Folks, if you’re just now joining us on your search for the best fall style essentials, well, you’re in luck. Today’s post is positively packed with ’em, most of the rugged fall layering variety, including the Faherty Brand Legend Sweater Shirt you see above.
After all, it’s high time you geared up for fall in the right way, and that includes everything from your new favorite boots to an epic shearling jacket from the good folks at MR. PORTER, plus your new favorite jeans. Many of these picks are of the “investment” variety in terms of quality (and price!), but they’ll pay off — trust me. It’s all yours for the taking below, so be sure to let me know on Twitter what picks you end up going with.
Faherty Brand Legend Sweater Shirt — $178
This unstoppable shirt jacket is one of the coolest layers for fall I’ve seen in some time — cool in matters of style, but warm in terms of functionality. Wear it atop a rugged henley for a casual fall weekend.
MR. PORTER Shearling Houndstooth Bomber Jacket — $595
Yes indeed and as promised, here’s your new favorite fall jacket from MR. PORTER. Make no mistake, this shearling bomber jacket is absolutely an investment, but it’s one that’s going to pay off in spades through chilly temperatures this fall.
Everlane Slim Fit Stretch Organic Jeans — $72
For fall and well beyond, every guy needs a pair of slim blue denim with a classic look and feel. These Everlane Organic Jeans are just what the doctor ordered.
Flint and Tinder Black Denim Trucker Jacket — $198
Want to go rugged and edgy with double denim alongside your Everlane Organic Jeans? Then you need this black denim jacket from Flint and Tinder, my friends.
Ollech & Wajs Pilot Watch — $1,245
Let’s go from your new favorite jeans to assuredly your new favorite watch. It’s an investment-level watch with the goods to back it up. The Ollech & Wajs Pilot Watch is modeled after a cockpit control panel, with all the bells and whistles you need to keep track of the time on your fall adventures.
FRYE Bowery Lace-Up Boots — $358
It’s really hard to go wrong with FRYE, makers of some of the best men’s boots on the planet. The FRYE Bowery Lace-Up Boots in particular are incredibly well-made.
Filson Tin Cloth Cruiser Jacket — $350
Alright, ladies and gentlemen. To really tie things together, I’d say you should wear this classic Filson jacket (seriously, the Filson Tin Cloth Cruiser Jacket is the stuff of legend) iwth your FRYE Bowery Lace-Up Boots, your favorite henley and a pair of Everlane Organic Jeans. How’s that for fall style, ehh??
American Giant Roughneck Pants — $144
Let’s keep it rolling when it comes to rugged American menswear, alright? These durable canvas work pants actually have more in common with your favorite chinos than regular work pants, making them durable enough to wear in the field and stylish enough to wear back in town. American Giant does it again, folks.
Buck Mason Heathered Twill Vintage Terry Crew — $75
We’re going to keep it rolling with another one of the best American menswear brands. This Buck Mason crewneck sweatshirt is expertly crafted and perfectly casual — it’s ideal to wear with, yes, your American Giant Roughneck Pants for a fall weekend getaway.
Todd Snyder Italian Mustard Plaid Flannel Buttondown Shirt — $178
Let’s amp things up just a bit with this perfectly crafted, stylish flannel shirt from NYC’s Todd Snyder. This is the kind of classic flannel shirt you can wear on cabin weekends or with crisply pressed slim chinos (because hey, you’re going to have to get dressed again someday).
MWC Classic Retro Military Watch — $79 via Cool Material
Looking for one of the coolest affordable watches out there? Maybe a military watch that blends serious style with rugged functionality? The MWC Classic Retro Military Watch is the one to buy from Cool Material.
United By Blue Organic Canvas Work Pants — $98
When you want rugged work pants for a cold fall morning, a day hike or a country or coastal vacation, you want these United By Blue work pants. They’re sustainable, stylish, rugged and pleasingly cool to wear with darn near anything in your fall wardrobe.
HELM Boots Hollis Boots in Teak — $350
It wouldn’t be a roundup of the best men’s gear for fall without me recommending some of the best boots for men, right? As you well know if you read the blog, HELM Boots (out of Austin, Texas) produce some of the most rugged men’s boots around.
American Trench Merino Activity Socks with Silver — $19.50
Seeing as you’ve now got your eyes on some HELM Boots, you’re going to need some of the best boot socks for men, are you not? I might be biased, but I think American Trench makes some of the best men’s socks, period, including the Merino Activity Socks.

A fun polo to wear on the course or at home this fall.
Ready or not, it’s time to close out today’s edition of The List. I don’t know about you, but I can’t get enough of some of these picks, many of which are quite simply among the best jackets for fall. It’s hard to pick a favorite, whether you fancy a fun golf polo from William Murray Golf or, say, the MR. PORTER Shearling Bomber Jacket covered at the top of the page.
You also shouldn’t sleep on the Veldskoen Heritage Suede Chukka Boots for casual heritage style this season, and I’m a huge proponent of outfitting yourself with the right accessories, including the best boot socks for men from American Trench. On the investment front, of course, I also love the rugged style of the FRYE Bowery Lace-Up Boots, not to mention the expert craftsmanship behind the Ollech & Wajs Pilot Watch. Whatever one of these picks might be your favorite, feel free to talk shop with me on Twitter. Thanks, as always, for reading!