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Top Men's Shoes Deals from your favorite stores for October 2025

The biggest price drops from Men's Shoes over the past 30 days.

    Allen Edmonds logo

    Allen Edmonds Winstonmok Wingtip Derby Dress Shoe ...

    Discover the Allen Edmonds Winstonmok Wingtip Derby in Navy Suede, a shoe that masterfully blends heritage craftsmanship with contemporary style. This size 14.0 3E option ensures a generous fit without compromising on elegance, making it a go-to choice for those who value both comfort and sophistication. Handcrafted in our Port Washington workshop, each pair is built to last a lifetime. The 360-degree bench welt construction provides exceptional durability and stability, while the premium navy suede upper offers a rich texture that stands out in any setting. Intricate brogue detailing and contrast stitching highlight the shoe’s refined lines, giving it a distinctive character that commands attention. Built on our renowned 65 last, the Winstonmok delivers a classic fit that feels as good as it looks. Inside, the leather-lined interior and CustomCork footbed mold to the shape of your foot over time, offering personalized support with every step. The durable Dainite rubber sole not only ensures long-lasting wear but also provides reliable traction without picking up dirt, making these shoes suitable for both office and casual outings. Whether you’re dressing for a formal event or elevating your everyday style, the Winstonmok Wingtip Derby offers unmatched versatility. Available now at AllenEdmonds.com, this shoe is more than an accessory—it’s an investment in timeless American craftsmanship. Plus, with our expert recrafting service, you can enjoy your Allen Edmonds for years to come. Step into confidence and style with a shoe designed for those who appreciate the finer details.
    $450.00
    $329.0027% OFF
    Ponto Footwear logo

    The Pacific Women's - Oak / 6.5

    All Pacific sales are final. No returns or exchanges are permitted. The Pacific is made to look like work, and feel like play. As comfortable as a cloud, light as a feather, and shockingly sustainable, the Pacific is your do everything, go anywhere shoe. To Inspire Resilience in People and Planet ™
    $148.00
    $74.0050% OFF