This photo was posted to Flickr quite a while ago, but I just realized I never posted it here.
Seated is Mary’s grandfather, Giovani “John” Maltese, on her mother’s side. The photo was likely taken in Wheeling, W.Va. Man standing is also unknown. This was printed on a postcard.
The date is unknown, but someone over on the Flickr page has a good guess:
The calf skin, hard cap toed shoes and ankle laces plus the “barbershoppe” stripe shirt and bow tie place the time square in the mid ’20s. These two were rather “dapper” at that. Very well dressed for the time. Pre-depression.
You can find a few more historic photos in our Flickr account’s Our Heritage set.