When I first started putting clothes on my Chi, she hated them. She would wear them & then manage to get out of them in about an hour. Persistence is the key. I would put the shirt back on as soon as she took it off. It took a few weeks, but eventually she got used to wearing clothes & now she LOVES to wear clothes, no joke! She always gets really, really excited when I decide to dress her up
Good luck!
Amy