I am so lucky that Missy loves dressing up. She willingly sticks her head through the shirt holes, and puts one paw through the arm holes at a time. She really enjoys it, but I started dressing her when I got her at 7 weeks of age. She's pretty much ALWAYS dressed, unless it's a very hot day. She's well behaved when I am doing her hair too. She wasn't always that way though. I was very patient with her. I'd do her hair, she'd take it out, I'd redo it, she'd take it out, I'd redo it....finally she gave up
Maybe you could try putting a shirt on Lily and taking her out for a little walk as soon as she puts it on. It will distract her and reward her at the same time.
