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.

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  • Reef Cushion Phantom 2.0 Brown/Tan Men's Sandals Reef Cushion Phantom 2.0 Brown/Tan Men's Sandals

    Reef Shoes

    Reef Terramar Grey/Tan Men's Sneakers

    The Reef Terramar Grey/Tan Sneakers seamlessly blend style and comfort. Designed with a lightweight, breathable stretch-knit upper complemented by rich suede accents, these sneakers ensure your feet stay cool and comfortable throughout the day. The...
    $74.99
  • Reef Ojai Classic Dark Brown Sandals Reef Ojai Classic Dark Brown Sandals

    Reef Shoes

    Reef Ojai Classic Dark Brown Sandals

    Experience unparalleled comfort and timeless style with the Reef Ojai Classic Dark Brown Sandals. Crafted with a premium suede upper and lined with buttery soft glove leather, these sandals offer a stitchless and seamless interior for all-day wearability...
    $84.99
  • Reef Ojai Classic Dark Brown Men's Sandals Reef Ojai Classic Dark Brown Men's Sandals

    Reef Shoes

    Reef Cushion Norte Tan Men's Sandals

    Experience exceptional comfort and timeless design with the Reef Cushion Norte Tan Sandals. Crafted with innovative nitrogen-infused EVA foam, these sandals offer a lightweight, water-friendly cushioning that your feet will appreciate. The overlasted...
    $79.99
  • Reef Men's The Raglan - Fossil/Grey Reef Men's The Raglan - Fossil/Grey

    Reef Shoes

    Reef Men's The Raglan - Fossil/Grey

    The Raglan Fossil/Grey Flip Flops Step into superior comfort with The Raglan Fossil/Grey, a casual flip flop designed for the modern man. This water-friendly footwear features an overlasted strap paired with a soft padded lining, ensuring a comfortable...
    $54.99
  • New Balance 515 V3 Men's Sneaker - Slate Grey New Balance 515 V3 Men's Sneaker - Slate Grey

    New Balance

    New Balance 515 V3 Men's Sneaker

    The New Balance 515 V3 Men's Sneaker is a modern classic designed for everyday wear, combining comfort, durability, and heritage-inspired style.​ Key Features: Suede and Mesh Upper: The upper combines suede and mesh materials, providing a balance...
    $64.99 - $74.99
  • Crocs Classic Denim Clogs - Moonlight Crocs Classic Denim Clogs - Moonlight

    Crocs

    Crocs Classic Denim Clogs

    Crocs Classic Denim Clogs Bring blue jean style to your footwear with the Crocs Classic Denim Clog. These womens clog sandals feature a denim graphic print, complete with stitching and a jeans-inspired rivet on the strap, for a fun look. With the...
    $54.99
  • Crocs Men's Realtree APX Classic Clog - Multi Crocs Men's Realtree APX Classic Clog - Multi

    Crocs

    Crocs Men's Realtree APX Classic Clog

    Crocs Men's Realtree APX Classic Clog Strikingly real camo meets iconic comfort. The Realtree APX Classic Clog gives you the rugged style of a Realtree camouflage print with the comfort of Crocs. Using new approaches to depth, color and texture, the APX...
    $59.99
  • Birkenstock Boston Suede Leather - Taupe Birkenstock Boston Suede Leather - Taupe

    Birkenstock

    Birkenstock Boston Suede Leather - Taupe

    Birkenstock Boston Suede Leather - Taupe Our most sought-after clog, the Boston lends a fashion-forward edge to any style. Velvety suede gives the laid-back look classic, every season appeal. Featuring an additional foam layer for cushioning, the soft...
    $159.99
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    Olukai Lae‘ahi Lī ‘Ili - Dark Java Olukai Lae‘ahi Lī ‘Ili - Dark Java

    Olukai

    Olukai Lae‘ahi Lī ‘Ili

    Olukai Lae‘ahi Lī ‘Ili Made from premium full-grain waterproof leather, the Lae‘ahi Lī ‘Ili offers a blend of style and versatility with its natural color palette. The shoe is decorated with intricate debossed Hawaiian kapa...
    Was: $139.99
    $104.99
  • Reef Men's Terramar Le - Tan Reef Men's Terramar Le - Tan

    Reef Shoes

    Reef Men's Terramar Le - Tan

    Reef Men's Terramar Le - Tan The Terramar Leather is a premium version of a classic sneaker that can be dressed up or styled casually. The upper features unlined leather for an ultra-soft and flexible feel while a cushy EVA outsole provides all-day...
    $89.99
  • Under Armour Men's US SL Franchise Wide - Black/White Men''S Us Sl Franchise Wide

    Under Armour

    Under Armour Men's US SL Franchise Wide

    MEN'S US SL FRANCHISE WIDE Football Cleats Experience unbeatable durability and structure with the MEN'S US SL FRANCHISE WIDE Football Cleats, featuring a robust 3D printed upper. These cleats are designed to withstand the most intense football games,...
    $49.99
  • Merrell Men's Moab Adventure 3 Moc - Earth Merrell Men's Moab Adventure 3 Moc - Earth

    Merrell Footwear

    Merrell Men's Moab Adventure 3 Moc - Earth

    Merrell Men's Moab Adventure 3 Moc - Earth   Get all-day comfort with the same out-of-the-box fit you expect from Moab. The Moab Adventure 3 Moc delivers a lifestyle look along with technical features such as a Vibram® TC5+ outsole. •...
    $109.95
  • sale
    Skechers Men's Sport Squad Chaos - Grey Skechers Men's Sport Squad Chaos - Grey

    Skechers

    Skechers Men's Sport Squad Chaos - Grey

    Skechers Men's Sport Squad Chaos - Grey Step into athletic style and comfort wearing Skechers Hands Free Slip-ins®: BOBS Sport™ Squad Chaos - Tough Walk. Designed with our Exclusive Heel Pillow™, this fashion style features a mesh and...
    Was: $64.99
    $48.74
  • Reef Men's Water Coast Shoes - Grey Reef Men's Water Coast Shoes - Grey

    Reef Shoes

    Reef Men's Water Coast Shoes

    Reef Men's Water Coast Shoes Our new Water Coast is ready for all your water-happy activities, from beach walks to boat rides. This everywhere shoe includes the same ridiculously soft, bouncy comfort as our famous Cushion Coast, but along with its EVA...
    $64.99
  • Skechers Men's Slip-Ins Slade-Ocon - Taupe Skechers Men's Slip-Ins Slade-Ocon - Taupe

    Skechers

    Skechers Men's Slip-Ins Slade-Ocon

    Skechers Men's Slip-Ins Slade-Ocon Elevate your everyday style with the Skechers Slip-Ins Slade-Ocon Men’s Casual Shoe! This sharp-looking slip-on style features a breathable mesh upper and memory foam insole for relaxing strides. The lightweight...
    $74.99
  • Skechers Men's Slip-ins Delson 3.0 - Roth - Taupe Skechers Men's Slip-ins Delson 3.0 - Roth - Taupe

    Skechers

    Skechers Men's Slip-ins Delson 3.0 - Roth

    Skechers Men's Slip-ins Delson 3.0 - Roth - Taupe Simply step in and go wearing Skechers Hands Free Slip-ins®: Delson 3.0 - Roth. Designed with our exclusive Heel Pillow™. This Classic Fit style features an engineered knit and synthetic upper...
    $74.99