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Winnipeg Outfitters will resume shipping to all areas in Canada including PO Boxes. Thank you for your patience!
Winnipeg Outfitters will resume shipping to all areas in Canada including PO Boxes. Thank you for your patience!

Winter Sale 2025

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  • Women's Timberland Greyfield Sandal

    $95.00 - $95.00
    $95.00
    $95.00
    $95.00 - $95.00
    $95.00

    Take your warm weather style to new heights with the Greyfield strap sandals. This pair features premium Timberland leather, adjustable straps, an...

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    $95.00 - $95.00
    $95.00
    $95.00
    $95.00 - $95.00
    $95.00

  • Women's Timberland Stone Street 6-Inch Waterproof Boot

    $200.00 - $200.00
    $200.00
    $200.00
    $200.00 - $200.00
    $200.00

    Head for adventure with the bold, iconic look for this classic boot silhouette featuring a waterproof premium Timberland® leather upper, seam-seale...

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    $200.00 - $200.00
    $200.00
    $200.00
    $200.00 - $200.00
    $200.00
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    Women's Timberland Everleigh Chelsea Boot

    $190.00
    $190.00 - $190.00
    $190.00
    $133.00
    $133.00 - $133.00
    $133.00

    A durable and stylish addition to your wardrobe, these Everleigh Chelsea boots feature a pull-on style with dual stretch gore, an OrthoLite® footbe...

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    $190.00
    $190.00 - $190.00
    $190.00
    $133.00
    $133.00 - $133.00
    $133.00
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  • Women's Timberland Laurel Court Low Sneaker

    $95.00 - $95.00
    $95.00
    $95.00
    $95.00 - $95.00
    $95.00

    Comfortable, reliable sneakers are a necessity in everyone's shoe closet. These shoes feature an upper made with Premium Timberland leather and a R...

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    $95.00 - $95.00
    $95.00
    $95.00
    $95.00 - $95.00
    $95.00
  • Save 30% Save %

    Men's Timberland Lincoln Peak Lite Sandal

    $100.00
    $100.00 - $100.00
    $100.00
    $70.00
    $70.00 - $70.00
    $70.00

    Upper made with Premium Timberland®Leather and ReBOTL™ fabric. Convenient hook-and-loop closure. ReBOTL™ fabric lining. Compression-molded EVA mi...

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    $100.00
    $100.00 - $100.00
    $100.00
    $70.00
    $70.00 - $70.00
    $70.00
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  • Men's Timberland Mt. Maddsen Waterproof Mid Hiking Boot

    $150.00 - $150.00
    $150.00
    $150.00
    $150.00 - $150.00
    $150.00

    Experience rugged, trail-worthy performance with the Mt. Maddsen mid-hiker boot. The anti-fatigue comfort technology provides all-day comfort and s...

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    $150.00 - $150.00
    $150.00
    $150.00
    $150.00 - $150.00
    $150.00
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    Women's Timberland Newport Bay Oxford

    $60.00
    $60.00 - $60.00
    $60.00
    $30.00
    $30.00 - $30.00
    $30.00

    Canvas upper. EVA footbed. Rubber rand. Vulcanized construction. Rubber outsole.

    $60.00
    $60.00 - $60.00
    $60.00
    $30.00
    $30.00 - $30.00
    $30.00
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    Men's Timberland Lincoln Peak Slip On

    $110.00
    $110.00 - $110.00
    $110.00
    $55.00
    $55.00 - $55.00
    $55.00

    Upper made with waterproof Better Leather from an LWG Silver-rated tannery and ReBOTL™ fabric. Convenient slip-on style. ReBOTL™ fabric lining. C...

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    $110.00
    $110.00 - $110.00
    $110.00
    $55.00
    $55.00 - $55.00
    $55.00
    Save 50% Save %