I second What Not to Wear! They have a book, too.
Mostly looking good in clothing is about shape. Get something that fits--really fits (i.e. not too baggy in the shoulders, waist or bum). Second most important thing is color and how you pair colors. Get flattering colors--you won't look good in all colors, so try on a few. Then look at the colors you put together and make sure they go together. Sometimes a colored shirt just looks dowdy next to black pants, but might look great next to brown, tan, or gray slacks. Shoes can dress up jeans for a more polished look. A jacket can do that too.
Good luck!
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