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

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