Heh, coincidentially, I have written about this in my first and to date only blog post here.
Basically, keep it simple. I have included advice on what I'd put on a shirt in the comments. For your convenience, here they are, copypasted. After being asked by @G-Man about what I'd put on the shirts, I said this:
It's probably easier if we go the other way around. What to not put on a shirt.
- Funny captions or a witty statement: Who hasn't looked at a person with an "I'm with stupid"-shirt and rolled his eyes? And if it's an insider joke from this site, nobody will get it, since the world is rather big compared to this site.
- Faces. A drawing that is a two-dimensional represenation of a three dimensional thing that we see every day and assoicate a specific form with is a bad idea because we do react strongly when that thing with all its associations and fixed points of references is distorted. And no matter how good a face might look on a drawing board, you will not be able to make it look good on a T-Shirt. Because everyone who sees it will react negatively before they go "That's nice art. I wonder what the shirrt is about". it's a subconscious thing and we can't help it.
- Something that covers three quarters of the shirt.
- Something that stigmatizes people. The first thing people notice about a person is their clothing and the way they look. So making a shirt is - and this sounds astonishingly stupid - quite a responsibility,since you're the one who tells the world who the wearer is.
So here's what you could do:
- The simple route would be to just put the site's logo on the chest of the shirt and offer a light and dark shirt. Black and white are not bad choices for they are basic enough to not distract from the logo. When making a shirt that is - to an extent - an advertisement for something, the fabric itself should not be distracting from the "main event".
- Put a symbol that represents the site on the chest and the site's logo on the sleeve. People always underestimate the sleeves on shirts and think that they're just "sort of... there". But the things on the sleeve should be small, since they're a real eyecatcher. People are not used to seeing something on a sleeve, so they're bound to look at it.
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