I'd be a bit pissed off by seeing that in a window, too. Regardless of the painter's intentions, its spread-leg cowboy-booted presence on a shopping street is all of a piece with the parodic sexualisation and objectification of women's bodies on which drag/crossdressing thrives.
In a gallery or some other appropriate context it could perhaps be contextualised by the surrounding imagery etc to subvert its superficial message, but on a high street it is just more lads mag.
It's not as if it does anything much with the sexualised pose, it just replicates what is so often available as porn.