We imagine an evening at Three Dots and a Dash means you'll be skipping over some domestic brew options and heading straight for the cocktail menu, selecting something refined along the lines of the Pago Pago. In keeping with the ladylike tone you'll be putting out there, we recommend a pencil skirt and heeled sandals. Plus, the cutout bralet will show off the last of that summer tan. The final touch is a fall-ready lipstick that's still vibrant enough to channel the Bahama Mama in you.
Suno Jacquard-Knit Pencil Skirt, $335, available at Net-A-Porter; Topshop Cut-Out Bralet Top, $34.23, available at Topshop; Ardency Inn Modster Long Play Supercharged Lip Color in Lucky, $25, available at Sephora; Jimmy Choo Fedora Sandals, $1,050, available at Jimmy Choo; Forever 21 Spiked Fringe Beaded Necklace, $12.80, available at Forever 21.