So I've browsed the pictures here and got some ideas but I couldn't find much text commentary about dressing in matching clothing when riding your tandems. I understand that there are certain times that you would almost certainly dress alike (such as a team ride wearing team jerseys). I'm not interested in the situations where rules/customs dictate wearing a certain outfit, only what you wear when you get to choose your own outfit for casual/just-for-fun riding.
My wife wants to match when we ride our tandem on the local MUP. I have no strong feelings about it one way or the other so we're reverting back to the first rule of tandems- do whatever the stoker wants. So far our best "matching outfit" will consist of bike shorts and matching t-shirts as we've yet to agree on a jersey that is affordable and available in our size(s).
How about you- Do you and your stoker intentionally wear matching outfits when riding 'just for fun'?