6. The Chronograph Watch — Investing in a great watch is the perfect way to feel better about your everyday outfit. But, you don't need to break the bank if you don't want to. From Tommy to Tag, these tickers will keep you on time and looking cool, regardless if you're looking for a right-now piece or something you can pass on to your grandkids. And, this season, it's all about the Chrono — because, really, the more numbers, the better.

Tommy Hilfiger Men's Classic Brown Leather Strap Watch, $155, available at Tommy Hilfiger; Tag Heuer Stainless-Steel Chronograph (c. 1960s), $3700, available at Park & Bond.