For makeup - I'd suggest leaving your wallet at home, and going to a department store or an Ulta store for a makeover -don't go on weekends, especially not during the holidays and ask for a makeover -but be specific as to what your lifestyle is...
The makeup chick on What Not to Wear has a book out-the 5 minute face that doesn't look bad...
Moisturize moisturize moisturize no matter what are you are - protect your skin and forget about the tan - use a good self tanner if you must -what looks fine now -will look like shoe leater and not expensive italian shoe leather in 20 years...
at your age you do not need a lot of make up... - the pictures are tough to tell much of anythig but it - you've got good skin tone - just work with different colors and what looks good on you... bt a professional would be able to tell you (what we cant se i those pictures) what the underlying colors are and are you better i pink, reds, peaches, etc..
Fashion -ther's a thread inthis forum about the 10 essential elements about the articles of clothing that womena re suggested to have in their wardrobe -it's worth a read... but before you do that - go and get a proper bra fitting - there's a huge percentage of women out there that are wearing the wrong size bra or wrong style bra - and that can make the most expensive outfit look like crap - a properly fitting bra can make a tshirt hang properly...
Go to a few different stores and try on various outfits - in various sizes even stuff you wouldn't have ever thought of wearing before -and see what looks good on you... and do not get hung up on size -- every manufacturer sizes differently and only you have to know what size it really is...
have fun and go to a store and play