Men's Size 9.5 Shoes

Step into comfort and quality with our collection of men's size 9.5 shoes, where every pair is crafted to support your adventures, big or small. Whether you're exploring the great outdoors or navigating city streets, our selection offers the perfect blend of durability and timeless style. From casual sneakers to rugged boots, each shoe is designed with versatility and lasting value in mind, ensuring you stay comfortable and confident wherever your journey takes you. At L.L.Bean, we believe that the right footwear can make all the difference, and our men's size 9.5 shoes are here to prove just that.

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Men's Stonington Shoes, Moc-Toes

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

Pros: Fit Quality Comfort Style Versatility
Men's Oboz Sawtooth X Hikers, Low

A ventilated, hazy gray trail shoe with nubuck leather upper and reliable traction for technical trails.

Pros: Great fit Attractive color Stylish Excellent support Beautifully designed
Men's Storm Chaser 5 Slip-Ons

A tough, waterproof slip-on with leather upper, rubber outsole, and exceptional cushioning for all-weather comfort.

Pros: High quality Warm and cozy Versatile design Easy to slip on Comfortable fit
Men's Handsewn Moccasins, Camp Moc

A classic brown moccasin with full-grain leather upper and rubber sole for excellent wet-surface traction.

Pros: Great fit High quality Durability Classic style Comfortable
Men's Bucksport Shoes, Plain Toe
Price was from: $170 now: $144

A rugged black leather shoe with Vibram® rubber outsoles and waterproof oiled-leather upper for all-day comfort.

Pros: Perfect fit Excellent quality Durable Great appearance 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 and comfort.

Pros: Lightweight Exceptional warmth Durable Comfortable from the start Good grip
Adults' New Balance 237 Running Shoes

A vintage-inspired running shoe with a suede, mesh, and nylon upper, offering comfort and a sporty look.

Pros: Retro look Softness Good fit Comfortable Trendy design
Men's Dirigo Sneakers, Slip-On
Price was from: $119 now: $54.99

A lightweight, ultra-soft slip-on sneaker with recycled polyester mesh and exceptional cushioning for all-day comfort.
Men's Eco Bay Sneakers, Leather

A pair of black full-grain leather sneakers with recycled rubber outsoles and anti-odor treatment for comfort.
Men's Allagash Handsewn Mocs, One-Eye

A durable slip-on moc with full-grain leather upper and lightweight rubber outsole for lasting comfort.
Men's Higgins Beach 4-Eye Slip-Ons, Print
Price was from: $79.95 now: $54.99

A lightweight, breathable canvas slip-on with a deep olive camo print and durable EVA outsole.
Adults' Blundstone 500 Chelsea Boots

A pair of premium black leather pull-on boots with shock-absorbing construction and cushioned comfort.
Men's Bean Boots, Rubber Mocs

A Maine-made slip-on boot with waterproof rubber bottom, supple leather upper, and durable chain-tread outsole.
Men's Bean Boots, Gumshoes

A Maine-made, weather-ready gumshoe with durable leather/rubber construction, triple-needle stitching, and enhanced comfort.
Men's Downeast Slip-Ons, Wool

A cozy, cocoa-colored slip-on with a wool blend upper, cushioned EVA footbed, and durable rubber outsole.
Men's Katahdin 2 Sneakers, Suede
Price was from: $109 now: $74.99

A lightweight trail shoe with a durable suede upper, VertiGrip rubber outsole, and all-day comfort.
Men's On Cloudmonster 2 Running Shoes

A highly cushioned, responsive road runner with recycled polyester upper and dual-density Helion™ superfoam.
Adults' Blundstone 550 Chelsea Boots

A rustic brown leather pull-on boot with superior shock absorption and cushioned comfort for all-day wear.
Men's Brooks Adrenaline GTS 24 Running Shoes

A black running shoe offering cushioned support and breathable comfort with nitrogen-infused midsole foam.
Men's New Balance 480 Court Shoes

A gray leather and rubber court shoe featuring breathable mesh, classic color-blocking, and a durable outsole.
Men's Urban Storm Shoes, Waterproof Insulated

A rugged, waterproof, and insulated shoe in dark cement, made from leather, rubber, and plastic.
Men's Oboz Sawtooth X B-DRY Hikers, Low

A rugged brown trail shoe with waterproof leather, breathable lining, and multi-directional lugs for superior traction.
Men's HOKA Transport Shoes

A sustainable blue athleisure shoe with recycled materials and water-resistant features for active comfort.
Men's Elevation H2O Shoes

A lightweight green water-friendly shoe with a breathable nylon/neoprene upper and cushioned EVA midsole.

Men's Size 9.5 Shoes

When it comes to men’s size 9.5 shoes, the right pair has a way of making every step outside feel just a little more comfortable, whether you’re heading out for a hike, tackling yardwork, or simply taking the dog for a walk around the block. This size is one of the most popular for men, making it a breeze to find a wide range of styles and designs to suit just about any activity or personal taste. From sturdy trail shoes built to handle rocky paths and muddy fields, to easygoing slip-ons perfect for a backyard barbecue, there’s a pair for every part of your day. For those who spend a lot of time on their feet, look for features like supportive insoles, breathable uppers, and outsoles designed to grip everything from wet grass to city sidewalks. The best shoes in this size are made to last, crafted from quality materials that hold up to repeated wear and offer reliable comfort from the first step to the last. Many men find themselves reaching for the same trusted pair day after day, whether it’s to run errands or explore the local rail trail, and with good reason: shoes that fit well and feel great quickly become everyday essentials.

June brings long days and plenty of opportunities to get outside, making now a great time to refresh your footwear or pick up a thoughtful gift for someone special. A new pair of men’s size 9.5 shoes can be just the thing for a recent graduate heading off to a summer job, a dad who enjoys weekend camping trips, or anyone who appreciates the simple pleasure of a walk in the park. Consider what the recipient enjoys most—maybe it’s casting a line at the lake, playing catch in the yard, or relaxing on the deck after a day’s work. Shoes designed for the outdoors often come with extra durability and comfort features, like cushioned midsoles and rugged outsoles, so they’re ready for whatever summer brings. For those who appreciate versatility, look for options that transition smoothly from trail to town, pairing well with jeans, shorts, or even casual slacks. It’s also worth considering shoes that are easy to clean and quick to dry, especially if you’re planning on spending time near the water or in the garden. With the right pair, you’ll be prepared for spontaneous adventures, whether that means a last-minute road trip or an impromptu game of frisbee at the park.

Finding the perfect fit is key, and sometimes it’s helpful to compare different sizes to see what feels best, especially if you’re shopping for someone else or if your foot size is in between. If you’re curious about how a slightly larger size might work for you—perhaps to accommodate thicker socks or provide a bit more room on longer walks—take a look at our selection of Men's Size 10.5 Shoes for even more options. No matter which size you choose, quality and comfort are always at the forefront, ensuring each pair is ready for everyday adventures, big and small. With so many possibilities, you’re sure to find a pair that feels just right, letting you make the most of every sunny day and star-filled night this season.

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Men's Size 9.5 Shoes