Princess Gracie loves wearing her dresses, shirts, and fleeces. I said Yes, all the time but obviously not during the summer months. HRH has a couple of fashion shows in the Pix and Video section here on EBN. Lari makes many of her outfits for her... they are the best!
No ....never. I don't think dogs should be dressed.
When I lived in NY I would put a sweater on my dogs during the brutally cold winter months for their comfort, not my enjoyment.