Ready, set … go. I’m talking, of course, about the race to find the best gear for fall to buy for 2022, including some of the best fall boots for men as showcased above. It’s a race we’re running full-speed today, seeing as September is waning quickly and October is just about here. Warmer weather can sometimes stick around into October, especially in NYC, but I’m doing everything I can to break out my favorite fall style essentials, and you should do the same. Whether that’s the Rhodes Footwear Huxley Boots (more on those very soon), a stylish Timex watch, a pair of classic blue jeans or dark blue jeans, you’re going to be mighty pleased with today’s edition of The List. Happy fall, my friends.
Rhodes Footwear Huxley Boots — $220
Rugged-yet-versatile Chelsea boots for all your fall adventures.
Yes indeed, it’s high time we continued talking about Rhodes Footwear and the best men’s boots for fall. These are some of the best slip-on boots out there, with rugged construction and yet sharp styling potential — and it’s all thanks to Huckberry. Think of them like alternative boots to Blundstones, if you will.
Mott and Bow Slim Oliver Jeans — $118
Slim, sturdy dark denim to wear every single day this fall — right?
You know what works extraordinarily well any day this fall (and beyond)? Especially with your new favorite boots? That’s right: A pair of slim dark blue denim from the good folks at Mott and Bow.
Timex Navi XL Red Bezel Automatic Watch — $259 via UNCRATE
Your new favorite watch, quite possibly.
Now, this isn’t the first time we’re talking about this rugged Timex watch on the blog. It’s one of the coolest-looking and most affordable watches out there, and it’ll look great alongside dark blue denim and some of the best slip-on boots.
Schott NYC Perfecto Motorcycle Jacket — $900 via UNCRATE
A stunning leather jacket to wear all the time this fall.
Looking for one of the best leather jackets … ever made? Then it’s the Schott NYC Perfecto Motorcycle Jacket you need, specifically this fine edition as sold by UNCRATE. It’s one of the best moto jackets for fall layering, complete with a cotton flannel lining.
Todd Snyder Lightweight Pocket Sweatshirt in Navy — $98
Your new favorite sweatshirt for fall and winter, guaranteed.
The perfect sweatshirt to layer beneath your Schott moto jacket? Quite possibly. Two NYC brands in one look would make for mighty fine fall style, and this Todd Snyder + Champion sweatshirt is simply one of the best sweatshirts for men this season.
Beckett Simonon Nolan Brogue Boots — $229
Sleek, well-made wingtip boots for fall weather, my friends.
Yes, more of the best boots for fall, folks. These classic wingtip boots are in fact some of the most affordable made-to-order boots out there, so act quickly before fall weather hits.
Buck Mason Chambray Work Shirt in Medium Wash — $105
A tough chambray work shirt to layer or wear all on its own.
What’s a better layer for fall than a rugged chambray shirt, especially this durable work shirt from Buck Mason? Made from 100 percent cotton, you should layer this atop a classic henley (more on that in a minute).
American Trench Retro Stripe Socks (Three-Pack) — $30
Get a three-pack of the best men’s socks to head on into fall, and know that American Trench doesn’t cut any corners when it comes to the best socks for men. These retro-inspired socks are comfortable, easy to wear and stylish as heck when peeking out from your rugged leather boots.
Free Fly Flex Henley — $65
Speaking of the henley you need right now, well, here’s this fine number from Huckberry and Free Fly. Wear this versatile henley any time at all this fall, but especially with that durable work shirt from Buck Mason.
Snake River Farms American Wagyu Ribeye — $179
Bear with me here a second, folks. When you gear up for fall, you should still consider the fact that you’ve got a bit of prime grilling season left. Head to the Huckberry Provisions Shop to get the latest from Snake River Farms.
Myles Apparel Farallon Fleece Jacket — $138
The best men’s casual jacket of the moment.
Get one of the best shirt jackets for fall while it’s still around, then rest easy knowing the Myles Apparel Farallon Jacket is made from cozy, lightweight thermal fleece in a tailored, not overly bulky, fit. And, you can use the code MYLES10 to get 10 percent off right now.
FRYE Mayfield Lace-Up Leather and Canvas Boots — $189
Rugged, tough-as-nails boots from a heritage bootmaker.
Get quite the deal (more than 40 percent off) on these rugged leather boots, delivered to you courtesy of FRYE. Yes, that’s right — we just keep on talking about the best men’s boots for fall, and this pair (complete with waxed-canvas side detailing and Goodyear welt construction) definitely qualifies.
Marine Layer Saturday Pants — $125
Let’s shift our attention ever so slightly towards weekend-ready comfort. These stylish five-pocket pants are built more like joggers for many a fall weekend relaxing or on the run to your favorite brewery, but that doesn’t mean they won’t work with FRYE leather boots.
Tanner Goods Utility Bifold — $100 via Cool Material
Searching for a slim leather wallet that’ll fit stylishly in the pocket of your, say, slim five-pocket pants? Meet the rugged-yet-sharp Tanner Goods Utility Bifold as sold by Cool Material.
Topo Designs 3-Day Global Briefcase — $159
A durable, tough bag that was made specifically for long weekends.
Speaking of everyday carry essentials, why not load up for a quick fall getaway with the Topo Designs Global Briefcase, ehh? Consider it one of the best bags for a long weekend.
Filson Safari Cloth Long-Sleeve Shirt — $125
A durable shirt made specifically for layering from Filson.
You know the rugged men’s gear being produced by Filson can withstand darn near anything, right? This Filson Safari Cloth Shirt is no different, and it’s made to be layered atop your favorite henley or beneath a rugged waxed jacket. How about it?
Everlane Washed Black Denim Jacket — $98
A classic faded black denim jacket in an agreeable fit — well-done, Everlane.
Cruise on over to Everlane to get one of the coolest denim jackets of the moment. The Washed Black color and tailored fit make this classic denim jacket perfect for transitional fall style, especially with a rugged Filson shirt.
Luminox F-117 Nighthawk Watch — $790
A rugged men’s watch made to stand up to anything and everything this fall.
There’s never a bad time to invest in one of the best men’s pilot watches, and with military-grade quality and plenty of experience, Luminox has come through with one of the best men’s watches for fall adventures … and darn near anything else, for that matter.
Billykirk No. 479 Carryall in Black — $550
You’ve got the best watch for fall, plus the best bag for long weekend trips … but what about a durable carryall bag for slightly longer fall getaways? Enter the Billykirk No. 479 Carryall.
Ibex Hero Jogger Pants in Grey — $150
Cozy, sweat-resistant merino wool sweatpants from a standout brand.
This isn’t the first time you’ve seen these stylish jogger pants from Ibex on the blog, and it won’t be the last. Every guy needs comfortable sweatpants for chilly days — these are it.
Are you still with me, folks? Thanks for sticking around to read about 20 of the best fall style essentials for men, starting with some of the best slip-on boots and carrying right on through to other must- have picks, from stylish jogger pants to a rugged Timex watch. I have plenty of favorites from the above list, so it’s tough to narrow it down to my favorite, but I personally love the classic denim jacket from Everlane shown above, along with … those Beckett Simonon wingtip boots. Seriously, I can’t pick just one! To share your own favorites with me this week, be sure to give me a follow on Twitter. Cheers!
The Style Guide 