Clothing for the Transportation Cyclist?

I'm on a roll with the bicycle-related posts lately. Possibly it's because it's springtime and the car is falling apart, so I'm riding more, possibly it's because I think with rising gas prices, unrest in the Middle East and environmental catastrophe looming over our shoulders daily, I think it's important to explore alternate transportation method, or possibly it's because I know way too much about bicycles.

In any case, now that cycling has once again become my primary means of transportation, clothing choice becomes an issue. For just spinning around town, whatever I happen to be wearing is fine, and for long rides dedicated cycling wear makes sense, but for a seven-mile commute, meeting friends for dinner or other occasions that are far enough away that cycling comfort matters, but I when I also want to look like a human being at the end of the ride it takes a little bit more planning.

I think there are four things to keep in mind with transportation bicycling clothing:
1. Comfort on the bike - This is especially important with pants. Pants or shorts that restrict movement, have uncomfortable waistbands or badly-places seams are bad. Also they shouldn't get caught in the chain, which means baggy pants bottoms are out. I use a chainguard on my commuter bike, which means I don't have to roll up long pants, but on the other hand, dress pants with sewn-in cuffs still get caught on the chainguard itself.
2. Sweat management - This is especially a big deal during hot weather, but can be a problem in cold weather with layers as well. Cotton is particularly bad for this, because it tends to hold moisture in, but some synthetics, while they dry quickly, tend to smell funny when they're damp.
3. Weather - You should be able to adapt to a reasonable range of weather conditions without too much trouble.
4. Looks off the bike - Obviously, you want to look presentable once the bike is locked up and you have to interact with non-cycling people Wrinkle and stain resistance helps this a lot, as does a smart choice of color and style

I'm still searching for the perfect bike-to-work pants (there are companies that are trying to make stylish dedicated cycling wear, but not only does it not come in big-and-tall sized, it's pretty darn expensive, usually over $100 for a pair of pants). But have had some luck in finding the perfect bike-commuting shirts from an unexpected direction: golf. It seems modern golf wear has evolved away from tartan knickers and excessively loud sweater-vests to a more understated khaki-and-polo-shirt look. And since golfers are social creatures who occasionally spend their time out in the hot sun, they look for fabrics that shed sweat and wrinkles. Golf shirts might be pricey to begin with, but are often readily available at discount retailers, even in 2X sizes (golf may be a sport, but not everyone who plays is built like a 5k runner). So reasonably fashionable, quick-dry, wrinkle-resistant collared shirts are the easy part.

Aside from looking for the perfect pants (I'm envisioning something along the lines of Dickies 874 work pants, but with a gusseted crotch) I'm still searching for the perfect bike-to-work underwear. Without going into the gory details, moisture management and seam placement is key to avoid discomfort, and if you're going to ride to your destination and then spend the rest of the day on your feet, padded cycling shorts tend to have an uncomfortable "diaper" feel to them. So far my favorite has been a pair of briefs from EMS, but they're very expensive. I've also been looking into quick-dry Champion boxer-briefs from Target, but find they bind a bit around the leg holes, making them less than ideal. They do breathe fairly well though, and are comfortable in an upright, walking-around position, so they might work well for some folks.

Oddly enough, in the vast array of internet cycling lore, you can find billions of threads debating about carbon vs. steel frames, millions about whether you should ride Shimano, Sram or Campagnolo but very few discussion what to wear to ride your bike to work. There are some excellent bicycle-fashion-related blogs, but they're geared more towards the city cyclist who travels relatively short distances, and Velouria over at Lovely Bicycle has some good advice to offer for sporty womenss cyling wear for the non-Lycra set, but I'm looking for a bit more masculine approach. I'll keep working on it and share any profound revelations that I come across.