Packing for Key West can be a bit of a challenge. If you've never been to the Southernmost City, you may be scratching your head and staring at your empty suitcase. In the Florida Keys, the year-round sizzling temps and the laissez-faire attitude call for loose comfy clothes with a touch of tropical panache. Luckily, the island is packed with expertly curated boutiques like Local Color, Fresh Produce and Wanderlust, which focus on natural fabrics and figure-flattering, flowy styles. Their colorful accessories inspire ideas for layering with chunky necklaces and graceful scarves. Isle Style and Green Pineapple carry similar clothing but with an eye on upcycled, organic and fair-trade fashions. Don’t forget the mother-ship of all resort wear, Lilly Pulitzer, which has the classic shift dress--a must for any beach wardrobe. For more trend-conscious shoppers Evolution and Blue carry top labels for men and women that you won’t find anywhere else in the Keys. Also fashion-forward, DeJaVu features younger, contemporary styles with a Boho flair designed by owner Stephanie Carter. Need more practical gear for on-the-water adventures? Stop by World Wide Sportsman in Islamorada on your way down to Key West. They carry outdoor apparel for men, women and children in trusted brand names.