further thoughts
I am pretty sure the Pirates wore flannels in 1958 and moved to the vests in 1959. If accurate that would make 1959 the earliest possibility. I've confirmed the Pirates did appearances for Horne's department stores as early as 1958. Harmony Milk was a big sponsor/supporter of the Pirates. Most of the Harmony Milk player photos I've seen are autographed. The likelihood is they were from appearances. If you have the patience - you could try searching a newspaper archive of the Pittsburgh Press and Post Gazette looking for advertisements related to Harmony Milk sponsored appearances (That's what I did for Horne's a while ago). Based solely off the images my guess stands at 1959-1961 (thinking 1959-1960 more likely tied into the Jay photos).
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