I got my butt handed to me by a heavily bearded guy wearing below-the-knee cut off dockers and riding a no-name 1970-s bike boom bike with Single speed drivetrain and knobbies. I have respect for him and enjoyed racing with him.
I regularly get my butt handed to me by my buddy on his Motobecane. I have respect for him and enjoy racing with him.
Bottom Line: Gear that does not get in your way is good gear. Get out there and be fast and suddenly it won't matter what other people think of your gear.
WHY? Because FAST = GOOD
Cyclocross is one discipline where I insist on going out and having a good time regardless of my fitness level or gear. And it is a great sport for doing just that.