I always have been and always will be an outfit repeater. In kindergarten, my family took a weeklong vacation to Jamaica, and I packed one pair of pants: yellow cargos from the boys’ department at Gap. I wore them every single day of the trip paired with the only swimsuit I brought, which was a red Speedo one-piece. Almost two decades later, not much has changed—at least not when it comes to my proclivity to wear a select number of tried-and-true wardrobe items and then wear them a dozen more times with no shame.
These days, my tendency to wear the same things over and over has less to do with limited options and more to do with taste (and maybe a little bit of laziness). If I find something that I like that also fits me well and can be mixed and matched with my pre-existing sartorial regulars, I’m not just going to wear it once and then store it away until people forget. I’m going to get my money’s worth by styling it in every which way that I can.
If dressing this way has taught me anything, though, it’s that the pieces that do make it into your wardrobe rotation have to be versatile, season-less (for the most part), and fun to wear. After all, the goal isn’t to wear the exact same outfit day in and day out but rather to wear the same individual pieces in a way that makes them appear different with each look.
Keep scrolling to find out which 37 essentials I repeat again and again.