The 'Sundress Challenge' and the associated 'Railed in a Sundress Season' catchphrase are viral internet tropes that resurface annually as spring transitions into summer. Originating largely on Twitter and TikTok, the trend blends fashion appreciation with suggestive humor, highlighting the cultural obsession with the aesthetic and physical appeal of sundresses. While 'Sundress Season' began as a simple celebration of warmer weather and breezy outfits, the internet quickly added a more provocative layer, turning it into a 'challenge' that signifies readiness for summer flings and romantic encounters. The meme is typically used through reaction images expressing excitement, thirst-posting, or humorous commentary on how the garment shifts the social atmosphere of the season.