Originally Posted by RubeRad

Well guess what, I'm a dude that thinks all those MAMILs out there (Middle Aged Men In Lycra) look like idiots, and that's not stopping them.

If you buy a bunch of expensive kit, and then show up for a ride and find out it's wrong, then maybe you are an idiot. BUT, don't buy anything, wear what's comfortable, show up for a ride, tell people you're figuring stuff out, and maybe you'll LOOK like an idiot, but at least it won't have cost you anything. But more likely people will not be jerks and cut you some slack, probably give you some recommendations.

Another perspective:
One possibility: you show up in comfortable whatever and are slow: they'll think 'makes sense he's slow, he's just getting started'
Another possibility: you show up in comfortable whatever and are fast: they'll think you're slow at first, but then be impressed.
Another possibility: you show up in immaculate kit and are fast: they'll think nothing. Or that you're 'one of them' already
Another possibility: you show up in immaculate kit and are slow: they'll think you're a poser
Another possibility: you show up in expensive, but somehow 'wrong' kit, and are slow: they'll think you're a poser with no sense of style