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10 Cozy Yet Sleek Items That Make Fall Your Most Stylish Season

Aug 06, 2023

Every product was carefully curated by an Esquire editor. We may earn a commission from these links.

Feel that chill in the air?

It's a well-known fact amongst stylish guys that fall is the very best season for fashion. Tucked between the sweaty, sweltering summer and the bone-chilling, pile-on-the-coats winter, autumn means cozy knitwear, light jackets, jeans, boots, rich colors, and maybe even a hat or a scarf. In other words, the sartorial middle ground that we long for all year round. Add the fact that autumn is a time for heading outdoors for leaf-peeping, hikes (in the country), or neighborhood strolls (for you city folks), and it's a great time not only for dressing well, but for those outfits to be seen.

Still, as we do the seasonal changeover, perhaps you feel like something's missing. Maybe you culled a favorite sweater or flannel shirt in the spring cleaning and now there's a hole in your wardrobe. It happens to the best of us. And, of course, that simply means you have a gap in the closet that needs filling. Which is where Amazon comes in, to make buying a much-needed pair of jeans or a sturdy pair of boots that much easier. We've done the legwork for you, finding the 10 top items that will get you through the season and beyond.

Yes, we love a plain crew-neck sweater as much as the next guy, but nothing—and we mean nothing—says fall quite like a chunky, textural cable knit. This one has a slim fit, which gives it a cool, modern edge. Pair it with jeans and boots and toss on a quilted vest and, bam, you're ready to take on the day.

Loafers have been trending for a year or two, and it's plain to see why—they're both easy to wear and versatile, and add just the right amount of class to an outfit. These classic ones are made from a rich suede for the ideal touch of texture and deep color to elevate a familiar staple.

Every guy needs a substantial sweatshirt to layer on over a T-shirt and under a coat. This zip-up comes with built-in durable workwear street cred in an array of colors. We opt for black because it looks great with everything.

Perfect for weekend days and WFH scenarios, a pair of sweats makes a fall wardrobe complete. They should hit at the ankle and have a tapered cut to avoid looking schlubby. Pair them with something unexpectedly dressy, like a cashmere sweater or a lightweight chore coat.

Aviators are a timeless shape that look good on just about any face and go well with a wide range of sartorial sensibilities, from classic to trendy to streetwear. The brown tortoiseshell color and the tinted ombré lenses add up to a nice seasonal update.

The long-sleeve T-shirt is a workhorse. Wear it on its own with jeans or corduroys, under a hooded sweatshirt or vest, with gym shorts on a quick errand run, or even with a well-tailored suit for an unexpected relaxed take on your workday uniform. Is there anything a long sleeve can't do? Not really, no.

On the list of fall wardrobe must-haves, a pair of jeans is at the very top of the list. From casual to dressy, from office to off-duty, a pair of jeans makes anything and everything look better. These, with their easy, relaxed cut and smart blue shade, will work in a variety of outfits and seasonal situations.

This utilitarian boot can go the distance. It's subtle enough to work with a variety of looks and is truly timeless. These guys will take you from fall into winter with ease, rain, snow, or shine.

The devil's in the details, as they say, and that means you gotta be thinking of everything when it comes to a perfectly balanced outfit, including the belt. This one is a classic with a twist. It's one of those subtle things that will really stand out and show others that, when it comes to style, you think big-picture but are detail-oriented.

While we've got a closet filled with them, this muted, laid-back plaid shirt is a welcome addition to our rotation. Wear it untucked with some jeans or even tucked into some smart khakis, if you’re at one of those more low-key offices. Toss a sweater over it when it gets cooler or wear it on its own—a piece like this goes the distance.

Berlinger is a freelance writer based in Brooklyn. His work has been featured in the New York Times, Bloomberg Businessweek, the Los Angeles Times, the Business of Fashion and others. He’s probably wasting time on Twitter right now

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