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Step into the season with fall footwear for men that perfectly blends style and comfort. From beach to street styles, our collection offers fresh new styles to elevate your autumn wardrobe. Discover your look with on-trend designs and functional fits that keep you looking effortlessly fashionable. Whether you're in search of new arrivals or the most wanted styles, Tillys is your destination for top-rated looks that make a statement. Embrace the cooler weather with confidence and let our trendy styles carry you through every adventure.

$84.99

A premium black canvas sneaker with OrthoLite insole, high gloss eyelets, and 1970's heritage details.

$129.99
Now $90.99 (30% Off)

SALE!

A sophisticated black hiking boot with premium leather, recycled fabric lining, and durable rubber outsoles.

$149.99

A classic brown leather boat shoe with hand-sewn construction and a durable rubber outsole.

$80

A versatile grey sneaker with a breathable knit upper, suede heel, and lightweight EVA outsole.

$159.99

A versatile brown boot with EVA-blend foam cushioning, premium leather, and recycled fabric lining.

$80

A versatile sneaker featuring a breathable knit upper, suede heel, and lightweight EVA outsole.

$158.99

A classic brown waterproof boot with full-grain leather upper, EVA midsole, and durable Surface CTRL™ outsole.

$118.99

A versatile, lightweight hiker with a breathable recycled upper and high-rebound EVA midsole for comfort.

$148.99

A waterproof boot with recycled canvas, leather collar, and rubber outsole for comfort and stability.

$144.99

A waterproof black boot with eco-conscious materials, superior traction, and extra-cushiony interior.

$134.99

A dark brown waterproof chukka boot with premium leather, OrthoLite® footbed, and superior traction.

$89.99

A retro-inspired shoe featuring a durable grey and white EVA upper with a wider toe box for comfort.

$159.99
Now $95.99 (40% Off)

SALE!

A waterproof boot with premium leather, recycled fabric, and superior traction for trail comfort.

$169.99

A taupe suede clog with a cushioned soft footbed, adjustable strap, and lightweight EVA sole.

$169.99

A mocha suede clog with a soft footbed, adjustable strap, and lightweight EVA sole for all-day comfort.

$154.99

A versatile, adventure-ready shoe with camel leather uppers, waterproof technology, and superior insulation.

$89.99
Now $59.97 (33% Off)

SALE!

A durable black and brown skate shoe with suede reinforcements, mesh panels, and rubber underlays.

$69.99
Now $44.97 (36% Off)

SALE!

A vibrant, jacquard-patterned slip-on with a water-repellent textile upper and cushioned ankle collar.

$174.99
Now $124.97 (29% Off)

SALE!

A stylish, waterproof sand-colored boot with leather body, suede tongue, and CUSHGRIP™ outsole for durability.

$139.99

A classic black leather oxford shoe with iconic yellow stitching and air-cushioned sole.

$169.99

A classic 8-eye black leather boot with air-cushioned sole, yellow stitching, and grooved sides.

$99.99

A black suede chukka boot with a warm Teddy fleece lining and slip-resistant rugged outsole.

$84.99
Now $76.49 (10% Off)

SALE!

A black and white skate shoe with a durable upper, Geofit collar, and customizable tongue.

$129.99
Now $90.99 (30% Off)

SALE!

A brown waterproof shoe with Premium Leather, Gripstick™ rubber outsole, and OrthoLite® footbed for comfort.

Fall Footwear For Men

When the leaves start to turn and the air picks up that signature crispness, it’s time to swap out those summer kicks for styles that step up to the season. Fall is all about layering—your wardrobe and your footwear. Whether you’re heading out for a hike in the hills, meeting friends for a coffee run, or just looking to upgrade your everyday look, the right pair of mens fall shoes can make all the difference. Think about those early September mornings when you’re hustling to class or work, dew still clinging to the grass and a chill lingering in the shade. That’s where mens fall boots come in—offering a blend of rugged function and street-ready style that’s built for everything from spontaneous road trips to lazy Sunday strolls. For those who live for the weekend, men fall shoes are the go-to for bonfire nights, tailgates, or just kicking back on the porch with a hot drink. And if you’re looking for a gift that feels both practical and personal, a fresh pair of fall boots men love is a choice that’s always in season—perfect for birthdays, back-to-school surprises, or just because.

Shopping for men shoes for fall isn’t just about finding something that looks good (though style points definitely count). It’s about dialing in comfort, durability, and versatility for whatever your day throws at you. Picture this: you’re navigating wet sidewalks after a surprise rain, crunching through piles of leaves on campus, or dashing from class to a late-night hangout—your shoes need to keep up. Look for pairs with sturdy soles that can handle slick streets, cushioned insoles for all-day comfort, and materials that strike the perfect balance between breathable and weather-resistant. A classic pair of boots works just as well with jeans and a flannel as it does with joggers and a hoodie, making them the MVP of transitional weather. If you’re all about that California-cool vibe, slip-ons and sneakers in rich autumn colors give you the freedom to move from the beach to the city without missing a beat. And don’t forget—fall is a time when everyone’s style gets a little more creative, so don’t be afraid to try new textures, unexpected color pops, or details like contrast stitching and chunky soles. Whether you’re shopping for yourself or searching for the perfect gift for your brother, partner, or best friend, there’s something special about stepping into the season with a pair that just feels right.

Fall footwear is more than just a seasonal swap—it’s a statement about how you move through the world when the days get shorter and the adventures get cooler. From weekday commutes to weekend escapes, the right shoes are the foundation for every fit. If you’re on the hunt for styles that mix comfort, function, and the freshest autumn looks, you’ll find an amazing assortment in our curated collection. Discover more options and get inspired for your next step by checking out Men's Autumn Shoes—your destination for all the must-have styles this season.

Top Picks For Fall Footwear For Men


FAQs

When picking out men’s fall shoes, look for materials like leather or water-resistant synthetics that can handle damp conditions. Traction is key for navigating slick sidewalks, and cushioned insoles help keep you comfortable during long days on your feet. Breathable linings are also great for those in-between days when the weather shifts from chilly to warm.

Absolutely! Men’s fall boots are designed to work with a variety of looks, from jeans and a hoodie for a laid-back vibe to chinos and a button-up for something a bit more polished. Their combination of rugged style and comfort makes them a staple that fits right in with both casual and semi-casual outfits.

To keep your fall footwear looking great, give them a quick wipe-down after wearing, especially if you’ve been out in the rain or mud. Use a soft brush or cloth for suede and a damp cloth for leather or synthetic materials. Let them air dry away from direct heat, and consider using a protective spray to guard against water and stains.

Men’s fall shoes make a thoughtful gift, especially as the season changes and everyone’s looking to update their wardrobe. They’re practical, stylish, and can be chosen to match the recipient’s personal style—making them a smart pick for birthdays, holidays, or just because.

This fall, earthy tones like brown, tan, olive, and deep burgundy are everywhere, along with classic black and grey. Chunky soles, mixed materials, and subtle details like contrast stitching are also trending. Look for boots, low-top sneakers, and slip-ons that blend comfort with fresh, on-trend style.