We may earn money from the companies mentioned in this products affiliate post.

Fact: It’s officially fall. You can’t keep wearing your favorite flip flops as much as you’d like summer to last all year. Why not swap them out for pair of shoes a bit more seasonally appropriate? These boots are just as comfortable as your dependable sandals, will keep your toes warm in cooler temperatures and are definitely stylish enough to pair with your favorite jeans or chinos. The best part? Each and every style is under $50. Guess the season change wasn’t so bad after all. The details: Brands include Generic Surplus, Nautica, Rockport and more.

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  • Nautica Men’s Vern Moc Toe Boot (Brown)

    $90.00$49.00



  • Nautica Men’s Andrew Lace-Up Boot (Tan NuBuck)

    $110.00$49.00



  • Nautica Men’s Thomas Boot (Black)

    $110.00$49.00



  • Nautica Men’s Thomas Boot (Brown)

    $110.00$49.00



  • JD Fisk Men’s Frederick Chukka (Brown)

    $149.00$49.00



  • Generic Surplus Men’s Work Boot (Black)

    $84.00$39.00



  • Generic Surplus Men’s Work Boot (Earth)

    $84.00$39.00



  • Generic Surplus Men’s Duck Canvas Boot (Dark Green/Earth)

    $125.00$49.00



  • Generic Surplus Men’s Duck Boot (Charcoal Grey)

    $130.00$49.00



  • Generic Surplus Men’s Duck Boot (Russet)

    $130.00$49.00



  • Generic Surplus Men’s Duck Boot (Black)

    $136.00$49.00



  • Unstitched Utilities Men’s Cargo Boot Mid Sneaker (Black)

    $130.00$26.00



  • Dr. Martens Men’s Walden Boot (Dark Brown)

    $140.00$49.00



  • Dr. Martens Men’s Walden Boot (Tan)

    $140.00$49.00



  • Tretorn Men’s Krona Mid Leather Chukka Sneaker (Sailing Grey)

    $100.00$39.00



  • Tretorn Men’s Walden Leather Boot (Black/Capers)

    $130.00$49.00



  • Cushe Men’s Surf Slip-On Chukka (Brown)

    $90.00$39.00



  • Timberland Abington Men’s Desert Boot (Light Brown)

    $165.00$69.00



  • Rockport Men’s Fairwood Ankle Boot (Black Scrunch)

    $125.00$49.00



  • Rockport Men’s Fairwood Ankle Boot (Dark Brown Scrunch)

    $125.00$49.00



  • Sebago Men’s Knight Boot (Luggage Tan)

    $160.00$49.00



  • Sebago Men’s Cumberland Lace-Up Boot (Waxy Red Brown)

    $165.00$49.00



  • Sebago Men’s Filson Beacon Chukka (Dark Brown/Wax Canvas)

    $165.00$79.00



  • Kenneth Cole REACTION Men’s Pro-Ceeding Boot (Black)

    $138.00$49.00

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