A charming "vintage" advertisement

[Tony Griffiths]

Pretty good - you are all on the right track. Mike and Bob were the closest - and Eric had the dress correct. Here's the original:

[Bob Culver]

Thanks Tony.
 
The runabout/raceabout is US style but unusually small.
 
I initially presumed military but too dandy for infantry. I vaguely thought UK air staff were later separated and may have had a different uniform, hence guessed date well into WW1.
 
If a US chauffeur there is probably a Pierce Arrow at home.
The artist clearly more familiar with fashion than aeroplanes.
The streaming wrap a liability in an open car. Who was the actress killed by her scarf?
 
I now understand the expression “boots and all”. The time he got them off would have forgotten why. He would need ankles as slender as the lady's.

In my deteriorated state if put them on in morning would have to sleep with feet on the mantlelpiece to get them off.

[David Stepney]

Bob,
The actress and dancer killed by her scarf in a freak motoring accident was Isadora Duncan. I believe the car was an Amilcar CGSS in which she was a passenger, when her long scarf caught in the rear wheel and broke her neck.

[Duncan Grimmond]

Have to admit I prefer the little yellow open-top...

[Tony Press]

A Mercer ?

[Bob Culver]

The car is in the general style of a Mercer but with a shortened bonnet. I have a 1918 catalogue of American makes. A Mercer a staggering $3600 whilst a Buick 6 $1265, Dodge 4 $890, Chev 4 $635 and a T less again. Little wonder the lady is well dressed.
Incidentally the Mercer was a  sv four, a 3 .75 x a mere 6.75 !!
There was a vast number of American makes, all very similar in specs and appearance.