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Pilgrim 1911, Catalog page, socks.
Pilgrim 1928 Catalog page, men's underwear.
Pilgrim 1939 Catalog page, men's shirts.
Pilgrim 1949 Catalog page, neckties.
Pilgrim 1960, product publicity photo, hats.
The Pilgrim brand had a very long and successful life as a brand of Sears clothing for men, women and children. Pilgrim first appeared on men's socks in 1905, and, over the next six decades, it was extended to women's socks and stockings, men's shirts, ties, underwear, and children's clothing.

Sears' "satisfaction guaranteed" promises did not exist merely for the sake of appliances and Craftsman-brand tools. In the 1910s, Sears offered a three-month guarantee on packs of Pilgrimbrand Positive-Wear cotton socks. Pilgrim socks were popular items among Sears customers, and Sears added Pilgrim Babe socks for infants. By the 1920s, flannel shirts, undershirts, and union suits all bore the Pilgrim brand name.

The Pilgrim brand hit its high-water mark in the 1940s, when Sears sold Royal Ascot, Royalton, Tru-Point, and Nobility men's shirts all appeared in the Pilgrim line. Sears also sold Pilgrim undergarments for children, as well as Pilgrim-brand men's hats and pajamas.

In the early 1950s, Sears introduced permanent press men's dress shirts under Pilgrim brand name.

The fall/winter 1963-1964 catalog was the last edition to feature Pilgrim products, advertising Pilgrim-brand men's underwear.

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