Who likes to iron? Nobody. Which is why Steven Alan's signature rumpled look wins us over time and again. Since opening his first eponymous shop in Soho in 1994, Alan, a native New Yorker, has steadily expanded his empire with boutiques scattered across Manhattan, Brooklyn, and East Hampton as well as three stores in Los Angeles. His famous relaxed-fit button-downs, which come with reverse seams and twisted plackets, are perfect for the guy who wants to look fashionable without appearing as if he tried too hard. Alan also makes great skinny ties, comfortable trousers, casual jackets, duffle bags, vintage-inspired scarves—you name it. And everything proudly comes with the Made in the U.S.A. label. The shop also stocks top brands for men, such as Engineered Garments and Woolrich Woolen Mills, and a killer selection of vintage Rolexes. For the dude who hates to shop, a major plus is the friendly, knowledgeable staff, who direct their customers to the right fit and style. The store also offers excellent sample sales twice a year that are a must for great deals. And guys, Alan also has an excellent line for women—you know, just in case you want to buy something for your lady. 103 Franklin Street, 212-343-0692, go to stevenalan.com for more locations (10013)