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29 isn't old - you are prime. High heels are always good with skinny jeans to elongate your legs. Try a black 4 inch simple classic pump perferably spike heel and a jacket that comes to the middle of your bum and you will look terriffic. This year boots are hot so tuck your skinny jeans in your boots. Key is not to look like a lightbulb - right jacket and heels take care of that.
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