Fall Clothing Essentials for Every Man in 2023

While the right pair of blue jeans can carry you through just about any situation these days (short of black tie affairs, that is), there’s going to come a time when you want to kick back in comfort. It doesn’t have to be sloppy with the right pair of tailored lounge pants, which aren’t intended for athletic wear but rather, are meant for relaxation, thanks to a tapered fit, cuffed elastic ankles and plenty of cool fabric choices.

Taylor Stitch checks the right boxes with an indigo-dyed pair of waffle-weave fabric lounge pants, the kind you can readily wear at home on lazy weekend days but that won’t let you down when you step outside the house, either. The organic cotton fabric is soft and sustainable, too.

If you forewent jeans for much of the summer in favor of rocking some of the best men’s shorts, we don’t blame you. But fall is as great a time as any to embrace timeless menswear staples made modern, like the blue jean. Originally a foundational workwear piece, you can now wear dark blue jeans at the office, over the weekend and on the road with buttondown shirts, henleys, cardigans and many more staples.

Mott and Bow in particular gets things right with the inky blue of the Crosby Jeans, made with comfortable stretch fabric (but not too much!). Helpfully, they’re available in a Straight fit that flatters every guy. Note that the brand also delivers other shades of denim in Slim and Skinny fits at agreeable prices.

Not sure where to start your fall menswear search? Start with a crucial top layer, and don’t be afraid to mix things up. If you’ve never tried out a waxed trucker jacket, or a trucker jacket in general, just know that the style is like a more souped-up, yet no less casual, take on the denim jacket, but it’s often made from weather-repellent waxed cotton.

It’s hard to go wrong with the legendary Flint and Tinder Waxed Trucker Jacket, even if you’ve never worn one. It goes well with jeans and a henley, it wears nicely with a chambray shirt and chinos, it comes in a range of colors to suit every style, and it’s even lined in warm flannel for especially chilly days.

A henley is practically the ultimate rugged fall style choice (although we think the rest of our fall clothing essentials also fit the bill nicely). The henley is visually appealing thanks to the button placket, which means you can wear it as an undershirt beneath a waxed trucker jacket or on its own–since it looks more interesting than a regular long-sleeve tee. Plus, it’s a warm base layer that’s not too overwhelming when made from the right fabric.

Free Fly definitely knocks it out of the park when it comes to fabric, using a flexible blend of bamboo fibers for warming insulation and temperature regulation in equal measure. Colors like Heather Black wear well with shades of navy, grey, olive, maroon … you name it, and the right henley can get the job done.

What’s more fitting for fall than a flannel shirt (say that five times fast)? Cotton flannel is soft, warming and durable, trusted in everything from shirt jackets to blankets to plain old classic flannel shirts. There’s a reason your grandpa stocked his closet full of ‘em for the colder months–flannel shirts are certainly worthy of inclusion on any list of the best fall clothing essentials.

Luckily, Line of Trade (an in-house brand at Bespoke Post) has managed to harness the right blend of vintage durability and modern style with the Summit Flannel Shirt. Take your pick from four sharp, retro-leaning plaid patterns across a spectrum of sizes, and rest easy knowing that you can rock this shirt on its own or as a top layer over your favorite henley.

Chore coats occupy a unique spot in the menswear world. Some chore coats are made from hefty waxed cotton and are often bulky and designed more like a field coat, with a longer cut and button pockets. Some are more of a hybrid style in nature, more like a cross between a shirt jacket and a traditional chore coat. We think your wardrobe needs a touch of both, but with warmth and style in mind.

That leads us to Buck Mason’s take on the chore coat, which bridges the gap between a patch-pocket blazer and an old workwear-style coat, complete with plenty of room for your everyday carry essentials. Wear this heavy-yet-soft wool coat to the office or wear it out and about with the collar gently upturned–or bring it on a camping trip for brisk fall mornings. It’s one piece that can do a bit of everything.

Here at WERD, we’re of the mind that men’s fall clothing essentials are the pieces that bridge the gap between two distinct styles with versatility in mind. Take the shirt jacket, or shacket. It often looks like your favorite flannel shirt on the surface, but it’s usually cut from heavier fabric, occasionally features an added layer of insulation and often boasts a roomier fit to layer atop a thermal shirt or even… another shirt, like an Oxford shirt.

Relwen goes all out with its Quilted Shirt Jacket, as the Ohio-based brand should given the surrounding weather. The outside is soft brushed cotton flannel twill, like a trusty shirt, but the inside is amped up with recycled polyester insulation for plenty of fall-friendly warmth.

The list of options when it comes to the best fall boots is nearly endless, is it not? But as with our other top picks for the best fall clothing essentials, we think versatility reigns supreme. While you could go with a rugged pair of slip-on work boots or a set of hefty moc toe boots, a pair of well-made lace-up boots with a sturdy sole, a crisp captoe design and goes-with-anything dark tan leather are always a solid bet.

That’s where the Portland Boots from Huckberry come into play. They’re sleek enough to wear with tailored chinos, but dressed-down enough to pair with jeans in shades of grey, black or blue (yes, black and tan work together!). Plus, you can even use them to give a wool suit a bit of rugged edge for fall and winter. Best of all? They’ll get better the more you wear them, molding to your foot and aging nicely over time.

Just as with fall boots, any potential rotation of the best fall sweaters has nearly limitless options. When in doubt, it’s best to go with a classic, the kind of sweater you can throw on over everything from a crisp white Oxford shirt to a soft cotton tee for casual weekend style. A navy crewneck sweater can do both of those things, especially one made from easy-to-layer 100 percent cotton.

In the hands of J.Crew, all the details are taken care of, from sturdy ribbed wrist and hem cuffs – for a secure fit – to crisp color options, like Navy, that you can style with just about anything you own (yes, even a pair of faded blue jeans). This sweater shouldn’t prove too stuffy, and the fact that you can wear it with lounge pants or with slim chinos is a major bonus. Don’t forget that it retails for under $80 based on the color you select.