Dressing like a man, but not taking yourself too seriously, is a skill. Clothes you wear between seasons can be especially tricky. But just a few key elements will take you a long way. Keep it simple: Light scarves in neutral earth tones have made their way to NY from Europe and South America and are now a staple. Light leather jackets work just as well as cotton blazers and hold up better in the rainy Spring. Skinny belts are a cinch when shown or hidden beneath shirts left untucked. Meanwhile watches are getting bigger and meant to be seen from across the street.

Monarchy

Tommy Hilfiger

The sailor thing can look downright ridiculous if you’re trying to look like, well, a beatnik French sailor. Try channeling your inner JFK instead: Go with sailing inspired stripes on a lightweight sweater with an updated cut. Keep the nautical theme in mind when choosing a blazer, great for tee and collared shirts alike, and lightweight sweaters that will spare you from carrying a jacket around. Pants are still running closely fit this year, but relax: You’ll have room to swing your bat. Finally, casually soled shoes in colors like stone and clay work with jeans and un-suited professional attire. And they hold up with our without socks.

Michael Kors

Remember what your dad wore on Saturdays? It wasn’t an ascot or microfiber. It was plaid. Just like you used to wear when it was still the 90s, money was good, the Internet was free and your best friend wasn’t married. Relive those grunge days in plaid of better fitting, more finely woven, cloth. It still works with slacks or shorts, socks or not, tucked in or out, and the favorite jacket of your choosing. In other words: Saturday.
Nicholas K

CREDITS:

Photography: Chris Wells, LIVE at Fashion Week NYC
Layout and Design: Laura Varrone