Gridskipper

Though they won't win any prizes for customer service, Barney's Co-op offers a wide selection of jeans. If your man needs a really good pair of well made jeans, bring him here, have him try on at least a dozen styles… (even if he complains the whole time), and he'll find something he looks great in. With denim, it's always good to be able to see all of the high end brands next to each other for comparison. [link]

This is a great gateway shop for the somewhat messy inexperienced shopper in your life. The clothes are casual and easy to like -- let's call it high style streetwear-- so the store presents a great first step for… someone accustomed to t-shirts and sweatshirts. You won't find anything exorbitantly expensive, nor will you find anything too fancy. [link]

Uber-hip Freeman's Sporting Club is meant to be the ultimate store for fashion forward yet masculine men. The aesthetic is 1930s backwoods manliness, if that makes any sense. The tailoring is some of the best in… the city, so it's a good place for collared shirts and well tailored coats. This shouldn't be the first stop for your novice man however, as some of the clothes are on the pricier side. He'll need to be eased into that. [link]

The store is small, but you'll typically leave with something you like. The cramped shelves teem with t-shirts, flannel shirts, and all manner of vintage button downs and jackets. They also feature an excellent… and incredibly affordable vintage boot selection. They won't last your man forever, but for $50 a pair, they won't have to. [link]

When I made the rounds shopping with my non-fashion-loving boyfriend, INA was a real hit. The eclectic selection of vintage designer clothes offers a lot of options, and each piece is well made and well cut. Items… here will definitely last more than one season of wear, and the prices are reasonable given the quality. The selection of cashmere and wool sweaters is especially strong. [link]

This small and spare shop off the Bedford stop in Williamsburg has excellent albeit slightly expensive clothes for both men and women. It's a little easier for men to shop here as the store stocks a number of reasonably… priced sweaters and ties. The styles are chic but not too prissy, so your BF will still feel like a man when he leaves. [link]

Odin, the male answer to the eclectic women's clothing boutiques all over the East Village and Soho, is a must stop for fashionable men in New York who care about well made unique pieces. The prices range from reasonable… to expensive, so it's one of those stores to hit once a season for staple picks. They carry great jeans (Cheap Monday, Kicking Mule), Band of Outsiders ties, Common Projects sneakers, and Trovata slacks, along with a whole selection of shirts, sweaters, and t-shirts. Both the store in East Village and the one in Soho are worth a visit. [link]

Again we have a store where you, or the boy, will inevitably have to drop some serious cash. However, the clothes are classic and built to last. Just buy one signature piece and see what it does for his wardrobe.… Come here for Opening Ceremony's newly launched denim line, comfortable but sleek shoes, and original pieces from both underground and well known designers. The store usually picks designs from a certain country each season, and right now you can find all the chicest designs from Sweden. [link]

If you're willing to dig around a bit, Tokyo 7 will be the most rewarding of the stores on this list. Almost all of the clothes are vintage designer the store gets on consignment, so everything is well made and… marked down. As a bonus, they have plenty of vintage dresses and shoes for you to try on while your man searches for a good blazer. [link]