Cash has sweaters for winter as it gets very cold here (no snow though). He is very cold without them and since we don't have central heating (not really used here in SA), I keep him in hoodies. He has some punkrocker ones that are soooo cute, complete with a skull!
June will also have sweaters for winter, but nothing for summer - only a bow for her. (No bow for Cash)
I think dressing them up in cute if it is more or less practical or holiday related.