#OOTD: How to Wear an Overshirt For Fall

It’s been a busy few weeks when it comes to fall style essentials and surveying the seasonal landscape here at The Style Guide. You might have even noticed a few posts in our new Tuesday Steal series replacing the traditional Tuesday #OOTD slot. But we’re back at it today with a new ensemble, and not a moment too soon for early fall. Let’s get to business. How to wear an overshirt for fall really does start with one of the best men’s overshirts, and the fact that it’s coming at you by way of Flint and Tinder is absolutely a huge bonus. It’s also accented by another stone-cold style essential, the kind of layer you won’t want to leave home without, and that’s one of the best men’s henleys for fall.

Shop an essential fall overshirt now

Today’s #OOTD shows you how to wear it

Now is the time to really let the building blocks of your seasonal wardrobe shine, and that’s where today’s #OOTD comes in. Gone are the days (hopefully) of sweating it out this summer and trying to figure out, say, how to wear chinos in the heat. No sir, fall brings with it some of the best times of the year for layering and for rugged adventure (even if said adventure simply involves a brewery tour and some cold, fresh beer). And of course, that means this look is filled with rich seasonal colors (think faded brown, tan and olive). But it all comes down to the gear itself. I think that you’ll quickly find the Flint and Tinder CPO Shirt Jacket delivers on everything you need in a stylish shirt jacket in this transitional time of year, from the lightweight construction to the durable and functional styling potential. If you’ve been stowing away your “shacket” through the hot summer months, it’s time to let it back out into the open, just in time for the best season in menswear. Let’s get back in the saddle with today’s #OOTD, shall we?

  • The Overshirt: Flint and Tinder CPO Shirt Jacket, $148 — This versatile overshirt, one of the best overshirts for men, is a study in durability and wear-anywhere style potential. It’s made with a blend of cotton and spandex for comfort and stretch in spades.
  • The Henley: Buck Mason Pima Curved Hem Henley, $55 — This won’t be the last time we talk about one of the best men’s henleys for fall. This one is just lightweight enough to layer up comfortably on breezy fall days.
  • The Rugged Fall Pants: Filson Dry Tin 5-Pocket Pants, $135 — You can wear these rugged work pants just about anywhere, from the trail to a distillery or at home around a fire pit. Filson has long delivered the goods, and they continue to do so here.
  • The Boots: Rhodes Footwear Bozeman Boots, $225 — Complete with a well-built moc toe, rich leather and a comfortable-yet-durable wedge sole, these classic moc toe boots are ready for anything this fall.
  • The Watch: Shinola Runwell Automatic Watch, $1,095 — What’s not to love about this handsome, heritage-worthy leather watch? It’s more suited for weekend outings than rough-and-tumble wear, but you’ll be able to get plenty of use out of it this season.
  • The Hat: Howler Brothers Camp Howler Snapback, $35 — A classic ballcap is the only way to top off this outfit, especially one with a distinctive, retro logo. Throw it on at a moment’s notice to get out the door and hit the road.
  • The Wallet: Satchel & Page Slim Bifold, $70 — Could your everyday carry use a refresh? This elegant, hard-wearing leather wallet for men is just what the doctor ordered. It’ll break in beautifully with everyday use this season.
  • The Everyday Carry: Satchel & Page Slim Mailbag, $475 — No matter what you’ve got to haul (your headphones and a book or laptop, perhaps?), this remarkably stylish leather messenger bag is going to serve you well for years to come.

If you ask me, I’d say this #OOTD does just about everything you could ask of it this season. It’s got versatility and multiple styling options available by way of the two top layers, like a stylish shirt jacket and one of the best men’s henleys for fall. You can wear the henley on its own and keep the shirt jacket handy in your extremely cool, stylish leather messenger bag, for example. And it’s all helped along by the perfect blend of form and function via Filson’s rugged work pants, which can be worn to do actual work as easily as they can be worn to grab fall weekend beers. As I always say, no fall ensemble is complete without the right pair of boots, like the classic moc toe boots shown above from my friends at Huckberry. It doesn’t get any better than boots that can be broken in over time, and the same can be said for your other EDC essentials, like your newfound, supremely stylish leather wallet for men, courtesy of Satchel & Page. Invest in the best and reap the rewards this fall. I’m also of the opinion that you’ve got to keep your accessories on point, and that means finishing this outfit off with the right combination of high and low: An investment-level leather watch, not to mention an eye-catching ballcap. You’re ready for anything between those two fan favorites. Where will this #OOTD take you? Be sure to let me know in the comments below. Stay stylish this fall! 


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