I would buy the tank and a nice shirt or two, and enjoy some nice evenings out with someone special.

It sounds like the issue you are dealing with is the investment, and not the social connotations: Will it be worth it? That's a question a lot of us have asked at some point. I don't know anyone here who'd say they made a bad decision.

As for the other debate, since the objection I think most men have about women wearing menswear is the feminization of their things, I'm willing to bet that's not your style and no one is going to accuse you of that.

But you will look like a million bucks!
(or quid, or whatever)

Regards,
Rex.