I highly enjoy humiliating critters with funny clothes and such. The dark looks and grudging "I only tolerate this because I love you, you stupid human" attitude makes me laugh.
OTOH, I've run into many dogs that actually enjoy it because it's attention. Pearl loves getting dressed up and I practically had to chase my bosses bulldog down and pin her to get the pumpkin costume OFF of her. Getting lot's of "OH SO CUTE!!!" from the humans will get some dogs to put up with just about anything.