My dogs own almost as much clothes as my kids and I won't even go into the amounts of collars(for id tag use only), harnesses, leashes, charms, bows and belly bands they have.
Neither one of my dogs minds wearing clothes and half the time they are shivering if they aren't because they are so small and one is half hairless due to being Yorkie x chinese crested.
I don't care if someone laughs

they're my dogs and if the "cruelest" thing I do to them is dress them up then so be it. The way I see it is that there are millions of truely abused, homeless, etc animals that would probably wish that their worse problem in life was wearing clothes.
I say that if it isn't really bothering your dogs and it makes you happy then that's what you should do.

Although my husband will only take the boys out in public with him if they are in all skull gear.