How to be Smarter: Woot.com for incredible, once-a-day deals.
How to be Prettier: For the warmer months, nice tan/camel/nude heels look better than wintertime black. Same goes for jackets.
How to be (less) Awkward: No dancing to an iPod while walking down the street. Foot tapping, head bobbing -- all fine. Dancing to music only you can hear (in the literal, not metaphorical way) seems a little vain.