Men's Size 8.5 Shoes

Finding the right fit is essential, and our collection of men's size 8.5 shoes is here to ensure every step you take is as comfortable as it is stylish. With a variety of styles crafted for both everyday wear and outdoor adventures, these shoes offer the perfect blend of quality and durability. Whether you're exploring city streets or hiking your favorite trail, you'll appreciate the lasting value and timeless appeal that each pair brings to your wardrobe. Embrace the great outdoors with confidence, knowing that your footwear is designed to support your active lifestyle in comfort and style.

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Men's Wicked Good Moccasins

A pair of men's brown suede moccasin slippers with shearling lining and durable rubber outsole.

Pros: High quality Warmth Durable Comfortable Good fit
Men's Stonington Shoes, Moc-Toes

A rugged dark cocoa leather shoe with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.

Pros: Fit Quality Comfort Style Versatility
Men's Stonington Boots, Moc-Toe

A rugged dark oakwood leather boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.

Pros: Durable construction Versatile use Lightweight design Stylish appearance Comfortable fit
Men's Bucksport Shoes, Plain Toe

A rugged, waterproof brown leather shoe with Vibram® rubber outsoles and anti-odor technology for all-day comfort.

Pros: Perfect fit Quality Durability Excellent value Comfortable
Men's Snow Sneaker 5 Boots, Lace-Up

A lace-up winter boot with suede leather, rubber, and 200g ColdShield insulation for exceptional warmth.

Pros: Lightweight Exceptional warmth Durable Good grip Comfortable
Men's Stonington Oxford Shoes, Plain Toe

A rugged, deepest brown leather shoe with sneaker-like comfort, water-resistant protection, and a molded rubber outsole.

Pros: Good looking Rain resistance Comfort True to size Non-slip soles
Men's Bean's Comfort Fitness Walking Shoes

A weatherproof, cushioned walking shoe with a breathable polyester mesh upper and durable VertiGrip rubber outsole.

Pros: Fit Quality Comfort Durability Arch support
Men's Snow Sneaker 5 Shoes, Lace-Up

A versatile winter sneaker with suede leather, rubber, ColdShield insulation, and a waterproof membrane for snowy conditions.

Pros: Great fit Good traction Comfortable Keeps feet dry Excellent warmth
Men's Bean Boots, 6.5" Chelsea

A waterproof Chelsea boot with a soft leather upper and durable rubber bottom, perfect for wet conditions.
Men's Elevation Hiking Shoes, Ventilated
Price was from: $130 now: $109

A lightweight gray mesh and rubber hiking shoe with ventilated, seamless comfort and grippy traction.

Pros: Comfortable for walking and hiking Attractive style Lightweight design Perfect fit for narrow feet Quality construction materials
Men's Elevation Hiking Shoes, Waterproof
Price was from: $150 now: $124

A lightweight, waterproof hiking shoe with recycled polyester upper and durable rubber outsole for reliable traction.

Pros: Acceptable color Waterproof protection Comfortable fit
Men's Keen Targhee IV Waterproof Hiking Shoes

A waterproof leather hiking shoe offering stability, support, and comfort with eco-friendly features and durable traction.
Men's Bean Boots, Slip-On Rubber Mocs

A weather-ready slip-on moc with durable leather upper and waterproof rubber bottom, ideal for wet conditions.
Men's Elevation H2O Shoes

A lightweight green water-friendly shoe with breathable nylon/neoprene, cushioned EVA midsole, and VertiGrip outsole.
Men's New Balance 574V3 Walking Shoes

A versatile walking shoe with breathable suede-and-mesh upper and durable rubber outsole for all-day comfort.
Men's New Balance 990V6 Running Shoes

A blue leather and rubber sneaker featuring breathable mesh, plush cushioning, and reliable all-day stability.
Men's Bean Boots, Rubber Mocs

A brown leather and rubber slip-on moc with waterproof protection, enhanced comfort, and durable triple-needle stitching.
Men's Bean Boots, 8"

A Maine-made, weather-ready boot with a durable leather upper and long-lasting rubber outsole.
Men's Portland Boots, Lace-Up
Price was from: $200 now: $169

A heritage-inspired black leather boot with a Vibram® rubber outsole, perfect for city exploration.
Men's HOKA Bondi 9 Running Shoes

A black running shoe with ultra-cushioned EVA foam midsole and 55% recycled polyester mesh upper.
Men's Kennebec Oxford Shoes

A versatile dark earth leather oxford with athletic comfort, anti-odor footbed, and reliable VertiGrip traction.

Pros: Great fit Versatile color Stylish design Comfortable wear Dressy look

Men's Size 8.5 Shoes

Finding the right pair of men’s size 8.5 shoes can make all the difference when you’re heading outside for an afternoon hike, a stroll through town, or just tackling the everyday. The perfect fit isn’t just about comfort—it’s about supporting every step, whether you’re lacing up for a day on the trails or slipping on shoes before a backyard cookout. This time of year, as summer winds down and the first hints of cooler weather start to roll in, having shoes that can handle a little bit of everything is key. Many folks look for shoes that offer a blend of durability and versatility, built to keep up with changing plans and weather. Breathable materials and supportive soles are especially appreciated in August, when warm days can quickly turn into cool evenings. For anyone who spends time outdoors—whether it’s for a quick walk after work, a camping trip with friends, or a weekend spent exploring local parks—having reliable shoes in the right size means you’re always ready to go, with no need to slow down or sit out.

Men’s size 8.5 shoes are a thoughtful gift for anyone who values comfort and practicality, from recent graduates starting a new job to dads who spend weekends coaching little league or grilling in the backyard. They’re also a great choice for those who appreciate timeless style and long-lasting value in their gear. When choosing shoes, it’s a good idea to consider how and where they’ll be worn. Some prefer slip-on styles for convenience, while others opt for lace-up designs for extra support during longer outings. Features like cushioned insoles, sturdy outsoles, and easy-to-clean materials are all worth seeking out, especially if you’re shopping for someone who’s always on the move. And if you ever find yourself between sizes, or shopping for a growing teen, it helps to know that a full range of sizes is available—including options like Men's Size 9 Shoes—so you can always find the best fit. With the right pair, every adventure feels just a little bit easier, and every day a little more comfortable.

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Men's Size 8.5 Shoes