My hubby's a typical boy and would never wear exact matching outfits with me, but way back when we were dating I did get him to wear couple T-shirts with me just once. My hubs growing up in Japan loved Uniqlo, but when we were dating there weren't too many stores in the States. They had them all over Korea though, so when I was there studying one semester, I made sure to stop at a Uniqlo and bring back matching T-shirts. We wore them in public exactly once haha.
Now that we live in Cali, Uniqlo is readily available to us, so we got to go over to the Stoneridge Shopping Center in Pleasanton to pick out some couple-esque outfits just like five years ago :)