Just as quickly as we were recommending how to wear your favorite summer T-shirt, we’re now recommending the men’s style essentials to get you ready for early fall. Today’s #OOTD takes a decidedly casual turn, focused on versatile pieces that can tackle fall weekend travel, an outdoor farmer’s market, a beer festival … you name it, I’m sure the below menswear essentials are going to work for you in some way, shape or form. From a classic grey crewneck sweatshirt to an equally classic men’s denim shirt, the building blocks shown here are perfect if you want to up your game ever so slightly without veering too far into formal territory. And if you’re just looking for something relatively easy to throw on the morning after a few too many IPAs, fear not — we’ve got you covered with stretch blue denim and rugged leather boots from Red Wing Heritage. Throw on a stylish field watch (and more choice accessories as seen below), and I’d say you’re pretty much set for early fall. Whaddya say now? Ready to welcome the new season? Let’s step into it in style — cheers.

Rugged-yet-classic shirting, a grey crewneck sweater and more #menswear favorites for your early fall pursuits.
- The Shirt: Taylor Stitch Jack Shirt in Sun Bleached Denim, $98 — There’s something about a classic denim shirt like the Taylor Stitch Jack Shirt that allows it to work season after season — that’s certainly the case here.
- The Sweatshirt: Myles Apparel Elements Crew, $78 — Made with performance fabric, the Myles Apparel Elements Crew manages to nail the tricky balance between comfort and style — a classic men’s sweatshirt for early fall.
- The Denim: Roark Revival 12.5oz. Stretch Travel Denim, $67.98 — Whether you wear the Stretch Travel Denim from Roark Revival for actuall fall travel or a lazy early fall weekend, you’ll look just great doing it.
- The Stylish Leather Boots: Red Wing Iron Ranger Boots in Hawthorne, $315 — As durable and investment-ready a pair of timeless boots as you’re apt to find, the Red Wing Iron Ranger Boots are perhaps the perfect men’s boots for fall. It’s that simple.
- The Belt: Levi’s Contrast Stitch Belt, $26.99 — Never, ever sleep on your accessories — take it from me! The Levi’s Contrast Stitch Belt fits in with the rugged vibe of this ensemble.
- The Durable Field Watch: Hemel Tracker Watch, $340 — A outfit with some hearty, hard-wearing pieces deserves a stylish casual watch — with its blend of bold style and durability, the Hemel Tracker Watch works.
- The Wallet: Wingback London Cash Wallet, $59 — Whether you’re opening up a tab at your favorite brewery or grabbing a casual dinner with your partner, you need a wallet that’s as stylish as you are — seriously.
- The Stylish Socks: CHUP Niyol Socks, $35 — Add some pop — and comfort, and warmth — to your early fall outfit with the subtly stylish CHUP Niyol Socks.
- The Weekened Essential: GrowlerWerks uPint, $28 — Hey, we said this outfit could work nearly anywhere — particularly if you’re sipping on a pint of your favorite craft beer. This pint glass looks great and keeps your beer cold.
- The Grooming Essential: House99 Truly Brighter Eye Balm, $30 — Particularly if you enjoyed a pint or two too many, refreshing your tired eyes is critical — and it’s never been easier than with this essential eye balm from Mr. David Beckham’s new line.
Building an #OOTD for a casual situation can actually be surprisingly tricky — that’s why it’s best to start from the ground up with timeless, seasonally friendly picks that can go the distance, like rugged leather boots from Red Wing Heritage. Add in other easy-to-wear pieces — staples like the Taylor Stitch Jack Shirt and the Myles Apparel Elements Crew — and you’re looking at the makings of an outfit that fits in at Saturday night happy hour or Sunday brunch easily. Comfortable early fall menswear moves such as the Stretch Travel Denim from Roark Revival make it easy to move around and get where you’re going (even if that happens to be your local coffee shop).
I’m also a huge proponent of wearing durable accessories that you can readily mix and match, like the Hemel Tracker Watch and the tough Levi’s Contrast Stitch Belt — both everyday carry essentials that can be used with a host of other fall style ensembles. Focusing on comfort merged with style is also going to yield you some favorable returns, hence the use of the striking CHUP Niyol Socks here. For raising a glass in style (or offering a neat gift to a weekend host), something like the GrowlerWerks uPint is also going to make a lasting impression. Top off your look with a handy grooming essential from House99, and you’re set to take on the new season in style — to say the very least!
That’s all I’ve got for ya today. Thanks for reading!
-Beau