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I'm kind of in the same boat...I'm girly about certain things but other things not so much lol...I love make up but I can't dress myself for crap...I am a t shirt and jeans type of person and i'm plus sized and pear shaped so that makes buying clothes difficult. My boyfriend used to laugh at me cause I had a pair of harley davidson biker boots that I wore around all the time (even though I've never even been on a motorcycle lol). He was like "don't you have any girly shoes?" ....and the answer was no lol

There is a book by Lucky magazine called "The Lucky Shopping Manual: Building and Improving Your Wardrobe Piece by Piece" which has awesome tips for how to find stuff that looks flattering...you could probably find a cheap copy of it on amazon or ebay. I've put some of the tips to use but my clothes are still kind of plain and tomboyish cause I don't have much money to spend...but at the same time, I'm pretty happy with myself and don't want to change entirely, so the world will just have to deal with it lol