Jerseys are functional as mentioned, but technical wear will serve as well, minus the pockets.
Proper cycling shorts are the way to go, period. You can always carry a pair of baggies to put on if you are afraid of being seen off the bike, but you'll get over it. I need to lose some weight, and I could care less what anyone else thinks. Surely you can get over it, too. The chamois serves not only as padding, but also wicks away moisture. Your junk will thank you for it. With your cardio conditioning, you'll have to ride long for it to be effective, as you pointed out. Anything over an hour in the saddle, you're gonna want proper shorts.
Whatever glasses will be fine. I rarely wear any myself, and occasionally pay for it with a bug in the eye. I've just never been able to find any pair of glasses that don't hurt behind the ears after 15 minutes.
"It hurts so good..."