One of my new favorite brands is a perfect staple in your closet for the summer to fall transition weather. In Chicago, the weather ranges from 80 degrees to 60 degrees throughout the month of September and early October so dressing for the season is way trickier than dressing weather appropriate. Luckily, Endless Summer has a wide array of options that you can dress up/down depending on how it looks outside. They have cute matching sets, slip dresses you can throw a sweater over in the office, and sundresses you can pair with cute chunky/cowboy boots. Scroll through the gallery below to shop my picks!