Wear the clothes which make you happy. Don't second guess, if the jersey makes you smile, and every time you are thinking about it, you smile, you will be "the happy lady in the cute puppy shirt".

I wear things on the bike I could not wear on the street, I'm going fast enough not to hear any giggles, and it makes me happy!

My sympathies on your loss, and many happy years with your new pup.