For me, style has to be effortless and comfortable without resorting to sweats and a tagless undershirt. Wearing a great pair of worn-in jeans can be one of the most comfortable pieces a style guy has. Key to success? The fit has to be right—slim and tapered and naturally washed out. Otherwise you risk looking like an old man wearing light-washed elastic waist jeans (I feel like these will be making a fashionable comeback soon…). These light-washed wonders have become one of my favorite go-to summer staples, and when combined with a basic heavyweight tee and leather chukkas with no-show socks create a simple summer look easy to emulate.