Men's Footwear

Shop Simpson Outfitters for men’s footwear, featuring a wide selection of stylish, durable, and comfortable shoes and boots for all occasions. From rugged outdoor boots and hiking shoes to casual sneakers and dress shoes, our collection is designed to provide maximum comfort, performance, and protection for your feet.

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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...
    $139.99
  • Olukai Men's Moloā Slipper - Toffee / Dark Wood Olukai Men's Moloā Slipper - Toffee / Dark Wood

    Olukai

    Olukai Men's Moloā Slipper

    Olukai Men's Moloā Slipper The Moloā Slipper is the purest form of relaxation. Made with premium nubuck leather, soft genuine shearling, and OluKai’s signature comfort, the Moloā will be your go-to slipper year-round. We use natural, high-character...
    $129.99
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    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
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    Reef Men's Leucadian - Brown Reef Men's Leucadian - Brown

    Reef Shoes

    Reef Men's Leucadian - Brown

    Reef Men's Leucadian - Brown A timeless silhouette designed with a premium suede upper and stitched details. With interior features like soft microfiber and our memory foam SWELLsole sockliner, the Leucadian is lightweight on the foot and supremely...
    Was: $99.99
    $69.99
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    Reef Men's Otis - Brown Reef Men's Otis - Brown

    Reef Shoes

    Reef Men's Otis - Brown

    Reef Men's Otis - Brown Recreating an icon. REEF takes on the Chelsea boot with the Otis. Designed with an smooth suede upper and our iconic SWELLsole sockliner, these mold to your foot for unbeatable comfort. Finished with front and back pull tabs and...
    Was: $99.99
    $69.99
  • On Men's Cloudrunner 2 - White/Sand On Men's Cloudrunner 2 - White/Sand

    On

    On Men's Cloudrunner 2

    On Men's Cloudrunner 2 Features a new mesh upper made from 100% recycled polyester Tongue loop to keep laces in place IN-SHOE COMFORT: Plush tongue for total comfort and easy step-in New Helion™ superfoam midsole for big energy...
    $149.99
  • New Balance Men's Fresh Foam X 1440 - White with Kelly Green and Gum New Balance Men's Fresh Foam X 1440 - White with Kelly Green and Gum

    New Balance

    New Balance Men's Fresh Foam X 1440

    New Balance Men's Fresh Foam X 1440 A versatile blend of premium comfort features and bold design details. Fresh Foam X midsole delivers our most cushioned Fresh Foam experience for incredible comfort TPU heel clip Wrapped rubber outsole for a bold...
    $89.99
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    XTRATUF Men's 6 inch Ankle Deck Boot Guy Harvey XTRATUF Men's 6 inch Ankle Deck Boot Guy Harvey

    XTRATUF

    XTRATUF Men's 6 inch Ankle Deck Boot Guy Harvey

    XTRATUF Men's 6 inch Ankle Deck Boot Guy Harvey The Ankle Deck Boot collection has been crafted specifically for off-shore anglers. Anglers are athletes, and like any athlete they demand the best footwear to help them perform at a high level. The Guy...
    Was: $119.99
    $89.99
  • Socksmith Shark Chums Cotton Crew Sock - Black
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    Socksmith

    Socksmith Shark Chums Cotton Crew Sock - Black

    Socksmith Shark Chums Cotton Crew Sock - Black Do you ever feel like your sock drawer is lacking a little bite?  L/XL 10-13 (Women's Shoe Size 10.5+ and Men's Shoe Size 9-13) 66% Cotton, 32% Nylon, 2% Spandex
    $9.99
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  • Carolina Boot Men's Flyweight CT SD Slip-On

    Carolina Boots

    Carolina Boot Men's Flyweight CT SD Slip-On

    Carolina Boot Men's Flyweight CT SD Slip-On Composite Safety Toe Mesh Lining Removable AG8 Intelli/Sphere Cement Construction Static Dissipative Rated PU Dual-Density Foam Comfort Footbed XL Extralight Industrial Plus Outsole Slip, Oil & Abrasion...
    $144.99
  • Wolverine Men's Carlsbad Waterproof 6" Work Boot - Brown Wolverine Men's Carlsbad Waterproof 6" Work Boot - Brown

    Wolverine

    Wolverine Men's Carlsbad Waterproof 6" Work Boot

    Wolverine Men's Carlsbad Waterproof 6" Work Boot With a classic style and all the comfort and durability you need to get the job done, the Carlsbad is a boot you can trust. Created with premium waterproof leather and enhanced cushioning in the midsole...
    $94.99