A Legacy of Craftsmanship and Value

The Pioneer Series is the foundation of Why&Co—our first and defining collection, crafted to deliver the best balance of quality and value. Every element, from materials to construction, reflects our dedication to timeless craftsmanship and practical elegance, making each pair a worthy investment in both style and durability.

  • European-Sourced Uppers, Italian-Tanned

    Each pair begins with premium calf leather, carefully sourced from the finest tanneries in Europe. The leather undergoes an artisanal tanning process in Italy, enhancing its richness, durability, and ability to develop a beautiful patina over time.

  • Durable, High-Performance Outsoles

    Built for modern-day practicality, all Pioneer Series shoes feature high-density rubber outsoles from reputable manufacturers, ensuring flexibility, longevity, and superior grip—ideal for the urban gentleman navigating city life.

  • Traditional Blake-Stitch Construction

    Every shoe is crafted using Blake-stitch construction, an Italian shoemaking technique that enhances flexibility while maintaining durability. The result? A shoe that moves with you, offering comfort without compromising structure.

  • Our Own Lasts - Designed for everyone

    At Why&Co, we don’t just make shoes—we design them from the ground up. Instead of borrowing existing lasts, we meticulously develop our own, ensuring an exceptional fit tailored to the modern man’s needs. This dedication to R&D allows us to craft shoes that not only look elegant but also provide superior comfort and proportion.

The Pioneer Series represents more than just a collection—it’s our commitment to redefining Singaporean menswear footwear.

Every detail, from the silhouette to the finishing touches, stays true to our philosophy: quality without compromise.

The Pioneer Series

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  • Round Toe Captoe Oxford in Black, Wallich In Black Round Toe Captoe Oxford in Black, Wallich In Black

    Wallich In Black

    $279.00 SGD
    $279.00 SGD
  • Round toe wholecut oxford in black, Collyer in Black Round toe wholecut oxford in black, Collyer in Black

    Collyer in Black

    $279.00 SGD
    $279.00 SGD
  • Round Toe Captoe Oxford in Coffee, Wallich In Coffee Round Toe Captoe Oxford in Coffee, Wallich In Coffee

    Wallich in Coffee

    $279.00 SGD
    $279.00 SGD
  • Captoe oxford in black, george in black Captoe oxford in black, george in black

    George in Black

    $279.00 SGD
    $279.00 SGD
  • Apron stitch, split toe single monk strap in coffee, Mccallum in coffee Apron stitch, split toe single monk strap in coffee, Mccallum in coffee

    McCallum in Coffee

    $279.00 SGD
    $279.00 SGD
  • Quarter brogue oxford captoe in coffee, havelock in coffee Quarter brogue oxford captoe in coffee, havelock in coffee

    Havelock in Coffee

    $279.00 SGD
    $279.00 SGD
  • classic round toe penny loafer in coffee, duxton in coffee classic round toe penny loafer in coffee, duxton in coffee

    Duxton in Coffee

    $239.00 SGD
    $239.00 SGD
  • Captoe oxford in brown red, george in brown red Captoe oxford in brown red, george in brown red
    -$84.00 SGD

    George in Brown Red

    $195.00 SGD
    $279.00 SGD -$84.00 SGD $195.00 SGD
  • Wholecut double monkstrap in coffee, cross in coffee Wholecut double monkstrap in coffee, cross in coffee
    Sold out

    Cross in Coffee

    $195.00 SGD
    $279.00 SGD -$84.00 SGD $195.00 SGD
  • classic round toe penny loafer in black, duxton in black classic round toe penny loafer in black, duxton in black

    Duxton in Black

    $239.00 SGD
    $239.00 SGD
  • spilt toe, apron stitch derby in coffee, marina in coffee spilt toe, apron stitch derby in coffee, marina in coffee

    Marina in Coffee

    $279.00 SGD
    $279.00 SGD
  • Quarter brogue oxford captoe in black, havelock in black Quarter brogue oxford captoe in black, havelock in black

    Havelock in Black

    $279.00 SGD
    $279.00 SGD