Picture the late-nineties nerd and what first comes to mind is a gangly teenage boy in khaki flood pants playing Dungeons & Dragons. Imagine, instead, a small girl in cropped plaid flares and a matching blazer, sobbing at the optometrist’s office. That would be nine-year-old me, a skinny kid teased at school—for wearing a fuzzy mink bomber instead of a North Face, for carrying a plastic binder of Pokémon cards—miserably holding a new pair of wire-rim frames.
I thought of that little four-eyed loser last February when I saw Alessandro Michele’s Gucci debut. The Gucci of my youth, of course, was the height of the Tom Ford era—slinky white jersey and little black dresses, all cool and confident. But here, Michele seemed to say, was the 21st-century Gucci girl, an eccentric, fresh-faced weirdo who wasn’t afraid to wear backless fur-lined loafers, to personify the idea of “ugly pretty.”