Online Shopping Picks: The Best Men’s Boots to Buy This Fall

My friends, it’s that time of the season again — time to talk about the best men’s boots to buy for fall. The season is, as I’ve said in past weeks, perhaps the best for us #menswear fans — particularly if you’re a fan of rugged fall style essentials. We get to break out our favorite layers, from a slim denim trucker jacket to a rugged striped henley, and better yet … we get to break out stylish leather boots aplenty all along the way. A great pair of leather boots can complement nearly any outfit, and I think you’ll find that the picks below do just that. A herringbone blazer and slim dark denim? Throw on a pair of classic leather chukkas. A casual striped henley and grey selvedge denim? Stylish suede boots ought to do the trick. And that’s just the tip of the iceberg when it comes to the below picks.  Again, the right pair of leather boots  — affordably priced, well-made and supremely stylish — can take you from football tailgate to bar crawl and back, with a week of work in between, of course. So, start checking a few items off your men’s style wish list this season; I know I’ve got a few more picks to add to mine. Follow along on Instagram for real-time style updates, and let me know how we’re doing over at The Style Guide Facebook page.

#1. Original Chippewa 6-Inch Service Boot in Crazyhorse — $270
Original Chippewa

A not-too-bulky pair of rugged fall boots featuring durable construction and great looks.

Believe you me, it’s tough to play favorites when it comes to rugged leather boots for the fall season — but Original Chippewa just might take the cake when it comes to the  brand’s 6-Inch Service Boot. With a rugged silhouette that’s not too bulky — plus premium construction and a quality price — the 6-Inch Service Boot is darn near the whole package. Wear it with your favorite pairr of dark denim and a black moto jacket for edgy weekend fall style.

#2.  Hudson Shoes Elmore Boot in Black — $270

A sleeker, modern combat boot with plenty of style to burn.

Fancy something a little more sleek and less rugged? Hudson Shoes has what you’re looking for when it comes to the Elmore Boot. With the look of a classic combat boot, the Elmore Boot should lend itself well to rock n’roll-ready outfits — think slim, faded grey denim and a stylish graphic tee. The slick black color also lends itself to dressier pairings — if you’ve got a tan or grey herringbone suit in your rotation, the Hudson Shoes Elmore Boots are the boots with which to wear it.

#3.  Astorflex Bootflex in Dark Khaki — $190
Astorflex Bootflex

A rugged-yet-comfortable pair of lace-up boots.

Long a favorite around these parts for blending sustainability and great looks, Astorflex has been making — in recent months, anyways — what could just be your new favorite pair of boots — the Astorflex Bootflex in Dark Khaki.  Finished with a natural rubber sole for comfort and done up in a versatile shade of deep tan, the Astorflex Bootflex should work quite stylishly for plenty of casual fall outings — from the pumpkin patch to your next football tailgate.
#4. Red Wing Iron Ranger Boot in Harness — $300

As good as it gets — the legendary Iron Ranger Boot from Red Wing. Bravo, folks!

As legendary a pair of fall boots as it gets, Red Wing absolutely delivers the goods when it comes to its lauded Red Wing Iron Ranger Boot. Blame it on the Americana craze of the mid-aughts, but the Iron Ranger Boot has taken on a life of its own — and with good reason. It’s a ridiculously rugged, stylish and wearable boot that’ll break in beautifully over time. What’s not to love about that? A job well-done to Red Wing on this one.

#5.  Hudson Shoes Leiwston Chukka — $110

A sleek pair of chukka boots, made with versatile style in mind.

We’ll throw some classic leather chukka boots in the mix this time, just for fun (wink, wink). As first seen in our Style Pick of the Week series, the Hudson Shoes Lewiston Chukka blends a truly excellent price with quality craftsmanship and versatile style. These stylish leather chukka boots — this pair is an admittedly popular seller — can team with nearly anything in your wardrobe, from a worsted wool navy suit, a pair of slim grey denim or a faded pair of blue jeans.

Honorable Mention: Astorflex Greenflex Rough in Sand — $150

An updated take on the Astorflex Greenflex — the durable, treaded sole is a key point of differentiation.

As previously seen in this site’s See Now, Buy Now series, the Astorflex Greenflex Rough is a recent addition to the brand’s line of stylish and sustainably made boots (but you know all about those already). And the Greenflex Rough updates the classic suede chukka in a few crucial ways, starting with the durable sole featuring a treaded grip. It’s a neat tweak on a pair of boots that’ll work with broken-in denim, olive chinos or burgundy corduroys this season.

That wraps up our take on the season’s best boots, folks. What did you think? Any particular favorites on this list? Again, the versatility and rugged appeal of a pair of boots like the Astorflex Greenflex Rough can’t be emphasized enough — and a classic pair of tough leather boots like the Red Wing Iron Ranger certainly deserves its place on this list, too. Don’t forget the casual, versatile look of the Astorflex Bootflex, too — that’s one pair that you can put a lot of miles on this fall. And if it’s sleek fall style you prefer, the Hudson Shoes Elmore Boots are the ones to buy. Let me know in the comments below or on Twitter as to your favorite style — see you out there this fall!

