Henleys and tees were traditionally undershirts as well. Fashion evolves. I would never wear a tank top outside of the house myself, but it’s still a shirt. Maybe a little trashy to wear in college but also, it’s where a lot of people test social norms to find their style. I’d say it’s fine.
It might be able to do it but it’s absolutely the wrong tool for the job. That’s Adobe Illustrator territory for sure and maybe inkscape can do it (not familiar enough with it to be able to say) but vector art creation tools are what you really want for this kind of thing.