I won't wear anything that is too blatantly saying in word how much of a furry I am.
No Babyfur stuff.
I will only wear a shirt with an extremely cute picture if there is a visual joke people around me will get.
I mostly wear the Hyena Agenda shirts just about everywhere because they're just that cool no matter where you wear em. I usually hope someone will ask about it. It's happened a few times.
I have a few furry theme shirts with a video game joke at my side job where I sell video games and movies.
Shirts with my character, convention shirts, or anything else topical in the fandom at the time at furry meets.

Agreed on the Hyena Agenda shirts :3
How do you normally explain it when someone asks? Do you mention furry to them?

What sort of thing is extremely cute? Like this? https://www.furaffinity.net/view/10823342/ Cuter? Are you worried people will look down at you for wearing something that looks like its "for kids"?

Honestly I'd wear something with an extremely cute design. Never had a bad comment. I sometimes get looks but that's part of the fun don't ya think? :3

I have told people about what furry is but people act like they don't know what I'm talking about.
Yeah. That fox shirt is too cute. I actually have something equally cute one with a wolf cub playing with paint that happens to be the wolf from Okami so it works for my side job at the game shop. I guess cuteness can work if it's something recognizable.
I have worn a shirt with a photo of a fursuiter.

Where did you get the wolf shirt? That sounds like something I'd like!
A shirt with a photo of a fursuiter? Where did you wear that? Funny, I wouldn't hesitate to wear an extremely cute shirt but I'd hesitate to wear a shirt with a fursuiter on it! It might make people wonder "why" and also all the bad CSI stuff.

I think you should wear more cute shirts. You often get positive comments :3

I got the Okami Wolf shirt at Anime Expo in Los Angeles.
I wore it at my other job where I sell video games. The fursuiter photo shirt also had a Cadilac CTS in it. We had the new Need For Speed game so I wore it as an educated joke. I don't know if anyone got what I did but it was funny anyways. There was no bad response from it.
When you said CSI, that does remind me. I did some random suiting with a female suiter and some guy thought me and her were gonna do things with each in suit. The comment was "My wife and I do freaky things too". There was some awkward silence and we moved on.
I do mix in a few cute shirts in there. The Okami wolf shirt scored big and a few people got the visual joke. The guy I worked with even sort of recognized the character.

Oh cool, you're a suiter? Yeah, there's all sorts of awkward situations around fursuiters. I'd be more hesitant to wear a shirt with a photo of a fursuiter than a whole fursuit! Maybe I'm paranoid! :3

Still surprised you'd wear a fursuit photo shirt but not a cute fox shirt!

It's O.K. to wear a shirt with a fursuiter on it. It's depends a lot on what it is. I never did wear that shirt at any fur meets. Only to my other job at the video game shop. I did have plans on getting a photo of my own fursuit on a shirt but never got around to it. I do have a few with drawings of my fursona done by me and other artist.
I think Fox shirt might be about having a good visual joke for it. I can tell it's supposed to be a play of Fire Fox. I just remembered that I do have a cute "What Does The Fox Say shirt" which is in one of my photos. There was this one shirt I missed out on from Guilty Fox that had a cut fox on it with the words "Foxes Are Guilty"
Some of my convention shirts are cute. I have worn those at both furry events and non furry events.

1. Would wear in public. It's discrete yet stylish.
2. Would definitely wear in public. Cute but not specifically tied to a fandom.
3. Most definitely would wear, especially since I use Firefox and it's very cute.
4. Would not wear in public or private. I am not ashamed of being a furry, but when people meet me for the first time I want them to know me for my personality, not a fandom I belong to.
5. Cute. But no. See above.
6. Cute. I would wear among close friends and at a con. Hesitant to wear in public.
7. You already know my thoughts on this one.
8. Hesitant. I may have somewhat of an interest in vore, but this crosses the line into "wearing your fetish on your sleeve" territory. Maybe if there was version that didn't have text on it. Then it might be funny.

Cool, we have similar preferences :3

I'd hesitate about wearing 4. Don't really like to shove furry in people's faces. I'd wear 5! To an outsider it makes no sense, it doesn't shout "I'm a furry"! Agreed about 8. Lose the text, make it more comical than fetish.

I'd wear 6, would be fun to wear! Are you worried about the message it sends? Do you think you could ever wear it in public?