It was pretty cool to wear a t-shirt showing underneath your button down or polo back in high school.
If you must wear something underneath because you get chaffed nipples (hehehe) or sweat then wear a wife beater or v-neck.
Otherwise it's just not attractive.
Stylish and Ray Ban and/or Oakley in the same sentence? Never.
Check out some designer brands. Or you can go look at Spy Optic, Von Zipper (LOVE these), Smith Optic, etc.
I like my Dolces and Von Zippers.
I really don't care who I'm with. I'm not going to change me for anyone. However, depending on where we go will depend on how much 'rockstar' or 'dress' I go, or if I combine the two.