You are nice to weigh in as a Prudie. The young man will probably have to be a little more explicit than just mentioning the Great Kate's name, however, because her style of dressing is most associated with slax and turtlenecks. Also, the wonderful Ms. Hepburn was never known for remarkable gazongas. Prudie guesses it's the Hepburn aura you're going for, since, unlike you, there was no Marilyn Monroe body underneath all those tailored clothes. Just as an aside, Prudie cannot quite understand your wearing the "T-shirt bra" with its thin padding. Wouldn't padding--even thin--be gilding the lilies?
Three little addenda to your advice to Junior Exec.
1) If he wishes to continue to advance his career, he might want to refer to his well-endowed partner as a "woman," not a "girl." If, however, she is under 18, then he has a completely different problem.
2) He might want to establish the difference between "plain" and "major pair of hooters." The opposite of "plain" is actually "beautiful," and the opposite of "major hooters" is "flat as a pancake."
3) What exactly is the problem he wants advice for? Is he actually suggesting that having a bazoomba fetish might hamper his career? Wake up and smell the coffee, Junior. This is America!
Nitpicker, Emmaus, PA.