It's something I've never tried, but plan to. One technique I've read explained has one paint the flesh tones, or under tones of underwear or whatever, first. Overcoat with thin, light coats of the final cover. You want more cloth paint coverage on areas where the cloth would not be touching the body beneath.
For heavily wrinkled/gathered/puckered cloth, apply flesh tones primarily in the valleys--where the cloth touches the body, leaving the peaks the cloth color.
Imagine a wet T-shirt contestant: not all the shirt is see through, only the parts most wet and most contacting the body.
A lot will depend on the degree of transparency you are after.
For heavily wrinkled/gathered/puckered cloth, apply flesh tones primarily in the valleys--where the cloth touches the body, leaving the peaks the cloth color.
Imagine a wet T-shirt contestant: not all the shirt is see through, only the parts most wet and most contacting the body.
A lot will depend on the degree of transparency you are after.