Stroll Into Fall in Style With Some of Our Favorite Men’s Fashion Pieces

men's fall fashion
Courtesy of J.Crew
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Now that Labor Day has come and gone, cooler weather is just around the corner. While we wait for those temperatures to drop, now is the perfect time to go ahead and stock up on pieces that can seamlessly transition you from summer to fall to winter.

Fall is an opportunity to have some fun with fashion and layer multiple pieces; the chance to play with different kinds of textures and looks. But if you feel like the whole process is pretty daunting, don’t worry, we’ve got you covered.

Below, we’ve rounded up 12 of our favorite pieces that you’ll need to have a stylish fall. And, to make it even easier, we’ve scoured the internet for socks, shoes, pants and shirts, to keep you covered — literally — from head to toe. So grab that pumpkin spice latte and settle in for your most stylish fall ever.

1. Kingsman Herringbone Cotton-Blend Socks

A good statement sock is a quick and easy way to convey to others that you know what you’re doing when it comes to fashion. This pair, developed in partnership between online retailer Mr. Porter and the Kingsman: The Golden Circle film (yes, you read that correctly), brings many of the looks actually seen in the 2017 sequel directly to consumers to purchase. The herringbone is a pattern that’s not too flashy, but has just the right amount of style to draw attention to yourself in the best possible way. Plus, if they’re cool enough for the Kingsmen, they’re definitely cool enough for you.

Kingsman herringbone socks Courtesy of Mr. Porter

2. J. Crew 484 Slim Fit Chinos

Few brands do chinos better than J. Crew, so they naturally deserve a spot on our list. With a cornucopia of colors befitting of fall’s lovely hues (thinking browns, forest greens, and greys), there’s most likely a version here that you don’t already own. The tailored, slim fit also has just a touch of elastic in them, so you won’t need to worry about them being too snug.

j crew 484 slim fit pant Courtesy of J. Crew


3. Banana Republic Long-Sleeve T-Shirt

It never hurts to have a clean, reliable basic long-sleeve t-shirt like this offering from Banana Republic. Black tees go with everything and are super useful to layer under a sweater, jacket, or even a sport coat. Made from a high end cotton that feels as rich as it does cozy, it’s bound to be one of your favorites.

banana republic long sleeve t Courtesy of Banana Republic


4. Schott 50s Perfecto Leather Biker Jacket

A classic leather jacket never, ever goes out of style. Which is why investing in a piece that fits — and fits well — is a great decision. Moto jackets have always been popular and Schott makes some of the best in the world. Take, for example, this 1950s style (think Brando in The Wild One) jacket that’s just as cool now as it was back in that era. A slim fitting jacket that hugs you in all the right areas, you’ll be the spitting image of a Hollywood movie star, looking — and feeling — like a million bucks.

schott leather biker jacket Courtesy of Mr. Porter


5. Nike Killshot 2 Sneaker

What we love about the Nike Killshot is that they’ll look just as good in a casual office setting as they do when you’re running around town on a weekend or out on a date. A perfect low profile sneaker, the various contrasting touches (whether it’s the cripsy gum sole, the suede patches, or that vibrant Nike check) all build to something that’s never too much, opting instead for just the right amount of each part. The final result is a striking looking sneaker that’s perfect to wear all season long.

nike killshot 2 Courtesy of J. Crew


6. Mr. P Wide-Leg Cotton-Corduroy Pants

After several years of slimmed out pants, things are starting to widen back out. If you’re feeling adventurous, these wide-leg pants made for Mr. Porter as part of their exclusive Mr. P line; made from a heavy-duty corduroy (perfect for cool fall weather) and wide without being too much. It’s a good gateway piece to see if you feel like playing around with a new look. Plus, the Mr. P line offers designer quality looks and fits at a price that isn’t quite as scary as some other designer brands.

mr p courdory wide leg pants Courtesy of Mr. Porter


7. Polo Ralph Lauren Slim-Fit Cashmere Sweater

Once you get a sweater in cashmere, there’s no going back. Equal parts soft and warm, cashmere is also extremely lightweight, which makes it a great piece for layering: Throw it on top of a nice oxford button down shirt and then toss over a jacket and you’ll be prepared for the majority of cold weather that comes your way. Plus, this turquoise isn’t too garish of a hue and works great to incorporate a bit of color into what’s often a rather drab and dearly couple of months.

Polo Ralph Lauren Cashmere Sweater Courtesy of Mr. Porter


8. Red Wing Moc Toe Boot

Every man needs a classic set of boots — and there are few brands that do it better than Red Wing. Their moc toe boot is a classic menswear mainstay, seen on the likes of Ryan Gosling, and will hold up to all kinds of wear and tear. Rugged and built to last, they’re a boot you’ll feel just as good about buying as you do wearing them.

red wing moc toe boot Courtesy of Nordstrom


9. J. Crew Slim Fit Oxford Plaid Shirt

While you may have some standard Oxford button-down shirts, snapping up a plaid option is a great way to refresh your look. Instead of the typical red and black buffalo plaid print, we prefer this green, black, and navy option that’s a great fit for fall colors. The black in the shirt will pair well with a black leather jacket, while the blue and green could go great with jeans. Plus, J. Crew’s slim fit shirt is just the right amount of tailored, meaning you’ll look great from the moment you put it on — no alterations needed.

jcrew slim fit Kansas green button down Courtesy of J. Crew


10. Grenson Suede Penny Loafers

A suede penny loafer is just one of those timeless bits of menswear that every guy should own: they have a simple, yet elegant design that feels refined and classy. Plus, they’re likely to pair well with almost everything else you already own, looking just as good with jeans as they do with a dress pants or even a suit. While this pair from Grenson is maybe a bit more than you’re used to paying for dress shoes, it’s absolutely worth spending the money on this particular pair. Their construction makes it so as soon as the sole wears thin, you can take it get it replaced with ease. Just be sure to take care of the soft suede and you’ll be set for a long while.

grenson penny suede loafer Courtesy of Mr. Porter


11. John Elliott Cast 2 Slim-Fit Denim

Along with a lot of trends seen in the late 60s and early 70s, lighter wash denim is in vogue right now. Due to their popularity, it’s easy to find a good pair, but a little bit more difficult to find a great pair — or it was until Los Angeles-based designer John Elliott dropped his version. Each pair of denim Elliott creates takes about a year (!) to create, as every single pair must be cut and dyed just right to provide only the highest quality. The Cast-style is the designer’s slim fitting jean that’s crafted from premium Japanese denim to ensure each pair is sturdy enough to be long lasting. The last flourish is that vintage, lived-in looking wash (known as the “Coast”) that makes it such an attractive pair.

john elliott cast denim Courtesy of Mr. Porter


12. Levi’s Denim Trucker Jacket

Western vibes are absolutely in for this fall, so making sure you have a denim jacket is a must. And while there are plenty of luxury options to splurge on, sometimes it’s best to just shut up and play the hits. With that in mind, this classic Levi’s Trucker jacket is tough option to beat. Quality, at a price that’s not too overwhelming, makes for an accessible option for nearly everyone. The black color will go with everything you already own, but also don’t be afraid to pair it with your jeans (with the John Elliott jeans we recommended earlier, perhaps?) for a trendy look that is sure to turn a few heads.

levi denim jacket Courtesy of Nordstrom


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