Finding a cute vacation dress that works for poolside lunches, sunset cocktails and strolls through town is a real challenge, but that's why we're here. We scoured the internet to find these 21 chic dresses that have a breezy, high-end flair, and start at just $10. Whether you're cruising, touring, beaching or some other combination, these stylish outfits are sure to carry you from the ocean to the city market in style. While these elevated vacation dresses give off 'luxury resort' vibes, we guarantee that they're also comfortable for all-day wear.