Since I almost always wear sneakers or wingtips boots, raw Levis, decent fitting Tshirts, and a trucker jacket (saving up for the TOJ groupthink ), I never post in WAYWT (because it looks good but is v. boring) but its still good to see what I do/dont like from what other people do.
Edit: I saw shah's thumbs up prediction and didn't like the above photo because I didn't want to ruin it.
Good pair of boots + fitted jeans/tees + splurged outerwear and maybe a quality knit is really all you need. Eventually, when you reach the proper level, you migrated over to Men's Clothing. That's where the $$$ is.