Drake has learned a few things about tailoring since he first came on the music scene in ill-fitting jeans, but it doesn’t seem like he’s going to stop wearing sunglasses indoors anytime soon. Thankfully, the world’s coziest celebrity might never let go of his deep appreciation of sweaters. This week the rapper released a “playlist,” full of Caribbean-inspired beats to match his Nancy Meyers–esque linens. If there’s one staple to Drake’s wardrobe it’s athletic jackets, ranging from leather biker styles to varsity silhouettes. See the Canadian in his best outerwear, Tom Ford tuxedo, and more in our slideshow ahead.