aww, don't be so down on yourself. remember that a smile is your best accessory! anyways, on to answer the question: i suggest getting a haircut somewhat like this: http://gas13.ru/v3/tutorials/hair9.jpg but i'd keep the color you have, it's very pretty and looks good with your skin tone and eyes. (also, that green shirt looks great on you!)
next i suggest a bit of mascara to make your eyelashes really pretty, you can use maybelline define-a-lash. then, for eyeshadow, i suggest a pretty brown, such as this on the girl in the picture: http://makeup.lovetoknow.com/Eye_Shadow_for_Brown_Eyes_Black_Hair
for blush, just a touch of this will look great: http://www.maccosmetics.com/templates/products/sp.tmpl?CATEGORY_ID=CATEGORY15104&PRODUCT_ID=PROD7518 in lilicent
for lips, i think this would look fabulous! http://www.revlon.com/ProductCatalog/ProductDetails.aspx?CategoryID=2&SubCategoryID=7&ProductID=29 in sheer petal
concealer for undereyes: http://www.revlon.com/ProductCatalog/ProductDetails.aspx?CategoryID=2&SubCategoryID=7&ProductID=29 in fair
I think you should wear contacts on special occasions, and your cute glasses for everyday.
There you go! Any more questions? Feel free to send it to my otherwise unused email: beccaboo3290@yahoo.com
Hope I helped! =)
p.s. The products mentioned were merely examples, you don't have to stick to that brand! One thing to remember though, when dealing with concealer, liquid is always best!