Take a quick scroll through your friends' Instagram pics, and chances are you’ll see more vacation 'grams than everyday shots. While it totally depends on the person, most of us are guilty of oversharing on vacation when the weather — and our strategically planned wardrobe — is on point. If you're anything like us, this is because you like to go ALL OUT on vacation — and we're not just talking about the sightseeing. While some dread the idea of packing, others choose to turn this chore into a fine art. Whether it's shopping for the perfect cabana-to-dinner dress or selecting the most versatile, Insta-worthy bag to tote around town, all of the effort pays off when you're touring a new city or relaxing on the beach in a “totally you” ensemble. Now, wouldn't it be amazing if all of those looks could send you on your next vacation? Well, thanks to Cotton, this dream could come true for three lucky readers. Just post your very best cotton travel outfit with #StyleOnTheFlyContest, #CottonFavorites, and @discover_cotton for a chance to win $4K toward your next trip and all-new vacation wares (or $450 for two lucky runners-up). Just include why your unique look is your favorite, and you're set! Check out your competition here.