I started dressing Chloe when I picked her up from the breeder. It was winter so I put a sweater on her and I had a little dress waiting for her at home. She was a little over a pound when we got her so very very tiny and I just bought doll making sweaters at the dollar store and WalMart for the first while since they were cheap. I did buy some splurges which only fit for a little while, but I couldn't help myself
A lot of her baby clothes still fit, actually...I mean they're too tight to wear for the most part, but even though she grew to be 4lbs she's still very petite.
Some dogs hate clothes, but if you start them as a baby it'll be what they know.
Chloe LOVES getting dressed, but she never minded it. If I grab an outfit she jumps around like a maniac and runs to the couch or bed and sits down. When I go to put something over her head she puts her head down for me and pops her own arms through the arm holes most of the time. If I leave a dress in her reach she'll bring it to me and growl at me with it in her mouth until I put it on her lol she hates to be naked