Yes there’s the perfectly named UglyChristmasSweater.com, which recently unveiled a tool that allows buyers to design their own unique ugliness. Because let’s face it: everybody’s ugly really is their own. The UglyChristmasSweater site was started in 2012 and just won a feature on CNN because of the new DIY ugly tool. But they aren’t the only ugly sweater game in town — not by a long shot. There are some heavy hitters in this space, even though at first it might seem pretty niche.
One of those big players is Shark Tank‘s Robert Herjavec, whose investment in the quirky apparel company Tipsy Elves has become one of his favorites. Herjavec is the Shark who’s quickest to smile — and though ugly sweaters and IT Security (where Herjavec made his fortune) don’t have much in common he’s a natural fit for the cute and cuddly brand. The Ugly Christmas Sweater is a trend that has somehow endured, first popping up as a cultural phenomenon in the 1980s. Now not only are the niche brands like Tipsy Elves in this space, but everyone from the custom makers at Etsy to the big retailers like Kohl’s and Macy’s offer a category of Ugly Christmas Sweaters. Ugly doesn’t just have to mean graphically jarring either. In the Bad Santa tradition it can be a depiction of ugly holiday behavior, like the “Ugly Christmas Sweater – Yellow Snow Sweater” featured at Amazon. It’s Safe For Work, but probably not the sweater to wear if you’re looking for a promotion. It’s all big business, too, as well as fun. Herjavec doesn’t just like the spirit of the enterprise; he likes that Tipsy Elves reportedly sold $12 million worth of ugly fun in 2014.