Best rugged fall gear for men

Shop The Style Guide

Welcome to The Shop by The Style Guide. Consider this a curated selection of men’s style essentials from your Brooklyn-based blog writer and editor (that’d be me, Beau!), updated semi-regularly. It’s a quicker way to shop classic brands through the site without diving into, well, all of my writing. That being said, many of these men’s gear picks make appearances elsewhere on the site (like right here!). You’ll see a curated, mostly rotating selection of the best menswear essentials across all categories (think the best Oxford shirt, the best sneakers, the coolest leather jacket, and so on) coming from brands you know — and some you don’t.

In the spirit of fall, I’m also telling you about the best whiskey to buy now. It’s all up for the taking, folks. Heck, these could become building blocks of your wardrobe (and your bar cart). Enjoy.

Editor’s note: This page uses affiliate links, from which a small commission might be earned. All opinions are my own. Thanks for supporting brands that support The Style Guide! 

Flint and Tinder Flannel-Lined Waxed Trucker Jacket 

There’s no better way to welcome fall than with a classic waxed trucker jacket for the season ahead. $240

Shop Flint and Tinder 

Todd Snyder + Champion Pocket Sweatshirt 

Heavyweight Pocket Sweatshirt in Light Grey Mix

This essential, rugged pocket sweatshirt is as classic as it gets for fall. Wear it with pride. $98

Shop Todd Snyder + Champion 










Everlane Performance Chinos

Fall adventures call for the best men’s chinos. These are a great place to start. $72

Shop Everlane 

FRYE Bowery Lace-Up Boots

 Every guy needs some of the best boots for fall, right? These rugged leather lace-up boots are a must-have. $378

Shop Frye 


Bulleit Bourbon Whiskey 

In the spirit of fall, what pairs up better with FRYE leather boots and a waxed trucker jacket than the best bourbon on the market? $31.99 via Drizly 

Shop Spirits at Drizly 

Levi’s Western Shirt 

Head to UNCRATE to get the best deal on one of the best denim shirts around. $70

Shop Levi’s via UNCRATE 

Master & Dynamic MH40 Wireless Headphones

Let’s step away from menswear toward gear. These are the best Bluetooth headphones to power plenty of days at home. $249

Shop Master & Dynamic 

Rogue Territory Supply Jacket 

As seen famously in previews for “No Time To Die,” this is one of the coolest jackets for men on the planet. $295

Shop Rogue Territory via UNCRATE 

Mott and Bow Slim Staple Jeans

Skinny - Staple - Medium/Dark Blue

You really can’t go wrong with classic blue jeans from a brand known for making the best men’s denim. $128

Shop Mott and Bow 

Buck Mason Curved Hem Henley 

Buck Mason - Natural Pima Curved Hem Henley

Just in time for fall, you need to snap up one of the best men’s henleys ASAP. $52

Shop Buck Mason 

Bespoke Post Weekender Box

Weekender | Bespoke Post - Box of Awesome

Bespoke Post is one of the best subscription services for men out there, and the affordably priced Weekender Box (featuring, yes, a stylish weekender bag) is the right way to go. $45

Shop Bespoke Post

Taylor Stitch Jack Oxford Shirt

Taylor Stitch The Everyday Oxford Jack Shirt - White | Garmentory

Featuring a tailored fit and classic appeal, Taylor Stitch makes perhaps the best Oxford shirt out there. $98

Shop Taylor Stitch

Timex + Todd Snyder Marlin Leather Watch

Exclusive Timex + Todd Snyder Marlin Watch Navy Dial

Consider this the perfect leather watch to wear with each of the above style staples (or really, any shopping pick on this page). $199

Shop Todd Snyder 


Buck Mason Bruiser Bomber Jacket

Buck Mason - Bruiser Bomber

This is one of the coolest leather jackets around, and you’ll have it for years. $495

Shop Buck Mason 


Ibex Wool Journey Long-Sleeve Crew

Journey Long Sleeve Crew

A new season calls for the most comfortable men’s basics, like this stylish long-sleeve merino T-shirt. Ya dig? $98

Shop Ibex 

Bombas Vintage Stripe Men’s Socks 

Listen up, folks. Rugged leather boots or sneakers call for the best socks for men. These are  a perfect pair to buy now. $12 

Shop Bombas 

MWC Military WatchMWC G10 Military Watch - Black

Every guy needs a reliable, casual everyday watch. This military watch is just the ticket. $79

Shop MWC Watches via Cool Material 

Freemans Sporting Club Western Shirt

Made from classic denim, this stylish Western shirt is a seriously cool everyday shirting upgrade — seriously, give it a try. $250

Shop Freemans Sporting Club

HELM Boots Declan Leather Chukka Boots

There’s never a bad time to buy classic leather chukka boots — especially this Texas-made pair. $295

Shop HELM Boots 

Filson Bridle Leather Belt

Hey, every great pair of boots needs a rugged leather belt. $85

Shop Filson 



Myles Apparel Tour Pants 

The most versatile everyday pants you can buy? Possibly. Cut like five-pocket pants, stylish enough for the office, easy to wear on the road. $118

Shop Myles Apparel 








Topo Designs Mountain Shirt

Searching for the perfect shirt for fall adventures? You’ve just found it. $59

Shop Topo Designs 

Hurley Dri-FIT Worker Pants


Casual, everyday pants with the cut of durable work pants and the styling potential of your favorite denim? That’s what you’re getting here. $70

Shop Hurley 

Patagonia Iron Forge Hemp Chore Coat

It wouldn’t be a new season without a rugged, sustainable chore coat from Patagonia. $149

Shop Patagonia 








Billykirk No. 478 Carryall 

Last but not least, how are you going to carry all your new favorite gear? This stylish everyday bag from Billykirk. Easy as that. $495

Shop Billykirk 

Thanks for reading and shopping The Style Guide! Be sure to follow me on Instagram and Twitter for more content. Feel free to sign up for my twice-weekly newsletter, The Style Guide In Brief, where I cover the best menswear, music & coffee, to go along with the best beer and more.