We WISH We Dressed Like This At 14 — & Now, Too

If we had the styling chops of Mad Men's Kiernan Shipka when we were 14 years old, high school would have been a very different story. While our sophomore-year ensembles consisted of picks from local shopping malls and department stores, Shipka counts designers like Delpozo, Peter Pilotto, and Prabal Gurung among her wardrobe regulars, so it's no wonder we're obsessed with everything she wears. This nautical getup is no exception: A Breton-stripe top and navy, crepe shorts are polished and thoroughly foolproof. With summery Tory Burch wedges and a quirky, eyeball-print clutch, you, too, can dress like this super-fashionable teenager. Class dismissed.

Iris & Ink Striped Cotton Top, $60, available at The Outnet; French Connection Penny Plains Collared Top, $58, available at French Connection; J.Crew Pleated Crepe Short, $75, available at J.Crew; Falconwright Eyeball Print Clutch, $68, available at Need Supply; Tory Burch Alyssa Wedge Heel, $325, available at Tory Burch.