I strongly urge anyone doing a sprint or olympic tri... TO WEAR TRI SHORTS and A TRI TOP.
This will save you so much time and hassle in the transition area. When you have other stuff to think about, why worrying about changing all those clothes?
Tri shorts and a top will take you from each event without thinking twice about what you are wearing.
Messing with shoes, socks, helmets, race belts, etc... is more than enough.
Yes, I know the tri shorts have no padding... and are not as comfortable and regular bike shorts.
BUT... here is how I see it... what's 1 hour of my life in a little discomfort? It's nothing. I'm not riding 50 miles, I am riding 10-15 miles. Very short distance... so why bother with being absolutely comfortable? I just wear the tri shorts... and do it.
And trust me, I have a very sensitive butt- or really boney sit bones...because my butt hurts after wearing bike shorts on a 20 mile ride!
But, I figure I am racing... not out for a casual ride... and I can suck it up (Suck it up buttercup!) for 15 miles.
NOTE: This advice does not apply in cases where it's cold. I'm all about putting on more clothes when it's freezing outside. Whereas, some won't even do that.
"Life is not a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather, to skid in broadside thoroughly used-up, totally worn out, and loudly proclaiming: WOW WHAT A RIDE!!!!"