Button: Pride 2020

Perfect Guy Outfit: Richard Chai’s Chill, Winter Ensemble

If you couldn't already tell, we're pretty smitten with Richard Chai both for his designs and for his own sartorial choices. When we spotted him in this laid-back look on the street, we had to stop and take a snap for a little menswear — and layering — inspiration. The star of this outfit is an oversized olive khaki vest, paired with a simple flannel shirt tied around the waist to balance out the bottom of the ensemble. Simple straight-leg corduroy pants, a white T-shirt, and black Dr. Martens keep things casual, but if you want that extra-special high-end touch, add in your favorite leather jacket. Not only will the sheen of the leather elevate the outfit from basic to baller, it'll also keep you warm when that wind kicks in. Now, all you need to do is check out the items we've handpicked to make this cozy-cool aesthetic your own. If the temps stay as mild as they are, you (or your man) might be living in this get-up all winter long.

Dr. Martens Original Boots, $115, available at Shoe Parlor, 851 7th Ave (between West 54th and 55th streets); 212-582-0039; All Saints Horns Ss Cut Collar, $38.50, available at AllSaints, 411 West 13th Street #1 (between 9th Avenue and Washington Street); 646-862-3155; Rugby Ralph Lauren Naval Flannel Shirt, $98, available at Rugby Ralph Lauren, 99 University Place (between East 11th and East 12th streets); 212-677-1895; Oak Army Military Poncho, $218, available at Oak, 28 Bond Street (between Bowery and Lafayette Street); 212-677-1293; Quicksilver Joint Pant, $59.50, available at Quicksilver, 519 Broadway (between Spring and Broome streets); 212-226-1193.