I think for cycling kits - wear whatever you like! I'm pushing 5-0 and PLEASE don't tell me I have to look at "sensible" solid colors. GAAAAK! I see so many cute jerseys.... and then there are socks!

For street clothes, I think there is some general age and body type guidelines - good sense - that some people don't seem to get. Thus the need for "What not to Wear". I don't want to dress like a matron, but I know I'm not a teenager either.