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Aspiring Gentleman’s Guide to Fall Fashion


With the temperatures dropping and leaves beginning to change colors, it’s time to start transitioning your wardrobe to include pieces for cooler weather. Now that Fall is here; there’s no better excuse to revamp your closet and layer up, taking your style to the next level. Whether you’re looking for your next football game outfit or the perfect apple picking sweater, here’s a list of our favorite pieces we’re looking forward to incorporating into our fall wardrobe. 

BOSS 1 - Aspiring Gentleman’s Guide to Fall Fashion

BOSS Turtleneck Sweater

As it gets cooler, you’ll need a cozy sweater to get you through the season. We’re a fan of this turtleneck to stay comfy and fashionable. The wool is thick enough to keep out the elements but slim enough to be a good layering piece still.

Buttercloth Herjavec Collection 1 - Aspiring Gentleman’s Guide to Fall Fashion

The Herjavec Collection by Buttercloth Men’s Dress Shirt

This crimson-toned dress shirt was handpicked by Shark Tank investor Robert Herjavec as a part of his new business casual collection with Buttercloth. It’s the perfect autumn color and feels like your favorite t-shirt while looking sophisticated enough for the office or date night. Buttercloth’s signature long-fiber cotton is also wrinkle-resistant, meaning you can pack this shirt for all your fall adventures without hassle.

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Veja Men’s V-10 Sneakers

What makes these white sneakers stand out is both the intricate white leather detailing on the panels, plus the ultra-luxurious jersey lining. All-white sneakers are a classic wardrobe staple that transition nicely from summer to fall and beyond.

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CUTS Split Hem Henley

Even in your basics, you can add some fashion. One of our favorites this season is the CUTS Split Hem Henley – minimalistic, yet distinctive. Check out the Plum and Laurel Oak colors for a very on-vibe hue.

Daniel Wellington 1 - Aspiring Gentleman’s Guide to Fall Fashion

Daniel Wellington Classic St Mawes

Don’t let Daylight Savings get the best of you. This clean, minimalist watch is perfect for Fall. Once you have this timeless fashion piece on your wrist, you’ll never want to leave home without it.

Orvis 1 - Aspiring Gentleman’s Guide to Fall Fashion

Orvis Wool-Blend Shawl Cardigan

Cardigans aren’t just for your grandfather anymore! This cardigan will give you the warmth of sitting by the campfire and pairs well with a glass of whiskey. 

Alex Mill’s Rugged Cord Sack Jacket

Layers, layers, layers. This dress jacket uses rich corduroy fabric to make a statement while still keeping you warm. Add a scarf to complete your fashion-forward look.

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Tipsy Elves Men’s Tuxedo Socks

Wedding season, anyone? Grab a pair of fun socks to jazz up a suit and subtly show your personality – without taking attention away from the bride. These give new meaning to the term “dress socks.”

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Cole Haan Regular Fit Stretch Wool Coat

Navy, black, and charcoal get a lot of love when it comes to wintertime outerwear. But a steely light gray coat looks equally stylish and will make you stand out in a sea of dark colors.

TAFT - Aspiring Gentleman’s Guide to Fall Fashion

TAFT’s Jack Boot in Grey/Brown

Whether you pair these dual-toned boots with formal attire or casual wear, they will bring a trendy element to your outfit as a wool-and-leather accent piece. The boots are sturdy and ready for any type of weather. 

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