Fashion Questions About Extra Skinny People

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Okay, I know this isn't the common complaint, but I am entirely too skinny. There's nothing I can do about it. I eat more than the average man, I just can't gain any weight. I couldn't even hold onto the weight that I gained during three pregnancies. At about 5'6", I weight 100 pounds. I know that I look almost sickly because of my weight, but I deal with it because I have always been this way. Believe it or not, being too skinny can be just as frustrating when it comes to looking good in your clothes as being overweight. Does anyone else have this problem? If so, what are your fashion problems? I never wear shorts, for example. My legs are just too skinny and it makes me look awkward. I have a question though... Can someone this skinny (with very long skinny legs) get away with wearing skinny jeans with tall boots over the top of them? I love that style and has always wanted to try it, but I picture it not working out for someone shaped like me. Any experience?