Sock boots have been a standout among the style set for some time (continuing their streak this season), yet another silhouette with old-school sensibility is now stepping into the spotlight: slouchy boots. Reminiscent of a late ’80s to early ’90s aesthetic, they were prominently featured on fall runways (Saint Laurent, Off-White and Isabel Marant to name a few) with the most wearable versions in understated leather or suede and cut for a loose fit. Pairing the scrunched silhouette with slim-fitting jeans feels like a no-brainer, but we’re also fond of teaming it with dresses and skirts. Here, our edit of the best slouchy boots to buy now, from mid-calf to over-the-knee. And since they’re hitting It-boot status come fall, we suggest getting in on the trend before it sells out.