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
5 products
Men's Loafers
Men's Loafers
6 products
Men's Moccasins
Men's Moccasins
3 products
Men's Slip-Ons
Men's Slip-Ons
24 products
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  • Rocky Men's Dry-Strike SRX Outdoor Shoe - Brown Rocky Men's Dry-Strike SRX Outdoor Shoe - Brown
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    Rocky Shoes & Boots

    Rocky Men's Dry-Strike SRX Outdoor Shoe

    Rocky Men's Dry-Strike SRX Outdoor Shoe We have expanded our original Dry-Strike collection into the Dry-Strike SRX. This 3" twin gore slip-on shoe is built with full grain leather on our non-marking oil- & slip-resisting Dry-Strike outsole perfect...
    $109.99
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  • Crocs Adult Unisex Classic Lined Clog - Black/Black Crocs Adult Unisex Classic Lined Clog - Black/Black
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    Crocs

    Crocs Adult Unisex Classic Lined Clog

    Crocs Adult Unisex Classic Lined Clog 100% Synthetic Imported Ethylene Vinyl Acetate sole WARM AND FUZZY FEELINGS INSIDE: Designed with function and warmth in mind, the soft and lined Crocs for men and women are great as a slipper but also perfect for...
    $59.99
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  • Twisted X Men's Chukka Driving Moc Twisted X Men's Chukka Driving Moc
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    Twisted X

    Twisted X Men's Chukka Driving Moc

    Twisted X Men's Chukka Driving Moc The men's casual chukka driving moc is a true Twisted X® original! Handcrafted in full-grain leather, the chukka driving moc makes an unforgettable statement about true comfort and style in casual footwear. Blending...
    $149.95
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  • OluKai Men's Nohea Mesh - Mustang/Lime Peel OluKai Men's Nohea Mesh - Mustang/Lime Peel
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    Olukai

    OluKai Men's Nohea Mesh - Mustang/Lime Peel

    OluKai Men's Nohea Mesh - Mustang/Lime Peel The Nohea Mesh brings together old school style and modern construction to bring you a new level of comfort and style. Part of the OluKai Mauka Collection, the Nohea has a lightweight and breathable air mesh...
    $99.99
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  • Clarks Men's Shacre Boot-Beeswax Leather Clarks Men's Shacre Boot-Beeswax Leather
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    Clarks

    Clarks Men's Shacre Boot

    Clarks Men's Shacre Boot These ankle boots have a lace closure and work well with jeans or chinos. The beeswax leather upper feels as contemporary and uncluttered as ever, while underfoot you can feel the benefit of a Rock rubber outsole for grip and...
    $94.99
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  • OOFOS Men's OOahh Slide Sandal - Black OOFOS Men's OOahh Slide Sandal - Mist
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    OOFOS

    OOFOS Men's OOahh Slide Sandal Black

    An evolution of the OOriginal, featuring an agile OOfoam™ strap for additional support and comfort. OOfoam™ technology absorbs 37% more impact than traditional footwear. Proprietary footbed design reduces stress on knees, ankles and other...
    $59.95
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  • OOFOS Original Sandal-Mauve OOFOS Original Sandal-Navy
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    OOFOS

    OOFOS Original Sandal

    OOFOS Original Sandal The OOFOS story begins with the OOriginal Sandal. This combination of sleek design and revolutionary OOfoam™ recovery technology lays the groundwork for all future styles and models.
    $59.95
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  • Olukai Moloa - Ray/Toffee Olukai Moloa - Ray/Toffee
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    Olukai

    Olukai Moloa - Ray/Toffee

    Moloa might translate to “lazy,” but we like to think “laidback” is a better fit. From the boardwalk to the boardroom, the dapper Moloa in antiqued and waxed nubuck leather can handle a serious meeting or a spontaneous night out...
    $139.99
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  • Georgia Boot Cedar Falls Moc-Toe Slip On Georgia Boot Cedar Falls Moc-Toe Slip On
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    Georgia Boots

    Georgia Boot Men's Cedar Falls Moc-Toe Slip On

    Georgia Cedar Falls Moc-Toe Slip-On Shoes feature full grain leather construction, a moisture management lining, and double elastic gore on slip on’s. Technologies: Moisture-wicking lining Full-grain leather AMP (Advanced Memory Polyurethane)...
    $99.99
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