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How to Transition Your Wardrobe to Fall

mens fall fashion
Will Swann

Every year like clockwork, something in the air seems to change. For some, the school bell rings for the first time in months, indicating the end to a glorious summer of mischief (and perhaps love). For others, the weekly trip to the grocery store is now met by an aisle filled with ghouls and goblins. The nights are getting cooler, the days are getting shorter, and that plaid shirt you’ve been staring at since June is nearing re-introduction into the world. Ladies and gentlemen, fall is coming.

Growing up, the return of school was always an excuse to get a new pair of shoes and a few choice articles of clothing to start the year fresh and ideally impress the masses. At an adult level, the cooling temps certainly present a totally feasible reason to update the wardrobe with some longer sleeves, denim, and a pair of size 10s — not that you need a reason to pick up some fresh threads.

From head to toes, here’s how to transition your wardrobe to fall:

You’ll need a cap to complement all your outfits as you transition from summer to fall. One that will outlast the final days on the beach and embrace the changing temps, and if you’re lucky enough, welcome the first of the flurries. The Alive and Free Co. Blood, Sweat, and Beers Trucker Snapback is the perfect addition to any freshman’s overnight bag and any of you older gents looking for a stylish black mesh back, this one is refined with the badass mentality of a hammer and anvil.

However, if you’re one that can start the day with a beanie and maintain a comfortable temperature as the morning dew starts to subside and the sun reaches its point directly overhead, the Coal Mesa is a fine-knit merino wool beanie that will transcend from mountain peak to coveted coffee shop two-top. It can be cuffed or unrolled into whatever you consider to be the perfect look.

Moving down past the neckline to cover your core, you’re going need a long-sleeve button-down to set you apart from all those Chads, Brads, and Thads. The Everlane Modern Flannel is 100% cotton with two button closure flap pockets and a blue crossfade that calls out, “Timber!” It’s a great shirt to start the day in, lay over the backrest as things heat up, and throw back on as the laptop closes.

If you think plaid is played, there are plenty of other options, like the Volcom Caden Solid that is pure black in all its glory. With a single Stone embroidered pocket, novelty buttons, and a modern fit, this long sleeve is perfect for the office, a few at happy hour, or strolling through the later hours as the questionable characters spill out of the bar and embark on the journey home. 

With the leaves falling, so should be your inseams. The Iron and Resin Enduro Denim Jeans are American made from the mills of North Carolina, with the daily battle of life at the forefront of its design. With space-age materials woven into the denim, Iron and Resin built a pant that might just outlast you and anyone’s floor they end up on.

The Freenote Cloth Avila Slim Taper is another great option to leave onlookers star-struck with a Red Wing Heritage leather patch, custom black herringbone pocketing, and 14-ounce natural indigo that would even excite Denim Dan. They come from the mills of Japan and look riveting with a blazer, classic white tee and/or any shirt you pull from the closet.

Just like Nelly and the St. Lunatics told the world that two pairs are better than one, the changing of seasons opens the door to picking up a couple of pairs of your own. The Six Hundred Four Kristensens are a pair that almost no one else will have and are premium laser-etched Italian leather — yeah, laser-etched. Their exclusivity is engraved in the sole and for each of the four colorways, under 200 pairs have been made.

And with the fall, out come the boots. The TAFT Saint Boot is simply fantabulous and handcrafted down to the final stitch. The leather is hand-painted, making every single pair a unique piece of art. The calfskin lining topping the stacked leather sole provides comfort otherwise only found in Hefner’s smoking jacket. These boots go beyond topping the pedestal and are simply too legit to quit.

Oh, a jacket. Almost forgot, summer has been too long. Flint and Tinder’s Flannel-Lined Waxed Trucker Jacket is weather-resistant (hey Pacific Northwest, this one speaks to you), has an internal media pocket, and you better believe it was crafted in the U.S. of A.

The flannel lining may be a little much for some, but that’s why Taylor Stitch’s Ojai Jacket is the perfect complement to any fall outing. The Ojai Jacket is 100% cotton with an exclusive Arid Camo finish to help to duck into cover as needed when the leaves fall. It’s a great piece to start the day with, assuming you have a strong layering game.

Don’t be the last apple to fall from the tree this fall, whether you need to update your apparel or not. The changing seasons give a reason and excuse to fill the shopping cart with a handful of items that will keep you nice and toasty, while looking showstopper good as Mother Nature closes the beach. All you’ll really need to do is decide if the forthcoming heat bill is more or less important than a new pair of denim or boots.

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Former Digital Trends Contributor
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