On Thursday, Jenner showed off her knack for classy summer style while walking around the paddock with Joe Harper, CEO of the Del Mar Thoroughbred Club in a red-and-white sleeved wrap dress.
Jenner also observed the ages-old tradition of rocking a massive hat. Although, the reality star kept things relatively mild, opting for a wide-brimmed sun hat instead of the tower, flower-covered fascinators many traditionalists bring out for the big occasion.
Jenner has frequently opened up about the challenges she's faced since her transition in regards to elevated expectations from the public about her fashion choices -- especially considering the years she's spent living with her couture-conscious family.
However she keeps on showing the world that she certainly has an eye for styles that work for her.
At the ESPY Awards on Wednesday, Jenner showed off her classy taste in a white Atelier Versace gown that echoed the elegant old-Hollywood look of her Vanity Fair photo spread in June. For a look at her powerful speech, after being presented with the Arthur Ashe Courage Award, check out the video below.