I rode a 380 mile (600km) brevet last year in jean shorts with no problems at all.

I've been wearing cycling shorts on a few rides (Mostly because they're for my cycling club to show support) and I can't say I'm really all that impressed... I wear them to advertise for the club.

I can barely do 30 in jeans.

That and I believe the team stuff is champ sports. Not well renowned for the best quality.
I am only going to pick up a jersey during the next order. My butt is picky.

heh heh... jean shorts.

Since I switched to a Brooks saddle, I'm just as comfortable in cotton shorts as in lycra, but the cotton gets soaked and is still wet when I go to put it back on in the afternoon for my ride home. Kinda uncomfortable. Of course, within 10 minutes the lycra would be wet anyway so it doesn't matter that much.

I'll stay with something that wicks as a base layer in the winter though, in case I wind up walking.

D2 and Dataj - Nice one guys now how do I clean the red wine I spatted off of my LCD comp screen?

Thanks for the opinions! I guess I'll spring for MTB shorts and try them sometime in the near future, although I kinda resisted cycling shorts before since I didn't like the squishy feel of a gel saddle and I expected padded shorts to be similar feel. I am currently using several bikes with old leather saddles (a Brooks B17 and a Sella Italia Condor ) which are both reasonably comfortable in their "worn in" states (but my commute is only 13 kilometers each way).

I used to be a huge fan of just wearing whatever street clothes I would normally wear on my short commutes. With jeans, however, it gets uncomfortable for me after only a few miles.

Lately, I've worn a wicking shirt and shorts with mesh inside whenever I've got to get across town. Nothing fancy. Certainly nothing that makes me look like a serious cyclist. It's cooler. It's really visible. My legs get some sun. Otherwise, I'd have legs as white as my old man.

I'm thinking of investing in a decent pair of sunglasses, though.

That statement is more than a little misleading. For one thing, he's not talking about commuters, he's talking about people doing stuff like "ride my bike across the USA". For another thing, while (according to him, and this is purely his assertion) these people don't wear dedicated cycling clothes, they also don't tend to wear what you'd wear just walking down the street. In any case, I'm not sure how the example is helpful for you as a commuter in making your decision about what to wear.

I spandex shorts under my regular shorts. I'm not really the cyclewear type either, but I hate chaffing.

I ride to work in my work clothes (khaki pants and a polo usually). Most days I do wear my cycling shoes (SPD) and bring my normal shoes in a pannier though.

I've done pleasure rides up to 40 miles long this summer in cotton cargo shorts with no padding and no appreciable discomfort. I usually do wear cycling shorts though for long (30 mile+) rides. I don't want to get 30 miles out away from home and start chaffing.

On the recommendation of a friend who does a lot of backpacking, I have ordered a couple articles of merino and smartwool clothing recently. I've never owned any so I just ordered a couple of shirts. I want to try it out before I invest a ton of money upgrading my wardrobe. I'll have to really feel like it provides a lot of benefit to shell out the dough for more. That stuff ain't cheap.

I usually wear padded cycling shorts on my commute, with some gym shorts over them, cuz I don't like to show off...

Today I wore my regular boxers with cargo shorts because my only pair os cycling shorts were still wet from hand washing them last night..and a little stinky too (not quite laundry day yet). I started to get some chafing towards the end of my ride this morning (13 miles)... just riding around my neighborhood I just wear the regular shorts with no problems though.

My biggest issue with wearing regular khakis or cargo shorts is that I'm in freakin HOUSTON! There is no way. They would be so soaked with sweat, they would look horrrible when i got off the bike. Much worse than anyone things bike specific shorts look. That's why i like the baggy bike shorts... they look normal but perform well for cycling.