If we examine the history of lip gloss and its impact on the beauty industry, we’ll see that some of the most notable and nostalgic makeup looks of the times involved a clear, hi-shine pout. They enhanced the appearance and plumpness of the lips––and often, were paired with a liner to complete. New York City-based makeup artist Jaleesa Jaikaranexplains that one of the most iconic lip gloss looks, in her opinion, comes from none other than the late singer and entertainer, Aaliyah. “ Aaliyah’s ‘Try Again’ makeup is so iconic to me,” she tells ESSENCE. “The glossy lips balanced out the makeup so beautifully. A lip liner and gloss is definitely top tier.” The minimalism from the ’90s and 2000s proves itself to still be relevant as many of us remain obsessed with recreating our favorite pre and post-Y2K beauty moments.