-Beau

#OOTD: Here’s The Rugged Henley to Wear This Summer

If there’s one item I reach for more consistently than any other — no matter the season — it’s got to be a rugged men’s henley. Yes indeed, in the high heat of summer (the perfect time for a short-sleeve henley) and the chilling depths of winter (hello, slim long-sleeve henley), it’s simply an easy-to-wear, effective and stylish choice. But you knew that, right? After all, we talked this spring about how to upgrade your henley. There’s no question that it can easily layer under your favorite summer blazer or be worn on its own — crucially. And today’s all-new, hyper-stylish #OOTD here on The Style Guide covers perhaps the best short-sleeve henley to buy now — or at least, consider buying. And if you read the blog frequently — and shop the hallowed halls of Style Guide friend Huckberry — you should know the brand that makes it: The inimitable folks at Flint and Tinder.

As it were, the centerpiece of today’s outfit is the Flint and Tinder Supima AirKnit Henley, done up in comfortable, breathable fabric with a modern fit. The rest of this ensemble has all the trappings of a rugged, tough outfit that someone like, say, noted henley wearer Mr. Daniel Craig might enjoy wearing.  At any rate, I hope you’re excited to check out some slim dark blue denim, classic men’s boots and a few other hard-wearing touches — including a rugged casual watch. If I were you, I’d wear this outfit out to your next brew pub crawl or even a quick day trip out to the country. And it’s even got a couple pieces — like a stylish everyday backpack — that might get you from point A to point B in many a situation. I don’t want to ruin all the fun, though. Read on below and let me know how you like these #menswear picks!

Rugged men's henley

Take your (new) favorite rugged henley and layer it with a crisp bomber jacket, dark denim and tough boots — wear it now sans jacket, and keep this look handy come fall.

The Henley: Flint and Tinder Supima AirKnit Henley, $55 — First things first: Don’t be alarmed by the use of black here! This Flint and Tinder henley is crisp and slimming, and gents like Daniel Craig  make frequent use of black tees on their own.

The Bomber: Taylor Stitch Bomber Jacket in Charcoal, $188 — If you know Taylor Stitch, you know that they excel at tough, rugged and yet wearable pieces — this Taylor Stitch bomber jacket works for cool summer evenings and chillier fall days in equal measure.

The Denim: Abercrombie & Fitch Langdon Slim Coolmax Jeans, $88 — A&F, a favorite of The Style Guide, is back with a revamped denim line featuring revamped fits — the Langdon is slim, classic and wearble in August thanks to Coolmax technology.

The Belt: Sturdy Brothers Everyday Belt in Chestnut, $80 — Lest you think accessories don’t matter … think again. The folks at Sturdy Brothers make a heritage-quality belt that happens to mesh perfectly with this look.

The Boots: Astorflex Bootflex in Dark Khaki, $190 — Quality lace-up boots made with sustainable style in mind for under $200? That’s what you get with the surprisingly lightweight Astorflex Bootflex.

(Not Pictured) The Socks: Teva Benny Gold Socks (Limited Edition), $12 — Space can be limited in our #OOTD series, but socks that offer up a pop of pleasingly bright blue should pair well with the A&F dark blue denim.

The Watch: Lum-Tec Combat B35 Automatic Watch, $799.98 — You might say this rugged Lum-Tec watch is the grandaddy of them all. Beastly looks, excellent styling potential, rugged vibes, a handsome leather strap … the  Lum-Tec Combat B35 belongs on any wish list of the best men’s gear.

The Backpack: Topo Designs Klettersack, $188 — Don’t get me wrong, I love a stylish messenger bag as much as the next guy. But if you want a grab-and-go bag for a day trip or a bar crawl — particularly when paired with a rugged menswear ensemble — the Topo Designs Klettersack could be your best bet.

The Sunscreen: Salt & Stone Sunscreen (SPF 30) , $17.99 — Sunscreen is one of those things that’s likely the last item tossed in any bag — with Salt & Stone‘s crisp design (and important functionality!), you won’t forget it again.

Have you given any thought as to where you might take this outfit? It can go just about anywhere — an upstate day trip, a trip to the farmer’s market and your local park, an afternoon at your favorite watering hole … and I’d wager it’s all because of the rugged versatility of the Flint and Tinder henley shown here. And because it can go anywhere, it’s important you grab a similarly tough bag. For instance: Take the Topo Designs Klettersack and fill it with essentials like the Taylor Stitch Bomber Jacket and much-needed Salt & Stone sunscreen. And the best part is that you can easily complement your Flint and Tinder henley with other rugged basics, from dark denim to the crisp, stylish Astorflex Bootflex. What you’ve got on your wrist is equally important — my favorite part of this ensemble might be the Lum-Tec Combat B35. And if you read this blog, you know that the details make the difference — start with a heritage-quality belt and go from there.

Let me know: What do you think of this rugged #OOTD? Drop a line in the comments!

Thanks so much for reading,

-Beau