17 Best Men’s Fall Fashion Pieces for Staying Warm & Stylish This Season

Fresh Fits

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Fall is the perfect time of year to explore a new, re-invented look, whether you’re picking out stylish street wear or building up a professional wardrobe for the office. Master a layered look that’s neutral enough for all settings, but still add in those important statement pieces, and you’ll have a signature style you’ll love.

Jordans give any man some swagger in his step, and these eye-catching colors can make an otherwise subdued look pop. Versatile and stylish, all streetwear wishes it could be as effortlessly cool as a clean, new pair of these sneakers.

Jeans are the foundation for a wide range of casual looks, so getting a pair that’s durable, comfortable, and best of all affordable, will set you up for a winning look all season. These extreme stretch jeans marry a functional range of motion without being the men’s version of jeggings, so you can jump, kick, and crouch without blowing out the knees of your new favorite jeans.

If you’re going to drop big-label dollars, splurging on a signature piece that makes a statement is the way to go. A leather jacket will last forever if properly cared for, and the classic cut and fit on this aviator by Diesel gives it a timeless, almost vintage look.

The casual look of Toms has been upgraded to office-appropriate style with these lace-ups. Available in sizes 7-13 and with nine color choices, they offer a versatile range of looks, while still doing good for the world at large with their shoe donation program.

Make sure that your layers add texture, color, and contrast to your outfit. Amazon’s Goodthreads brand sweaters are well made but inexpensive, so you can pick up a range of colors and styles. Available through Prime Wardrobe, you can order a variety of choices and try them on at home, so you’re able to see them with the rest of your clothes before committing.

Target’s house brand Goodfellow & Co™ jeans are breathable and have plenty of room to move, at a price point that gives you room to stock up on multiple pairs. With a range of fit options from skinny to athletic to bootcut, you can experiment with new styles and find the perfect fit your your body type.

Stylish enough to be streetwear, these North Face boots are trail-approved, so you can count on them going the distance for you whether you’re city commuting or communing with nature. Ideal for icy streets, they’ll help keep you on your feet when the terrain gets tough.

High-end formal wear can make special occasions unforgettable, so if you’re dressing up for a winter wedding you can’t make a better investment than a stunning jacket. Burberry marries English styling with Italian construction for this wool jacket with velvet collar and buffalo horn buttons, and it’s a showstopper.

These custom monogrammed cufflinks will put the finishing touch on any outfit for a formal occasion. Available in a range of metal finishes and font choices, personalizing your accessories is a way to show ownership over your style down to the smallest details.

100% wool, this boldly colored scarf is soft and decadent, with a vibrant color pattern and a gender neutral wrap length. Available in a range of color options, a pair of scarves make for a perfect his-and-hers gift for the holidays.

Made of 100% Supima cotton, this mock turtleneck fits snugly, so it’s a perfect layering piece for office wear or dates. Pair it with a dress blazer for a formal look, or layer under knits for a touchably soft look that’s perfect for dinner and drinks.

Stay warm even when the temperatures drop without sacrificing style points. These 100% Merino wool dress pants come in four colors and size 32 to 42 waist, with custom hem and cuff options to ensure they are perfectly tailored to fit.

Be prepared for a spur of the moment getaway with this leather duffel bag from Fossil. Perfect for a boys weekend or a couple’s escape, it’s easy to keep organized with external pockets that give you room to carry a wallet, keys, tickets, or other travel essentials.

If you’ve been coasting by on an existing wardrobe too long, it’s time to refresh your basics. Toss anything stained, holey, or the wrong size, and re-evaluate what you need for day to day. If your job has changed and a more polished look is required, these oxford dress shirts bring a simple sophistication to office wear, and are available in big and tall sizes. The extra-long tail ensures that these will stay tucked, even if you have to move frequently at work.

Accessories pull an outfit together, conveying whether a look has been well-considered and polished, or thrown together last minute. Even a casual piece, like this fun and stylish minimalist watch, can anchor an outfit.

While winter may require a glove so warm and waterproof that it simply can’t be stylish, these leather driving gloves don’t suffer the same fate. A vintage look and a range of dye options make these an instant classic, while also protecting your skin from the chills of fall.

It’s easy to stop wearing eye protection when the beach weather stops, but a good pair of sunglasses is a year-round accessory. From snowy slopes to sunny days, you’ll look great and suffer fewer light induced headaches with these well-made shades.


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