My pal Ashley Ruprecht, a former model and current graphic designer, on West Broadway street in NYC, sorta looking a bit Mad Men'ish -- though I've never actually seen the show, I think it fits? The dress is VINTAGE of course, sunglasses by GIAMBATTISTA VALLI, and the bag & shoes by PRADA.

Next is a guy in Sydney with a bright orange hat and nice fall layers, Amelia Dunbar in Williamsburg BK in a sleeveless WEHRMANN BLUES top, blue HANJIRO skirt, and boots all bought in Tokyo, a dude in London wearing severely shredded jeans with a black jacket and other black things, Berrin in Chicago in a white poofy blouse with a black inkstain and black LOOMSTATE skirt, and a guy in Tokyo in all kinds of colors and textures.

Follow Phil on Twitter: @MrStreetPeeper