Cool tie, cool hat, sharp lapels – what a dude. And such a beautiful sanguine face! I love his slightly raised eyebrows, almond eyes and half smile. I feel very warm towards him, as there is something in his expression that suggests kindness and charm.
The background in this booth photo is very unusual, so I would suggest it was added by the owners of a club or bar where the booth was situated. It is undated but I would guess, based on the quality of paper and the clothing style, it was taken sometime in the 1930s. There is self-adhesive album residue on the back (those albums date from the 1970s) which suggests it was loved and cared for for many years after it was taken.
The photo is of a slightly larger size than most of my booth photos. It measures 65 x 78 mm and came from the USA.