I believe that comfort always wins when it comes to style.  That doesn't mean that I'm living in leggins and baggy t-shirts....all of the time.  It's easy to dress up a  striped tee and jeans to look pulled together.  Most importantly, you have to feel good in what you are wearing.  There is nothing more appealing than confidence.  

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You do not have to spend a fortune to look incredible.   Don't spend your money on trends.  Target & Old Navy are great places to find on trend pieces at fantastic prices.  Big ticket investment items should be timeless.   You'll get a lot of wear out of a great pair of leather boots or leather purse.   

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Style should be fun and not stressful.  A thought out, well organized closet will save you so much time getting dressed.  I know first hand that more stuff definitely doesn't make it easier to get dressed.  Keep only things you really LOVE and make you feel good