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You’ve got a favorite tee, a favorite button-down, favorite pair of jeans. But those boots are a little worn through the soles, sitting in the back of your closet. Time to complete your best casual look with a new favorite pair of boots. In this collection, find iconic chukka boots and more that are sure to give your look a stylish upgrade.

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  • Ecco Men’s Turn Chukka

    $230.0$119.0



  • Ben Sherman Men’s Aberdeen Boot

    $160.0$150.0



  • Ben Sherman Men’s Aberdeen Boot

    $160.0$53.0



  • Donald J Pliner Men’s Jasi Chukka

    $325.0$329.0



  • Original Penguin Men’s Birdie Lite Chukka

    $140.0$154.0



  • J. Artola Men’s Chuck Chukka

    $225.0$88.0



  • J. Artola Men’s Chuck Chukka

    $225.0$75.0



  • J. Artola Men’s Chuck Chukka

    $225.0$75.0



  • Tod’s Men’s Leather Boot

    $645.0$69.0



  • John Varvatos Men’s Star S Eva Chukka

    $228.0$



  • John Varvatos Men’s Star S Eva Chukka

    $228.0$



  • John Varvatos Men’s Star Strummer Winter Wingtip Boot

    $368.0$



  • John Varvatos Men’s Hipster Chukka

    $198.0$



  • Sebago Men’s Simsbury Laceup Boot

    $190.0$



  • Sebago Men’s Simsbury Chelsea Boot

    $190.0$



  • Sebago Men’s Metro Chelsea Boot

    $180.0$

: MEN