10 Looks: New Fashion, Vintage Ideas

1950s

The lesson: Invest in a structured, ladylike handbag.
 
 The background: Although it was designed in 1892, the Hermès saddle bag didn’t make waves until 1956. That was the year Hollywood royalty (and real-life princess of Monaco) Grace Kelly was photographed carrying the boxy style to shield her pregnancy from the paparazzi, sparking a craze for the newly christened “Kelly bag.” Today you need to get on a waiting list for an Hermès bag, but this design in red patent leather offers the same kind of classic sophistication that will turn heads years from now.
 
 To buy: Lulu Guinness bag, $570, luluguinness.com. Paul Smith Black Label dress. Giles & Brother by Philip Crangi bracelet.