According to the weather, it's still summer in NYC, but last year I was caught in a downpour that made me wish I had some waterproof gear. As cliche as it is, a trench is timeless and adds an instant element of class to any outfit. I happen to have a super lightweight one I can toss into my big bag (see tip #5). As for cigarette pants, they're the new skinny jean—so flattering and so retro!