The scenario: you've been dating for weeks, things are going unbelievably well, and life is a bowl of cherries wrapped in a dream with a unicorn on top. It's not quite time to meet the parents (we'll get to that sartorial challenge in due course), but you've been invited for a face-to-face with the best friend.
Your ensemble's mission is two-fold: First, it should communicate the idea that you are non-threatening and that you come in peace, i.e., you are not going to hurt the object of your affection. Secondly, and just as crucially, it must also assert that you will not be a giant buzzkill for the friendship in question. It must convey a free and easy sense of low-maintenace, denoted by clothes that can easily transition from lunch, to happy hour, to a night on the town, all without needing to take a cab.
The above off-duty look from Australian model Jessica Hart achieves both objectives through a seemingly thrown-together combination of bluest-blue skinny jeans, undone high-tops, a wide-lapel khaki jacket and a leopard-print scarf. Create your own version with our picks below, and bring along a tiny terrier for good luck, if you can.
(From Left: Zip Jacket, $89.90 at Zara; Acne Studios Skin 5 Jeans, $250 at Barneys New York)
(From Left: Cheetah Print Scarf, $18.99 at Daily Look; Hi-Top Sneaker in Truffle Canvas by The Row for Superga, $295 at Jildor)