Fendi’s Peekaboo x 9

Introduced at the beginning of the It bag era, this didn’t seem intended for a long runway. Not because it wasn’t good-looking or useful (it is) but because It bags were designed to hold women’s interest for a year or two – not 10 years. Designed by Silvia Venturini (the brand’s creative director of accessories and menswear, and the third-gen and only remaining Fendi at the fashion house), the Peekaboo is 10. Keeping it relevant to diverse women, in a very crowded bag market, is no small feat. How did she do it? With as many interesting iterations as possible. The only thing that hasn’t evolved is its raison d’etre: The bag remains practical, with two main compartments, whatever its size. – RT 

Regular Selleria in leather, $6,950.