If you have any jeans that say "relaxed," "baggy," or any other synonym of "loose," burn them (or, more preferably, donate them to a good cause). Instead, buy a pair of nice fitting, straight legged jeans. Levi's 501's are a great choice that match affordability with good fit and durability.

You should probably throw away most of the t-shirts you currently own. Just do it. Don't think about it; just grab them all and stuff them in a Goodwill bin. To replace them, get some nice, quality v-necks and crewnecks. To start, I suggest a few v-necks. They hide better under other clothes and look classier when you wear it by itself (or under a jacker).

There are just two things you need to keep in mind when shopping for fancier pants: your size (your real size, which you can get from a department store) and flat front. *Most* men don't need the pleats. These Docker's pants are a great first choice. They are not the most progressive choice, but you pay a lot for "better" cut pants (if you want modern, then I suggest Ted Baker or Thomas Pink).

If a tie is too stuffy for your environment, then a pocket square is a perfect choice to add a little pop. These silk ones from Jos A. Bank are beautiful; choose your favorite color and tuck it in your lapel pocket. These are $18, but if you hunt around, you can often find them *very* on sale (I bought a bunch for $1 the other day!).