Fashion - Going Out (Without Coming Out!)

[MrWookie]

I've been thinking about making another fashion thread since I learned so much when I started a thread on jeans a while back. I'm looking to pool 2+2's collective knowledge to get some better ideas on what to wear "out." "Out" means many things, and I am looking for ideas on most all of them. We already have a thread running on business dress, so we don't need to focus on that here, other than, for example, differences in your choice of suit between going out and going to work. I have no doubt that discussion of specific brands will come up, and that's certainly good, although I would like to focus more on getting the right look than getting the right label. Here are some questions and ideas to kick things off:

You're on a first date with a girl. You're meeting for a cup of coffee. What do you wear? Does this change if you're going to a bar for a couple drinks?

One outfit I've seen mentioned here is a designer t-shrit, sport coat, and jeans. What goes into the choice of each to properly "rock" (as they say) this look? Or perhaps has this already entered the realm of the passe?

Speaking of which, what are common fashion mistakes made by 18-35 year old males? What things have gone out of style that are still seen far too often (for example, tapered-leg jeans)?

Where do you draw the line between label-whoring and getting good stuff? Where can you find good stuff if you don't quite have the balla roll of a SIHB or the esteemed forum sponsor?

You're going out to a party or a club or whatever where a suit and tie is definitely too formal, but you still want to dress to impress. What do you wear?

Shoes: beyond sneakers and basic dress shoes, what do you look for, and how do you pair them w/ the rest of your outfit properly?

What are some simple ways for a t-shirt and jeans guy to spice up his wardrobe a bit?

And by request, how do the answers to the above change if you're (a) skinny, (b) muscular, (c) slightly overweight, or (d) obese?

These are some suggestions to get things started, so if you have additional questions along these lines ask away.