The last pic "ultra modern Boeing" is a Boeing 247. It has an interesting combination of features, for it has the reverse-sloping windshield that only the first aircraft of this type had (the mainstream 247D production ones had conventional slope) but it has three-blade constant speed propellers, where the first had two-blade fixed props.
The bulk of the 247s were built for the initial incarnation of United Airlines, which together with Boeing and Pratt & Whitney were all owned by the forebears of the current United Technologies. It does look like it's in the early United colour scheme of the times (later they put an art-deco blue/white scheme on their 247s).
My guess is that it is posed for publicity when the type was new and the latest thing at the 1933 Worlds Fair in Chicago, and that Clara Livingston was known for some prior aviation achievement rather then being the aircraft's pilot. The overweight gentleman who has bought a suit two sizes too small for himself looks vaguely familiar from other historic photos, like some Boeing/United bigwig. Anyone like to fill in more ?