I typically wear progressive glasses (with transitions) for normal daily wear at work and at home, but for riding or other sports I wear soft contacts (one reading, one distance since I am in my late 40s and both near- and far-sighted!) with sunglasses over. I have the cycling sunglasses with three different color lenses, which really helps for different light conditions. The darkest tint my regular glasses get to with the Transitions is not really dark enough for riding on the road (my eyes are very light-sensitive), and there's the peripheral vision issue that others have mentioned, so I highly recommend contacts with multi-lens sunglasses for riding. I wear Focus Daily disposable contacts, which are nice since you just toss them out after that day -- no cleaning or solutions needed. They're pricier, but not bad if you don't wear them all the time.
Good luck!
Emily
Emily
2011 Jamis Dakar XC "Toto" - Selle Italia Ldy Gel Flow
2007 Trek Pilot 5.0 WSD "Gloria" - Selle Italia Diva Gel Flow
2004 Bike Friday Petite Pocket Crusoe - Selle Italia Diva Gel Flow