I have a couple of padded shorts but rarely wear them. I've found that for the biggest comfort factor is having the right saddle adjusted to the right spot. I have 2 Brooks (B-17 and C-17) and 2 Selle Anatomica saddles and once I got them dialed in on their respective bikes, I don't have any discomfort even on long rides in regular clothes. Comfort is such a personal thing that I wouldn't discourage anyone from wearing padded shorts or call them a wuss for it, but as a general rule I would recommend first getting the most comfortable (for their butt) saddle fitted as perfectly as possible, then worrying about whether you need padded shorts only at that point.