You Are The Advice Columnist: How Do I Dress Myself So I Can Look And Feel Confident?

I never feel confident in what I'm wearing, I need some major clothing advice

Apr 17, 2014 at 6:30pm | Leave a comment

 
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 I need help managing my image. Externally, I mean. Internally, I'm happy with how I "look," so to speak, but externally, I feel like a total slob. It might sound a little arrogant, but I'd like if my appearance, fashion-wise, could be as cool as I think I am... 
 The problem is, I'm totally clueless about dressing myself. I know what looks good on other people, however when it comes to my own clothes, I always find myself unsatisfied. My body shape is kind of odd in that I'm a bit taller than average, slim, and very top heavy. I don't feel comfortable in tops that show off my cleavage, nor in bottoms that reveal too much of my long legs. I also dislike baggy clothes, or clothes that cover up too much. No matter what I'm wearing, either I feel like I'm being unprofessional and revealing too much of my body or unfeminine because I'm completely covered up in something unflattering. 
 The clothes I'm most comfortable in are skinny jeans and men's white undershirts: in that sort of outfit, my legs get accentuated a little, and the curves on my chest are neither completely invisible nor directly in anyone's face. But I know I can't wear those clothes out, and to be honest, I'm a little embarrassed of them. I want to look like a put-together, confident woman. My clothes don't do me justice, and it's completely my own fault. 
 I don't really like accessories, make-up, or cute hairstyles. I've always been pretty tomboyish, in the sense that I don't like to spend too much time getting ready; I'm definitely a throw-it-on-and-go kind of girl. I like dresses and skirts, but I feel like they show too much of my body, so I can't really wear them. I also like to feel like I can run if I need to (what if there's a spontaneous butterfly that needs chasing?), so skirts that are too long or too tight are no good for me. 
 To me, my body is a very private thing. I love showing myself off to my partner, but I don't want the world staring at me and seeing too much. At the same time, I want to look the best that I can, and I know that at this point I just don't. How can I dress myself better? Please give me some advice.
 
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