I would feel weird wearing stuff with "RF" on them. I am a college student and I don't want to be walking around with the RF logo on my clothes and have people think: WELL, there's a federer Fanboy...what a ******. It's the same reason I won't buy the no compromise blue bracelet even though i think it looks pretty good. Although the Live Strong bracelet wouldn't be weird cause it's meant to let others wear it; and it benefits medical research.
I think especially the RF hats, that would be weird. I much rather just wear the regular Nike swoosh.
I think you over estimate the amount of people who would know what the RF logo is. Besides, with all the stupid t-shirts going around these days, you can wear pretty much anything and it will only stick in someone's head for a split second before they move on to some other t-shirt with some crap on it.
I like the logo and think its pretty classic, but I've NEVER seen anyone wearing a shirt or hat with that logo on it. not att the courts, in the mall, on campuses, never. It's not like Nike runs ads with the logo plastered all over the place, i think you would probably get more questions about it than people thinking your Roger's #1 fan.
My mom bought me a bluegrass colored RF shirt last week; can't wait to wear it around, thanks moms!
(ps - i'm 30 yrs old)
-------UPDATE-------
Of course the first time I wore it, I was standing in line at Whole Foods and a lady walked by and commented on how much she liked the Federer shirt.