Flying south for the winter ✨ If you’re planning a warm-weather escape, these resort outfit ideas are designed to take you from travel day to poolside lunches, beach afternoons, and sunset dinners with ease. Think breezy dresses, elevated swim, lightweight layers, and chic accessories that feel effortless but pulled together. These looks are perfect for winter trips to places like Palm Beach, Naples, 30A, Harbour Island, Turks & Caicos, St. Barths, Cabo, or the Bahamas—anywhere sunshine calls for relaxed, polished style. Save this for vacation outfit inspiration and easy resort packing ideas you’ll actually wear. ResortStyle VacationOutfits WinterTravelStyle WhatToWearOnVacation ResortWear WarmWeatherGetaway TravelStyle WomenOver40Style LTKOver40 LTKTravel