Personally, I have no problem with team kit. I'm Canadian and there are very few of us in the pro peloton so I'd happily wear a Garmin jersey because of Ryder Hesjedal (if I could find an inexpensive one). If he switched teams I'd happily wear that jersey as well, assuming it wasn't completely ugly. If I could find a nice, inexpensive La Vie Claire or 7-Eleven jersey I'd wear that as well because of Steve Bauer and Alex Stieda. I can't see myself in full kit, but a jersey for sure. I also wear my team's jersey when I go to a hockey game or to watch a game at a friends house. That jersey has the team logo only, no name or number on the back. I wear the jersey to support my team, not a particular player, which differs from how I support cycling. In that case it's more to show my support of the cyclist on a particular team. As for leaders jerseys (yellow, pink, polka dot, etc.) I would never wear one.

You can't control what other people think about you so wear what makes you feel good.

Cheers!
K