To cap off the summer, Jennifer Lopez took her 18-year-old twins—whom she affectionately calls her "coconuts"—on an Italian getaway before they head to college this fall. In said shot, she embraced effortless vacation style in a striped J.Crew shirt dress—a timeless warm-weather staple that's as practical as it is polished. For the remainder of summer, a shirt dress pairs effortlessly with sandals or ballet flats. Once temperatures begin to cool, layer it with a crewneck sweater, a statement jacket, or your favorite boots for an easy transition into fall. While Lopez's exact J.Crew style has already sold out, we've rounded up similar options you can shop now.