Since I was 12 years old, I've been shaving my legs for cycling. I've missed a few years along the way, due to injuries and a short break from cycling after high school. Still, for the better part of 24 years, I've been putting razor to skin at least once a week and very often 2-3 times a week- especially during the racing season.
There was a time when I was a kid and in the early years of my racing carreer when I sincerely believed that I was going to turn pro and be the next LeMond. In fact, when I began shaving my legs in 1982, LeMond had just gotten 2nd at the road World Championships (he won his first World title the next year).
Over the years, I've grown comfortable with the knowledge that I will not ever win the Tour de France or the World Professional road championships. I'm fool enough to still cling to the hope that one day I could maybe win the Masters World Championship on the track... it's still my dream (I just have to outlive all of my competitors).
In the 24 years that I've been shaving my legs, I've answered the "why" question more times than Jack Abramoff handed out checks to Republican Congressmen. That's a lot folks... At my advanced age now, I probably shave my legs as much for the reason that it's just "what I do" as much as any "real" reason.
In the early days of cycling, riders shaved their legs for multiple reasons; one was to allow bandages to stick to the skin better after crashes (which were frequent at the time) and the other was to ease pre and post ride/ race massage (no painful hair pulling). As things modernized and races were won by tenths, then hundredths and now thousandths of seconds, shaving became more popular for aerodynamics. Many riders now even shave their arms- especially for important time trial races.
For those of us who don't have to worry about pre or post race massage or winning or losing big races by narrow margins, shaving is the number one way we identify ourselves as cyclists in this world. Other cyclists know we are "serious" about our sport or our riding because they can see our smooth legs. Granted, we could just be swimmers or triathletes, but the legs look different usually (and they usually have the upper body strength that most cyclists never will). It has really come to be a cycling status symbol more than anything else. It is the badge of seriousness, dedication, passion or belief. Over the years I have known many guys with shaved legs who you'd never ever know rode bikes otherwise. Shaving sets us apart from the unwashed masses of non-cyclists (or those dirty little mountain bikers who don't shave).
Cyclists on group rides without shaved legs are frequently marginalized due to their "Fred" (goober) status. The funny thing there is that I have also known some guys who could kick most pro riders to the curb in a race who had hairy legs. Walk in to a "pro" bike shop with hairy legs and it might take a few hours for a salesperson to acknowledge your presence. Walk in with shaved legs and you might still wait forever, but you have better chances anyway.
I've been shaving my legs for so long now that I don't know if I'll ever be able to stop. Each time I stop for a while, the hair just freaks me out and I feel dirty and gross. And I'm pretty neurotic about the shaving too- I've been known to get pretty upset if I find that I've missed any offending hair after a shave. My wife, bless her amazing heart, is less worried about her legs than I am of mine... which raises some concerns about my mental stability. I'd dare say that I am the one most likely to offer our daughter tips and advice when she begins to shave her legs. (Daddy is already her wardrobe assistant after all.)
So whether you shave your legs or not, enjoy each and every ride you take. I'm gonna keep obsessing about my own shaved legs, but I won't pass judgement on you for having hair or just a little stubble. Either way, you're part of my weird little family and I love you just the same.