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maia comments on Rationality witticisms suitable for t-shirts or bumper stickers - Less Wrong Discussion
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I think this depends very much on your social circle and social goals. Wearing clothing with slogans on it is a high variance strategy: high attractiveness to a few people, low or even negative attractiveness to others. Wearing slogan-less clothing is more low variance; probably no one will object, but likely none of your responses will be as positive as the maximum positive response from wearing a T-shirt with a slogan on it. Both strategies can be useful, depending on what you are trying to accomplish.
Personally, I wear shirts with nerdy slogans on them, and anecdotally have had several positive interactions with people who came up to me to say "I like your shirt." (And I doubt I've lost much by turning people off.)
Also, I'm unconvinced that, in a casual context, wearing a shirt with a slogan on it is as negative as you suggest. I see people wearing shirts with slogans I don't get all the time, and I think I just ignore them, or occasionally ask what they mean (which rarely gets me very far conversation-wise, but doesn't cause me to dislike the person).
On the other hand, if you're trying to project an aura of Serious Grownup, it's probably a bad idea.
EDIT: Unless you're talking about shirts with controversial slogans, I suppose. That's even more high-variance, but again, in some contexts could still be a good idea. (I was thinking of things like "Engineering: It's like math, but louder.")
Shirts I've gotten comments on that I took as positive:
But I'm also quite certain that context matters. Family, polite old ladies, nerds (of varying extremes), and Chinese people tend to be the majority of people I interacted with once I got to eighth grade and my anti-idiot filters successfully limited my interactions with anyone else. (Nowadays it's just family, but I've gone into that elsewhere.) I'm sure an "Of course I care! That's why I'm calculating probabilities!" would get (mostly neutral or positive) reactions, but how that translates into real world applications I can only imagine (I physically cannot read body language and a non-negligible number of people might be artificially polite to me because of my eyes).
Depends what you're wearing instead. T-shirts with cute slogans on them are nowhere near the only way to make an impression with your clothes; in fact, I'd consider them a pretty cheap and lazy way to send a message as such things go.
You're probably right if I'm to take a plain T-shirt and Levi 501s as the implied alternative, though.
True. This works for attractiveness as well. Generally stylish clothes will give you low variance, while dressing to please a specific crowd (goths, emo rockers, etc.) will give you high variance.