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.
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.
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