I wear levi 501s because they don't have a fly, so it's one less thing to fuck up. They're also levi's so they're always in style, and they look good on me. I'd kinda like if they made some that were a little bit lower rise (long torso, my natural waist is way to high to effectivly wear pants at,) but it's a minor quibble that is only an issue when I get ones that are either longer, or were longer (used pants that were shrunk down.) 501s also, ahem, make all the good parts look better, which is an advantage...

I wear tshirts, (any color it doesn't matter it all goes with the jeans), and if climate, or etiqute requires more, I generally wear a dress shirt of some kind (all are neutral, most navy, or grey, a couple in a teal color, but it doesn't matter, becuase it's either over jeans or black slacks. And then sweaters in the cold parts (handknit, by me) Some are more ornate than others, but again, I haven't managed to come up with an outfit that I'm unpleased with.

Also, all of my commercially produced socks are black. They look more grownup without trying. Not to be worn with shorts, but I'm of the opinion that shorts and socks are a no-no. But I haven't owned a pair of athletic shooes in at least 5 years. Brikenstock Scandles/Clogs/Londons (clogs with a back). Make it work. I wear handknit socks in the right weather. They might clash horribly, but I think if you're wearing socks you made yourself, you're entitled to be eccentric.

When I buy new plain tshirts I generally, go for American Apearl shirts, which hold up great, and feel amazing, and fit great. They're also made in LA, but I'd totally buy them even if they were made in burma by small hungry childreen.

The key: have a system where everything works with everything else, and that requires minimum preperation. If you know you're not going to be able to iron dress shirts, *always wear sweaters;* similarly if you can't commit to ironing pleated slacks, buy unpleated ones. Also I tend to be of the opinon that one should maximize the use of black, (it's slimming!) and at the very least tends towards darker colors, where any eccentricities are appropraite. You could have tshirts that were every color of the rainbow, as long as your pants are all the same color, or variations on the same color. That's the basic hack, and you seem to have it.