet-modern menswear brand out of San Francisco.

Yes indeed, if I had to guess, I’d say the Taylor Stitch Crawford Sweater is going to become an essential, rugged, highly warm and highly stylish menswear move for the rest of the season, and I’d urge you to act quickly to make it yours. It’s the optimal sweater to join other rugged, classic menswear picks from the brand, including some of the best men’s boots for fall and classic Taylor Stitch shirting, and it just gets better from there.

Most rugged fall cardigan for men.

This classic men’s cardigan is just part of what awaits you within the well-stocked Taylor Stitch New Arrivals section, and it’s not hard to see why the company brought back one of the best men’s sweaters for fall and winter. The Taylor Stitch Crawford Sweater is made from sustainable, 100 hundred percent Better Cotton (part of the Better Cotton Initiative), which means it’s both eco-friendly and easy to layer up over everything from a Taylor Stitch henley to a Taylor Stitch shirt.

Plus, the Taylor Stitch Crawford Sweater features handsome details like horn buttons — which turns this from a house sweater into a rugged-yet-refined cardigan you can wear out and about — plus a rugged, throwback-oriented shawl collar that frames your face.

The Taylor Stitch Crawford Sweater gets all the details, no matter whether you select the Rust or Charcoal colors. Given that you can rock this at the office, on the road or at home, the Taylor Stitch Crawford Sweater (at $168) is a worthy fall and winter menswear investment. Shop accordingly today, my friends.

Style Pick of the Week: Frye Tyler Chelsea Boots – Best Men’s Chelsea Boots for Fall

Best men's Chelsea boots for fall

Among any list of the best fall style essentials — be it one of the best fall blazers or your new go-to henley — you’d also do well to consider some of the most rugged men’s boots, right? But there’s a fine line to walk, literally, if you want to maximize your versatility. While there’s a time and a place for hard-wearing work boots, you can still get fall-minded performance and style with *drumroll please* a pair of the best men’s Chelsea boots. In fact, at the current moment, there might not be a better pair of men’s boots for fall on the market than the FRYE Tyler Chelsea Boots.


You’ve hopefully encountered the brand through its penchant for making some of the best leather boots, period, but the American heritage footwear company continues to step up its game with timeless styles like the easy-on, easy-off Chelsea boot. It all starts, of course, with quality leather when it comes to the FRYE Tyler Chelsea Boots, and in this case, we’re talking a rich Cognac leather that wears well with plenty of fall style picks (everything from dark blue jeans to black denim to olive chinos).

The FRYE Tyler Chelsea Boots — which are selling somewhat fast despite a more investment-minded price tag of $328 at FRYE — also sit atop a sturdy leather outsole for traction on slick fall streets and through day-to-night pursuits (anyone up for a park stroll and brewery visit?). Better still, the FRYE Tyler Chelsea Boots are designed for a smooth ride, thanks to the injection of a rubber forepart in the leather outsole.


The end result is a pair of sleek yet hard-wearing boots, the kind you can team with wool trousers, stretch cotton chinos or your favorite pair of blue jeans without missing a beat. On your top half, go with rugged picks like one of the best men’s henleys or keep things a touch more refined with a cool cotton blazer. Either way, be sure to get as much wear as possible out of the FRYE Tyler Chelsea Boots, because they can take it.

Style Pick of the Week: Filson Lined Tin Cloth Cruiser Jacket – The Rugged Jacket You Need This Fall

As summer draws to a close slowly but surely, it’s time to turn your attention towards the business of getting ready for fall with the most rugged menswear on the market. Of course, you know that if you read The Style Guide.

Beyond that, you know the score if you’ve been keeping up with the goings-on at Filson, you know the legendary Pacific Northwest heritage outfitter can help you gear up for (eventual) cold weather in style. Perhaps you’ve already picked up one of the best crewneck shirts for layering, or else snagged one of the best lightweight shirts for men — but let’s amp things up even further today, shall we?

The Filson Lined Tin Cloth Cruiser Jacket is our featured Style Pick for good reason: It’s a certified classic, built to last and fashioned with ridiculously tough specs, and it’s now back and better than ever in a fall-friendly color.

You’ll find your new favorite fall jacket is as reliable as they come, made from Filson’s legendary Tin Cloth fabric and now lined with durable 6 oz. canvas (and the Filson Lined Tin Cloth Cruiser Jacket is also lined with polyester in the sleeves). Keep on scrolling, because it gets even better.

Best Filson jacket for men this fall.

It really is the Tin Cloth fabric that makes the Filson Lined Tin Cloth Cruiser Jacket such a fan favorite — it’s been around for more than a century, after all. Water-resistant waxed duck canvas stands up to the elements, to long days on the job and in the yard, and to blustery fall breezes when trekking through town to your favorite coffee shop.

Seriously, the Filson Lined Tin Cloth Cruiser Jacket can just about do it all when it comes to casually rugged style and performance.

In fact, you’d also do very well to pair it up with essentials like a classic henley shirt or a Filson flannel shirt when temperatures start to plummet. Of course, you can wear the Filson Lined Tin Cloth Cruiser Jacket — in either the Cinder or Dark Tan colorways — with everything from durable Filson work pants on the job to your favorite pair of blue jeans for classic off-duty style. As I’ve said before, it’s never too early to get geared up for what lies ahead, and the best fall menswear from Filson can help you get there.

Style Pick of the Week: Filson Lightweight Alaska Guide Shirt – The Best Shirt for Men for Early Fall

Best early fall shirt for men.

