Drew. I have pics of my wife's uncles( UK late 30's) with similar hairstyle to the man holding the baby. His specs and double breasted jacket and hairstyle give him a Glen Millar look. So maybe 1940's
I am thinking also of the young librarian in "China Town"of Jack Nicholson/ Fay Dunaway fame which I think was set in the late 30's/early 40s.
As a baby I looked similar to this baby in clothes style.I was born '46 and as baby clothes in '46 probably changed little from a few years before, it all points to late 30's/early 40's
I feel we can rule out the 1920s or even early 30's. The older gent has what appears to be a very broad but short tie which is gaudily painted. This should help date it as well. It ressembles what we in the U.K. later referred to as a Spiv's tie. Popular with musical hall type comedians like Max Millar and Tommy Trinder and the "Spiv" reference was to black marketeers during rationing during WWII. The style of tie persisted through the 40's.
All in all, I think it strongly points to the late 30s/ early 40's but more likely the early 40s. I know my references are to the U.K but the two countries mirrored each other to a large extent.
Let us know what transpires. I like these kind of puzzles