THERE’S SOMETHING ABOUT the turning of the leaves and that first fall chill in the air makes us want to dress like we’re hiking the backwoods of Maine, even if we’re just stepping out for a cup of coffee. That’s why Men’s Health’s 2024 Fall Style Guide is highlighting apparel that can handle the great outdoors that look stylish enough to wear on a daily basis. We’re talking rugged classics like flannel shirts and wool sweaters that play well with outdoors staples like tech pants and packable down vests, plus plenty of shackets!
The Men’s Health fashion team field tested dozens of pieces to assemble a collection that handles cold city streets and windy mountain peaks with equal durability, warmth, and—above all—style.
Check out the best fall and winter clothing for men below, chosen by our fashion director Ted Stafford, and worn by Saturday Night leading man Dylan O’Brien.
Base Layers
![dylan obrien](https://i0.wp.com/hips.hearstapps.com/hmg-prod/images/hlh110124lifestyle-006-67116dd3583c5.jpg?resize=870%2C1160&ssl=1)
Whether you’re on a chilly morning run, or just lounging around the house, this longsleeve merino crewneck is deceptively soft and warm. It provides all the warmth of a heavy jersey sweatshirt in a much lighter weight package. Plus, merino wool has superior breathability and moisture regulation.
Smartwool is a brand that puts fabric first and foremost, which means high performance and even higher durability. This merino crewneck will keep your body heat locked in as a base layer on a hike, and show off your hard-earned gains on a night out.
Waffle knit thermal shirts have such a rich history that they will never go out of style and look great with a massive range of looks. Buck Mason makes an excellent reproduction of the military surplus models that made the style iconic in the mid-twentieth century. Try it under a leather jacket or over your favorite flannel shirt.
Patagonia built this long sleeve tee for endurance activities, with excellent moisture and body heat regulation. It is an excellent base layer for endurance activities like long distance hikes and chilly weather cycling. Sweat disappears quickly and washing is a breeze thanks to a super fast drying design.
Flannel Shirts
![dylan obrien](https://i0.wp.com/hips.hearstapps.com/hmg-prod/images/hlh110124lifestyle-001-66fe9e73f37b5.jpg?resize=870%2C1160&ssl=1)
This flannel from Todd Snyder has a secret ingredient that is typically found in summer button down shirts. It’s Viscose that has been blended with cotton to make a silky soft and light fabric. This wears more like a dress shirt than a lumberjack uniform, and looks extra sharp with a tie.
The Alaskan Field Guide Shirt from Filson is your grandfather’s flannel, and we mean that in the best way possible. Everything we love about this top—the warmth, comfort, durability, and functionality—revolves around the burly cotton twill fabric. Like a good pair of jeans, it will just get better with age.
Uniqlo teamed up with J.W. Anderson for a capsule collection, and made an incredibly versatile flannel shirt. It has a single patch chest pocket, which gives a slightly dressier look than traditional double pockets. It is a perfect piece for cold weather layering.
Wool Sweaters
![dylan obrien](https://i0.wp.com/hips.hearstapps.com/hmg-prod/images/hlh110124lifestyle-004-66fea15a3dbe2.jpg?resize=870%2C1088&ssl=1)
Think of this mockneck sweater from Ralph Lauren as a refined alternative to a quarter-zip. The speckled texture and slightly chunky knit blend perfectly with an oxford shirt and corduroy pants. Don’t worry about a scratchy wool feel because this sweater is made with nylon and silk for a smooth touch.
J.Crew is a heavyweight in the field of cozy fall sweaters, and this bird’s-eye crewneck is as classic as it gets. It is a great pattern to layer under a denim jacket or peacoat. Dress it down with some joggers and running shoes, or up with dress pants and loafers.
A thin merino wool crewneck sweater is a business-casual and semi-formal essential for the fall and winter. Banana Republic offers one that fits just right, half-way between slim and classic. Wear it with a pair of dark jeans, or suiting slacks with dress shoes for an easy and put-together look.
Shackets
![dylan obrien](https://i0.wp.com/hips.hearstapps.com/hmg-prod/images/hlh110124lifestyle-007-67116e7e0f4b1.jpg?resize=870%2C1160&ssl=1)
This is hands-down the most luxurious shirt-jacket we’ve ever worn this year. This cashmere beauty looks and fits like a boxy two-pocket shacket in a brown buffalo plaid. But the fabric is so buttery soft, and has a beautiful texture up close.
Try a modern take on the shirt-jacket with this tech infused version from Lululemon. The polyester fabric is stretchy, sweat wicking, and quick drying for athletic performance. But this piece is better suited for long days at the office and long nights around a campfire.
Heavy twill button down shirts like this come with nearly endless styling possibilities. The simple two-pocket design and neutral tan color can carry an outfit with jeans and t-shirt, or make a clean base for a down vest, plaid scarf, and wool beanie. There are no wrong answers here.
More jacket than shirt, this sherpa-lined top from Faherty is as warm and cozy as a sleeping bag. The high pile fleece provides tons of insulation and cushioning, and the cotton-wool exterior is soft to the touch. Hang this one by your front door because you’re going to want easy access to it all fall.
Down Vests
![dylan obrien](https://i0.wp.com/hips.hearstapps.com/hmg-prod/images/hlh110124lifestyle-003-66fea0be62664.jpg?resize=870%2C1088&ssl=1)
Parkas
![dylan obrien](https://i0.wp.com/hips.hearstapps.com/hmg-prod/images/hlh110124lifestyle-002-66fead7103188.jpg?resize=870%2C1087&ssl=1)
The Langford Parka is literally designed to survive Antarctica, so it’s plenty warm enough for anywhere in the lower forty-eight states. Cargo space is another benefit to this heavy duty winter jacket, with four exterior and three interior pockets.
The Patagonia Windshadow parka does everything you need a winter jacket to do. The DWR treated shell is fully waterproof and has strong wind resistance, which is especially effective when the high-zip hood is cinched down with an easy access drawcord.
Tech Pants
![dylan obrien](https://i0.wp.com/hips.hearstapps.com/hmg-prod/images/hlh110124lifestyle-005-66feae876a346.jpg?resize=870%2C1088&ssl=1)
What looks like a common chino, is actually an ultra flexible tech pant from Banana Republic. Upgrade your office performance and everyday comfort without anyone being any the wiser.
This jogger from Smartwool is built from a hightech, wool based fabric that is weather resistant, breathable, and warm. It is a great casual pant for the coldest part of the year, and styles just like any other jogger in your wardrobe.
What’s so special about this rugged cargo pant from Stone Island? It’s where the materials come from. Recovered cotton is used for the fabric and pigments pulled from recycled materials is used for the dye. The stylish straight leg fit and comfortable drawstring waistband are great for everyday wear.
Shop More of Our Favorite Fall Essentials
Best Fall Jackets for Men | Rain Jackets | Best Chinos for Men | Best Leather Jackets for Men | Best Boots for Men | Best Jeans for Men
Ted Stafford is the Fashion Director of Men’s Health. He oversees all style and fashion content for the brand, and also styles their fashion stories. His active lifestyle informs his passion for translating great designs into real-life style, a favorite part of his job. Prior to joining Men’s Health he worked at GQ magazine and Calvin Klein