We have definitely decided to spend our 25th Anniversary ( next year) in Italy. Hunter has also definitely decided he wants to dress the part and needs new clothes. Must admit, I agree.
Not sure about your significant other, but I have a very limited window in which he is agreeable and not a whiny little three year old when trying on clothes. Also, if something works, we buy it in all shades available. So I shop on line, order, press, wait days for him to try on item, finally tell him he's not getting into bed until he tries on item, yay or nay, pack it up, ship it back, try again.
Since we are going to Italy, I have found out men do not wear shorts and men do not wear short sleeve button downs. I have also found out not to many men at all wear short sleeve button downs. According to Emily they just look funny. What about Dad? He's old. Old guys wear short sleeve button downs. Hunter's OK being old but I am going to try to ease him into a few long sleeve ones.
Saying: Don't worry about old age. It doesn't last long.
I do believe my work is done and this is now what his spring/summer wardrobe looks like: