Ivan Nikolov / WENN

Molly Sims, in high heels, waves on the street

Model Molly Sims (left) waves from a New York City street as she arrives at the Mercedes-Benz IMG New York Fashion Week Fall 2011, and we are absolutely digging her groovy gold-colored jacket with the short sleeves. The date was February 13, 2011. Molly Sims was born in 1973, so she turned 38 the year this photo was taken. On the high-fashion front, we would just like to point out the soft leather boots worn by her friend, which still seem to be widely popular all these years later. We regard them as a baffling fashion item: they seem intended to look sleek and fancy-casual, but in practice they so quickly look worn and sloppy. They're halfway between Uggs and cowboy boots, not a great place to be. Of course it's hard to compete, fashion-wise, with a supermodel in high heels, but in general we feel that real hard leather boots, or absurd $800 sneakers, would have been a better choice here.

See our biography of Molly Sims