History has an odd way of repeating itself. Around Dec. 2013, Harry Styles and Kendall Jenner were rumored to be dating after getting dinner together and even taking a ski trip together the next month. Around New Years of 2015, the pair were seen on a yacht together in St. Barths acting all cute and couple-y again. To put it lightly, Jenner truly has everything: fame, fortune and Harry Styles.
The two were first rumored to be dating in Jan. 2014 while skiing in Mammoth Lakes. They were spending a weekend skiing with friends and, of course, they were acting all cute. However, they both ignored dating rumors and never confirmed or denied them.
After their ski trip, they were spotted a few times after that in London and New York. Styles and Jenner were also seen talking with Cara Delevingne at the British Fashion Awards in Nov. of 2014. Styles has been rumored to have dated Delevingne, but that didn't cause any awkwardness for the trio as they talked for a few moments at the BFAs.
Since they called it quits the first time, Styles and Jenner weren't seen out and about together until recently. They have been pictured together while on a vacation in St. Barth's with a number of guests including their mothers, Ellen DeGeneres, Portia de Rossi and a number of friends.
Styles reportedly invited Jenner on the trip along with some of his friends for New Years. There are several pictures of the couple cuddling and swimming with friends. On New Year's Day, both Style's and Jenner's mother, Anne Twist and Kris Jenner, came aboard to spend time with the couple. DeGeneres and Portia de Rossi made an appearance for lunch during the trip.
Styles and Jenner looked cute and perfect and everything in between on their vacation. They looked happy and looked like they were having a good time in photographs. The couple looked relaxed and carefree while enjoying some time off.
Although I hate to admit it, they're almost as cute as Styles and Taylor Swift were. Almost. Congrats Kendall, you've got everything: the looks, fame, fortune and Harry Styles.

























