Supermodel Kendall Jenner and her billionaire sister Kylie kicked off the new year in style with a little vacation in Aspen with their closest friends, including Hailey & Justin Bieber, Anastasia Karanikolaou, Jaden Smith and more.

The sisters officially took ‘winter chic’ to new levels thanks to an assortment of outfits and styles worn throughout their trip to Aspen. Kendall can be seen below bringing a whole new level of style to horse riding, opting for a full leather outfit including an aviator jacket with a fuzzy trim, sleek leather pants and tucked in leather boots.

The 27-year-old 818 tequila founder finished off her look with chic accessories, including a fluffy black earmuffs and stylish shades.


The intimate friendship circle partied in style on a ranch in Aspen over New Years Eve, with Kylie turning up the heat pairing a vintage fur-trimmed coat over an Alaïa lace jumpsuit for the night’s festivities.

Kylie Jenner


The weekend snow trip was anything but ordinary, with the group of high-profile celebrities not only showing off their winter style, but what goes with it; snow trekking, skiing, partying and celebrating all that New Years Eve has to offer. Social media star Hailey Bieber offered her fans a “holiday dump” of photos from the Aspen getaway, including an intimate photo with her poster husband Justin Bieber, and a dancing clip from New Years Eve festivities.


The Jenners have long been fans of horse riding, growing up around horses and competing in horse riding competitions. As revelled on the season two finale of The Kardashians, Kendall says she has plans to one day convert to the “cowgirl life.”

“I have a lot of ideas and a lot of things I would love to do in life, so I’m excited to continue to explore all these things, but … I’m moving to a ranch,” she said during a confessional on the November 24 episode.