We imagine it’s particularly difficult to be yourself when you’re constantly in the public eye. Not only are your sartorial and beauty choices scrutinized every time you leave your house or appear at a high-profile event, but your romantic life is immediately put on display and judged by everyone who witnesses your choices. And this doesn’t just apply to Hollywood starlets and B-list reality TV favorites—the fashion community has had its fair share of controversial couples who have been slammed in the gossip columns.
From industry power players like Jenna Lyons and girlfriend Courtney Crangi to Vogue editrix Anna Wintour and her entrepreneur beau Shelby Bryan, there’s been tons of tabloid fodder surrounding folks who you usually think about simply for their street style merits and enviable careers.
In honor of incessant gossip regarding Calvin Klein getting back together with his 23-year-old boy toy Nick Gruber, we decided to take a look at the industry’s 10 most controversial couples of all time.