For some, it’s the colorful leaves, the crispness in the air, or the sudden profusion of pumpkin spice, but for us, the best thing about fall and winter is finally pulling our favorite sweaters out of hiatus.

As timeless as denim and cozier than grandma’s quilt, sweaters are a time-honored addition to any guy’s wardrobe, seeing us through the colder months with a rock-solid balance of style and practicality. Need to dress up a little? Grab a sweater. Temperatures plummeting? Grab a sweater. Hitting happy hour with a few buddies? Again, sweater. When you really think about it, sweaters may just be the most versatile form of cold-weather gear out there.

With such a long and storied history and so many different styles to choose from, picking the right knits for your needs can be daunting. So, to help you navigate the stormy seas of classic men’s sweaters, we pulled together a selection of our absolute favorites. These are the trusty staples we count on to get us through chilly fall evenings and brutal winters. From rugged fisherman sweaters to versatile crew necks and classic cardigans, this guide will supply all the info you need to find the right sweater (or sweaters) for you.

fit model wearing The Harbor Sweater Jacket in Mahogany

The Classic Crew Neck Sweater

The strength of a crew neck sweater lies in its stealthy versatility. With a simple, more fitted design and subtle texture, a crew neck sweater is as at home with boots and blue jeans as it is under a blazer, making it the perfect pinch hitter when you need to add a little insulation to your outfits.

While you can find crew neck sweaters in everything from cotton to Merino wool, texturally nuanced fabrics like the baby yak wool in our Lodge Sweater are a great way to up the visual appeal of an otherwise straightforward look.

fit model posing in The Lodge Sweater in Sand Donegal

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Shawl-Collar Cardigans Are A Wardrobe Multitool

Maturity is realizing that Grandad was right about a lot of things: changing your own oil, rising with the sun, and the value of a good shawl collar cardigan, to name a few.

Cardigans are the Swiss Army knife of sweaters. Throw one over a tee shirt and chinos for a smart casual getup, dress it down even further with sneakers and jeans, or layer it over an Oxford shirt as a stand-in for a sport coat.

Not only does a cardigan go with just about anything, it’s also one of the most comfortable garments you can wear. Thanks to the full placket, throwing it on or taking it off is a breeze, and the thick shawl collar negates the need for a scarf.

For our money, cardigans with a chunkier, more textured knit are the best choice for both style and utility (heftier build = more warmth). With their rich handfeel and classic curb appeal, our perennial fan-favorite, The Crawford Sweater, is tough to beat. And with a wide array of colors to choose from, you can snag one for every day of the week.

fit model sitting wearing The Crawford Sweater in Charcoal

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The Rugged Fisherman Sweater

For most guys, when you think of the word sweater, the image of a fisherman’s sweater is what comes to mind. With their storied history of braving battering waves on the open seas and adorning the likes of Ernest Hemmingway, fisherman’s sweaters are a rugged yet timeless style that’s just as recognizable today as it was a hundred years ago.

While their distinctive chunky knit can offer a touch of sophistication when styled with chinos and sneakers, a fisherman’s sweater falls more into the realm of workwear than it does smart attire. Given their innate grit, we like to wear our fishermen’s sweaters with selvedge denim or double-knees and a solid pair of boots for an outfit that would look at home down on the docks or soaking up the smell of whiskey in Hemmingway’s writing room.

fit model posing in The Fisherman Shawl Sweater in Heather Oat Merino

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Waffle Knits - The Outdoorsman’s Companion

If you’ve got more than one pair of hiking boots in your closet, are faster at tying flies than you are your shoes, or have a mud-covered 4 Runner in the driveway, a waffle knit sweater is probably the option for you.

On top of being damn handsome to look at, that pronounced waffle finish allows more airflow and better sweat dispersion, making these adventure-ready knits an ideal antidote to a cold weather camping trip or treacherous fall hike. If you’re looking for the absolute maximum in rugged practicality, we’d recommend opting for a Merino wool sweater.

While the word “wool” may conjure softness, Merino wool is a natural performance fabric that resists odor, regulates temperature, and can stand up to just about anything you throw at it.

When it comes to wearing your waffle knit sweaters, we find it best to think of them like a beefy big brother to your favorite thermals—casual, easy to style, and sturdy as all get out. Needless to say, we wouldn’t wear this one to a wedding.

For even more utility, add a waxed jacket over to create a warm and weather-resistant outfit that’s as timeless as the woods themselves.

fit model posing in The Sidecountry Sweater in Heather Coal Merino

Shop The Sidecountry Sweater

editorial image of Canyon Creek Cabin
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Model wearing our Slim Jean in Selvedge Denim
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What The Fit?

After years of testing, sampling, and refining, we’ve developed two signature trouser fits—Slim and Democratic—to help customers of all shapes and sizes dress their best. Not sure which one is right for you? No worries, we've got you covered with an in-depth breakdown to help you pick your next favorite pair of pants.

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