Originally Posted by carpediemracing

First, a tall wheel is faster in a cross/tailwind kind of situation, where it can sail. Shape isn't as critical. I don't use tall wheels for the headwinds, where everyone is going slow. I use them for the cross tailwind bits where I pick up noticeable speed. On windy courses tall wheels can make a big difference in top speed, and that's what concerns me. For a long time I favored my Specialized TriSpokes, aka HED3, and a rear disc wheel, especially in the really windy flat courses. In less windy but super technical courses I'd use my lightest wheels, not really aero (Zipp 340s), but super jumpy. I had Zipp 440s (58mm tall) but usually put the TriSpokes on instead. For road races, which I still did back then, I'd use a super light front non-aero (280g Campy rim or 330g FiR rim wheel) with a 440 rear (for the sail effect after I got shelled on whatever hill).