The theme of the week here on your favorite Brooklyn style blog has been how to dress in style for early fall, and with good reason — soon enough, breezy weather will be upon us, and it always pays off to gear up early with the most rugged menswear on the market. You’re in luck, because legendary heritage outfitter Filson is welcoming a crop of the best new menswear that gets better each and every day, and that’s especially true when it comes to crafting one of the most classic, best shirts for men.

If you’re searching for the sort of men’s style essentials you can shop now — in the depths of August — and then wear come September and October (and beyond!), the Filson Lightweight Alaska Guide Shirt is your best bet, to say the very least. It’s a Filson icon for a reason, and like, say, Filson’s Waffle Thermal Crew, it’s an early fall style pick you won’t want to leave home without.

Crucially, the Filson Lightweight Alaska Guide Shirt helps you bridge the gap between summer and fall, and it all comes down to construction and quality. It’s been described by Filson as an “all-season workhorse,” and a lightweight 5oz. cotton that’s still durable and yet breathable speaks to that claim quite nicely.

The Filson Lightweight Alaska Guide Shirt is also made with pleated shoulders for ease of movement — and layering, when weather starts to turn colder on you. For now, you should keep an eye on the Filson Lightweight Alaska Guide Shirt — a number of classic colors are up for grabs, with vibrant, classic patterns on the way later this fall. It’s never too soon to stock up on the best men’s style essentials, and my friends at Filson have you covered.

Style Pick of the Week: Alex Mill Double Twill Blazer – The Best Summer Blazer for Men

There will come a time this summer when you’re going to have to step up and look sharp, even in the heat — this is where one of the best men’s blazers can save the day, so to speak. But not just any old blazer will do: Try the Alex Mill Mill Blazer on for size and see the kind of versatility and sharp style that one of the best summer blazers for men can deliver when you need it the most, be it at a summer outdoor wedding, a big-time meeting or a rooftop patio date night. You can rest assured you’re getting quality in the mix — plenty of quality, at that — as this is one of the many casual blazers for men up for grabs this very moment at Huckberry right now.

Shop summer blazers at Huckberry right now

Tailored style is yours for the taking

And the specs on the Alex Mill Mill Blazer absolutely pass muster, as one might expect when shopping for menswear essentials at Huckberry. The garment-dyed 100 percent cotton should prove soft, flexible and summer-friendly, while the design details on the Alex Mill Mill Blazer also check all the right boxes this season, from the casual flap patch pockets to the fact that the Alex Mill Mill Blazer features a classic “three-roll-two” design (a three button-front, rolled to look like the jacket only has two buttons).

Pair it up with light wash jeans and stylish leather loafers for a more casual office look, style it with olive chinos for a tonal date night #OOTD, or else team it with dark blue denim and a white Oxford shirt as we move from summer into fall. But starting right now, the Alex Mill Mill Blazer is the one you need in your corner as the warmer months roll on.

Style Pick of the Week: Billy Reid Organic Cotton Baseball Tee – The Best Throwback Summer Style

Best men's shirt for summer.

For all the times you’re going to have to dress up this summer, I’d wager there will be plenty of days where you just want to dress in easygoing, casual style, perhaps wearing one of the best T-shirts for men, right? And that’s where today’s casual-but-premium Style Pick of the Week enters the fray, courtesy of one of the country’s best menswear designers. The Billy Reid Organic Cotton Baseball Tee is not only one of the best men’s T-shirts of the season — something I can’t get enough of these days — it’s also a prime throwback style move that harkens back to, well, summers spent playing baseball, perhaps.

Although it might look simple on the surface, the Billy Reid Organic Cotton Baseball Tee checks all the right boxes if you want perfectly casual style that’s still visually interesting and not sloppy in the slightest. The Billy Reid Organic Cotton Baseball Tee is made in Peru from 100 percent organic cotton, a nice, an again, premium touch that looks great with everything from classic chino shorts to laidback cotton and linen shorts.

When the weather gets breezy, the Billy Reid Organic Cotton Baseball Tee serves as an easygoing layer all on its own without missing a beat. It’s a bit of an investment as far as T-shirts are concerned (it’s $98, after all), but that kind of utility will help that price tag pay off in spades. Time to layer up, my friends.

Style Pick of the Week: Wellen ’66 Stretch Boardshorts – Summer’s Best Boardshorts

Best men's swim trunks for summer.

Back in the day, years ago, boardshorts used to get a bit of a bad rep, did they not? You know the ones I mean: Baggy boardshorts with way too many pockets, the kind you might have worn growing up (no harm, no foul!). But that’s all changed: The best men’s swim trunks for summer, like the Wellen ’66 Stretch Boardshorts, are both better-fitting, more mature and just cooler (seriously!) than the pairs you might have worn back in the day, and that makes them a worthy candidate for today’s Style Pick of the Week.

It all comes down to the fact that the Wellen ’66 Stretch Boardshorts boast a vintage-inspired cut that streamlines things from a pair of early 2000s boardshorts, and that’s a great thing for all involved. The moisture-wicking and quick-drying, lightweight fabric also gives you added mobility in the water and on land, another major benefit of upgrading your boardshorts in a modern manner. Above all else, the Wellen ’66 Stretch Boardshorts add some serious style points to your summer swimwear rotation.

They’re also part of Huckberry’s sustainable in-house brand Wellen, another major benefit if you want to upgrade your style the right way this season. Plus, you get your pick between sun-faded color options aplenty when it comes to the Wellen ’66 Stretch Boardshorts, and they retail for the agreeable price of $68, meaning you can pick up more than one pair with relative ease if you so choose. The next time you get the feeling your boardshorts need a style upgrade, snag the Wellen ’66 Stretch Boardshorts.