Dr. Mrs. Jill is the dog, see what I did there?

Hear me out, it's possible he wanted to wear a mask wherever so nobody would catch him on camera without one, like those pictures of Kate Brown (governer of oregon) not wearing a mask at a huge party

maybe he just has bad breath and Dr/Ms Jill made him wear it to protect the dog

With all the pics of him shopping in Nantucket last month without a mask, I can see his confusion.

Oh, ok