Honestly if you're lost just look at pictures of people who look really stylish and start trying to copy their outfits. Go in WAYWT and save the pictures of people who look excellent. Start reading some fashion blogs and saving pictures of outfits that look good -- like sartorialist.com or streetetiquette.com. Don't feel like you have to copy an entire outfit -- approximate to the best of your ability with the clothes you have. Save outfits even if the overall fit sucks but there's a particular piece that really stands out. At first you will suck (like I currently do) because you don't have enough good pieces in your wardrobe, and you're missing some key essentials that are required to put together what you're trying to emulate. But you'll still probably be better off than your average American turd who clearly just doesn't even try. And then hopefully someday you'll actually be good at this stuff and have a solid wardrobe. But, like so many talents, I think the best road for a newbie is to emulate, emulate, emulate. Find people who are doing it right, and just copy it. Eventually it'll start seeping in and you'll actually pick up some understanding. edit: As an addendum, I think it's important to remember that you won't be good at this stuff right away. You wouldn't expect to pick up the guitar and become a virtuoso overnight, and the same goes for style. You won't start looking super stylish overnight -- it'll take some practice and probably a lot of errors before you start killing it.