Look at any old photo of the Rat Pack and you'll see it. That disheveled cool of being slightly mussed up. Like you actually live in your clothes. It's a look that makes you think, I want to be that guy. And you can be that guy. It's a simple, subtle trick that once you embrace, will make dressing that much easier. Who wants to worry about getting your tie perfect when you can knot up a simple, four-in-hand (already slightly off-kilter) and forgo tucking the tail into its fabric holster? It's a look we've been noticing more and more on stylish guys and realized that it's something that anyone can try with guaranteed success. The tie here is by the Windmill Club, a new line by Harvard senior turned designer Kevin Burrows. He just debuted the line of slim ties, which are handcrafted in Los Angeles from dead stock silk. Ideal for imparting the perfect preppy nonchalance.