Casual

Shop Simpson Outfitters for men’s casual footwear, offering a wide selection of stylish, comfortable, and versatile shoes for everyday wear. From loafers and sneakers to slip-ons and casual boots, our collection combines comfort, support, and laid-back style, perfect for any casual outing or relaxed day.

Men's Clogs
Men's Clogs
6 products
Men's Loafers
Men's Loafers
7 products
Men's Moccasins
Men's Moccasins
3 products
Men's Slip-Ons
Men's Slip-Ons
26 products
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  • OluKai Kākaha Mesh Lightweight Slip-On Shoe – Clay OluKai Kākaha Mesh Lightweight Slip-On Shoe – Clay
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    Olukai

    OluKai Kākaha Mesh Lightweight Slip-On Shoe

    Step into ultimate all-day comfort with the OluKai Kākaha Mesh Slip-On Shoe—now reimagined with a feather-light, breathable mesh upper for enhanced ventilation and flexibility. Featuring a removable and washable PU footbed, non-marking Wet...
    $99.99
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  • Crocs Classic Mossy Oak Bottomland Clog Crocs Classic Mossy Oak Bottomland Clog
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    Crocs

    Crocs Classic Mossy Oak Bottomland Clog

    Get ready for rugged style and all‑day comfort with the Crocs Classic Mossy Oak Bottomland Clog — now available at Simpson Outfitters. This iconic clog features Crocs’ signature Croslite foam construction for lightweight cushioning,...
    $64.99
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  • On Men's Cloudswift 4 - Alloy/Glacier On Men's Cloudswift 4 - Alloy/Glacier
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    On

    On Men's Cloudswift 4 Running Shoes

    On Men's Cloudswift 4 Take your running to the next level with On Cloudswift V4 Shoes. Crafted with a single-piece knit upper, these shoes offer a snug bootie construction that promotes maximum airflow. Further enhancing breathability is the perforated...
    $169.99
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  • Crocs Adult Classic Glitter Clogs - Black Crocs Adult Classic Glitter Clogs - Black
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    Crocs

    Crocs Adult Classic Glitter Clogs

    Crocs Adult Classic Glitter Clogs Incredibly light and fun to wear Ventilation ports add breathability and help shed water and debris Easy to clean and quick to dry Pivoting heel straps for a more secure fit Customizable with Jibbitz™...
    $40.00
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  • Florsheim Motor Moc Toe Venetian Driver - Cognac Florsheim Motor Moc Toe Venetian Driver - Cognac
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    Florsheim Shoe Company

    Florsheim Motor Moc Toe Venetian Driver

    Elevate your footwear collection with the Florsheim Motor Moc Toe Venetian Driver 13412-221, available at Simpson Outfitters. Crafted from premium cognac leather, these slip-on loafers offer a sophisticated look suitable for various occasions, from...
    $99.99
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  • Florsheim Norwalk Plain Toe Oxford - Congac Florsheim Norwalk Plain Toe Oxford - Congac
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    Florsheim Shoe Company

    Florsheim Norwalk Plain Toe Oxford - Congac

    Elevate your footwear collection with the Florsheim Norwalk Plain Toe Oxford 13369, available at Simpson Outfitters. These men's dress shoes feature a clean, classic upper complemented by a modern silhouette, making them suitable for both formal and...
    $144.99
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  • Florsheim Norwalk Plain Toe Oxford - Black Florsheim Norwalk Plain Toe Oxford - Black
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    Florsheim Shoe Company

    Florsheim Norwalk Plain Toe Oxford - Black

    Elevate your footwear collection with the Florsheim Norwalk Plain Toe Oxford 13369, available at Simpson Outfitters. These men's dress shoes feature a clean, classic upper complemented by a modern silhouette, making them suitable for both formal and...
    $134.99
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    Hari Mari Men's Fields Flip Flops - Bourbon Hari Mari Men's Fields Flip Flops - Bourbon
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    Hari Mari

    Hari Mari Men's Fields Flip Flops

    Hari Mari Men's Fields Flip Flops The classically comfortable Fields flip flops are perfect for day-to-day wear. These best-selling, tried-and-true sandals take you effortlessly from pier to patio, beach to bonfire. Fields men's sandals are durable,...
    Was: $65.00
    $48.75
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  • Crocs Men's Classic Realtree Max-7 Camo Clog Crocs Men's Classic Realtree Max-7 Camo Clog
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    Crocs

    Crocs Men's Classic Realtree Max-7 Camo Clog

    Experience the perfect blend of rugged style and unparalleled comfort with the Crocs Men's Classic Clog in Realtree MAX-7 Camo. Designed for outdoor enthusiasts, this clog features the authentic Realtree MAX-7 camouflage pattern, seamlessly...
    $64.99
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  • Hydrangea/Multi White/Black
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    Crocs

    Crocs Classic Marbled Clog

    Original. Versatile. Comfortable. The iconic clog that started a comfort revolution around the world is a do-it-all style that you’re sure to fall deeper in love with day after day. Our new marbled Croslite™ material creates a colorful effect...
    $40.00 - $54.99
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  • Skechers Slip-ins: Delson 3.0 - Roth Taupe Skechers Slip-ins: Delson 3.0 - Roth Taupe
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    Sketchers

    Skechers Slip-ins: Delson 3.0 - Roth Taupe

    Experience unparalleled comfort with the Skechers Slip-ins: Delson 3.0 - Roth sneakers. These shoes feature Skechers' exclusive Hands Free Slip-ins® technology, allowing for effortless, hands-free wear. The engineered knit and synthetic upper with...
    $79.99
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  • OluKai Men's Kākaha Nia Slip-On Shoe - Fox OluKai Men's Kākaha Nia Slip-On Shoe - Fox
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    Olukai

    OluKai Men's Kākaha Nia Slip-On Shoe

    ​The OluKai Men's Kākaha Nia Slip-On Shoe (Model 10557) seamlessly blends laid-back comfort with upscale style, making it a versatile addition to any wardrobe. Crafted from premium full-grain leather and soft suede, this loafer is designed for both...
    $129.99
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  • On Running Men's Cloud 6 Waterproof - Black/Black On Running Men's Cloud 6 Waterproof - Black/Black
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    On

    On Running Men's Cloud 6 Waterproof

    Conquer the elements with the On Running Cloud 6 Waterproof Men's Shoes, now available at Simpson Outfitters. Designed for the modern adventurer, these shoes feature a waterproof membrane to keep your feet dry during unexpected rain showers...
    $125.00 - $179.99
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