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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  • 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
  • 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...
    $139.99
  • sale
    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...
    Was: $89.99
    $62.99
  • 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
  • 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...
    $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
  • Skechers Slip-ins RF: Parson - Ralven Skechers Slip-ins RF: Parson - Ralven

    Skechers

    Skechers Slip-ins RF: Parson - Ralven

    Simply step in and go wearing Skechers Hands Free Slip-ins™ Relaxed Fit®: Parson - Ralven. Designed with our exclusive Heel Pillow™. This laceless style features a canvas upper with twin gore panels for ease of wear, a Skechers Air-Cooled...
    $74.99
  • sale
    Rocky Men's Dry-Strike SRX Outdoor Shoe - Brown Rocky Men's Dry-Strike SRX Outdoor Shoe - Brown

    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...
    Was: $109.99
    $82.49
  • Crocs Adult Unisex Classic Lined Clog - Black/Black Crocs Adult Unisex Classic Lined Clog - Black/Black

    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
  • Twisted X Men's Chukka Driving Moc Twisted X Men's Chukka Driving Moc

    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...
    $135.95