When: 2018

Rocky’s love for Raf Simons, who used to be the creative director for Calvin Klein, is well documented. That’s why seeing him roll up to the Calvin Klein show during New York Fashion Week last year in a head-to-toe outfit from Simons’ 205W39NYC collection isn’t not shocking. The rapper paired an oversized striped sweater with burgundy trousers. The highlight of this fit is the bulky navy blue and olive green winter coat.