As we enter the final month of InStyle’s 20th anniversary year, we’re taking a look waaaay back at our star-studded cover archive—and offering five lucky fans a chance to win a chic tote bag featuring an exclusive sketch by Donald Robertson. We teamed up with culturalist.com, a site that lets you create and share top 10 lists on a range of pop culture topics, for a look back at our cover collection. Take a peek at all of our covers, then make your own top ten lineup and share it on Twitter and Facebook using the hashtag #InStyle20 and you'll be automatically entered to win a tote bag. Need some inspiration? Check out InStyle editor Ariel Foxman's picks here. You must create and share your list by Dec. 14—so go ahead, play favorites!