Would this Short Sleeve on up look alright under this Short Sleeve polo?

I'd wear it the other way (on up OVER polo) around if I were you. However, that's my personal taste. Go to the store, try it on and see what you think in the mirror. Bring a friend or a family member you trust to help you evaluate if it's a little silly or if it looks fine. Again, if you insist on wearing it the way you're saying, then do it! If you like it, what does it really matter if somebody else doesn't. Chick repellent? Yes, females are quite judgmental and harsh, but I don't think you should care if someone doesn't like what you're wearing as long as you are comfortable in it. You never know, somebody you least expect might think it's the cutest thing they've ever seen on you!! Good luck!!