Folks, maybe it caught you off-guard, out of the blue. Perhaps you woke up on a recent weekend and realized some breezy, ever-so-slightly crisp fall weather had snuck up on you. Well? What’s a guy to do when it comes to getting dressed for a fall weekend? The gear you wore in the past (college sweats, anyone?) isn’t quite up to snuff now, so I’ve got the answers — fear not. It’s high time you prepped for fall with another unstoppable #OOTD filled with, well, the best fall gear for men, my friends. And if you’ve been wondering how to dress for a fall weekend in style — and in a way that’s different from the casual menswear so many of us are now rocking at home during the week — you’re in luck.
Dressing for a breezy, cool, fall weekend should be fun, versatile and ready for anything, so trade in those old sweats. Whether you decide to dash out to the brewery to snap up some Oktoberfest beers (wear a mask!) or whether you’re heading out of town on a day trip or an orchard visit, these picks will get the job done. We’re talking one of the best casual jackets for fall, worn atop a Todd Snyder + Champion sweatshirt, for starters. Other accessories are along for the ride, including a casual Shinola watch. And if your day is spent in closer proximity to home, pieces like one of the best Bluetooth speakers of the moment are included in this ensemble, too (heck, once you see this speaker, you’ll want to pack it up to bring to your cabin). The point is this: Versatility and casual comfort — yet serious style points — are the M.O. of right now, so be sure you’re stocked up on all the best men’s from head-to-toe (stylish vintage ballcap included). Good luck out there, and feel free to let me know what you think of this look on Twitter.
- The Jacket: Relwen Windzip Jacket, $258 — Perhaps your casual fall weekend actually involves dashing through fall weather to re-stock your beer fridge; whatever the case might be, wear one of the best casual jackets for fall to do so.
- The Sweatshirt: Todd Snyder + Champion Lightweight Pocket Sweatshirt, $98 — Fit for fall layering, Todd Snyder + Champion deliver one of the best crewneck sweatshirts on the market. You’ll reach for it every fall weekend.
- The Classic Henley: Marine Layer Henley, $54 — Look put-together when you want to ditch any of your top layers. This classic henley is a nice base layer for fall, and you can even wear it all on its own underneath the Relwen Windzip Jacket.
- The Laidback Pants: Marine Layer Saturday Pants, $125 — It’s official: These are some of the best casual pants of the moment, and the fact that the Marine Layer Saturday Pants are so aptly named is a huge bonus. These are a blend of five-pocket pants and joggers, making ’em some seriously comfortable men’s pants, folks.
- The Sneakers: GREATS Court High Sneakers, $209 — Searching for some of the best high-top sneakers for men out there? The GREATS Court Sneakers are it.
- The Watch: Shinola Guardian Watch, $670 — Here’s the deal, folks. This is one of the best casual watches for men out there, complete with a refined dial and yet a laidback, rugged NATO strap option. Purchase this Shinola watch ASAP.
- The Socks: American Trench Retro Stripe Socks, $30 (Three-Pack) –What better pairing alongside high-top sneakers than some of the best socks for men, and made by the one-and-only American Trench, to boot?
- The Audio Essential: Master & Dynamic MA770 Wireless Speaker, $1,199 — For plenty of days at home this fall, get one of the best Bluetooth speakers of the moment, an investment-level home speaker from Master & Dynamic that should sound absolutely incredible, no matter where you’re listening to it.
- The Hat: Filson Washed Low-Profile Cap, $45 — You know that tried-and-true, vintage ballcap you’ve had for years? This Filson ballcap is a lot like that. Throw it on before you head out the door to complete this fall #OOTD with one of the coolest men’s hats around.
Whatever your weekend has in store — but especially if it’s got a mix of at-home hangs and adventures in the wild and across town — this #OOTD can handle it. It all starts, fittingly enough, with the Relwen Windzip Jacket, one of the coolest men’s jackets for fall, and one that’s easy to layer and ready for breezy seasonal weather. And how else to complement it for style out & about (or again, at home) than with one of the best crewneck sweatshirts from NYC’s Todd Snyder? It’s a recipe for success when you consider the base layer you’re working with: A rugged men’s henley that works just as well on its own as when layered up.
The reason this look works so stylishly is that it’s a step up from the ordinary — as in, some of the best casual pants are the right way to swap out your typical sweatpants. The whole ensemble looks even better (casual yet still cool) when you lace up the GREATS Court Sneakers, and naturally, the excellent Shinola Guardian Watch is one of the best men’s casual watches you can buy. Elsewhere, a pair of the best socks for men are as necessary an accessory as any, and American Trench is going to ensure that even your socks look darn stylish. As mentioned above, days at home — and even trips to your cabin — call for some essential listening, and the Master & Dynamic MA770 Wireless Speaker is as good as it gets. Top it all off with a rugged ballcap, then start planning out your weekend — you’ve earned it. To see how I’m dressing for fall, follow me on Instagram.