The Craziest Moments From The Kardashians' Aspen Trip

If you've been keeping up with the Kardashians at all, you know that they love documenting every moment of their entire lives — and the family's December 2018 vacation to snowy Aspen, Colo., was no different. Kim Kardashian and Kanye West brought kids North and Saint (and possibly Chicago, who wasn't pictured), while Kourtney Kardashian and Scott Disick took their own tykes, Mason, Penelope and Reign along — as well as Disick's girlfriend, Sofia Richie. Awkward! Kendall Jenner also tagged along. Former Kardashian BFF-turned-frenemy-turned-pal-again, Paris Hilton (Remember when she said Kim's infamous behind looked like "cottage cheese inside a big trash bag?"), even turned up for some cold weather fun.

From shopping to skiing to being incredibly underdressed for the temperatures (but really, what else is new?), the first family of reality TV ended 2018 in a predictably big way: Here are the most ridiculous moments from the Kardashians' trip to Aspen.

On Friday, Dec. 28, 2018, Sofia Richie flew in and joined the Kardashian family trip — and she, Kourtney and Kourtney's baby daddy Scott Disick all went out to dinner together, because that doesn't sound awkward or anything. However, a source told E! News that the unlikely trio actually spent a bunch of time together on the trip and that "everyone has accepted Sofia at this point and she has been able to tag along and be a part of the family activities."

It wasn't the first vacation that Richie (or Kourtney, depending on how you look at it) third-wheeled. A week earlier, the potentially cringeworthy crew went on a group trip to Cabo San Lucas, Mexico, with Disick and Kourtney's three kids, and the tropical getaway reportedly went well.

"The first day they all hung out together with the kids at the beach," a source told E! News. "Kourtney, Sofia and Scott were all chatting and enjoying the day. Scott was in the middle of Sofia and Kourtney and they were lined up on chaise lounges. Scott got up to play with the kids and Kourtney and Sofia were chatting. They look like they are on very good terms and there wasn't any tension."

Disick summed it up well in an Instagram snap of his ex and new flame in Cabo, writing, "What more can a guy ask for? THREE'S COMPANY."

When Kanye West joined his wife, Kim Kardashian, as well as Kendall Jenner and Kourtney Kardashian for a shopping excursion in Aspen, he seemed woefully (yet also joyfully) under-dressed compared to the ladies.

Kim wore a sheer, see-through striped top under her black coat and slim-fitting Balenciaga "pantashoes," The Daily Mail reported, which are glossy, black Spandex leggings that have the brand's signature "Knife boots" at the bottom — and will set you back a cool $2,850 if you can manage to get your paws on a pair. Jenner wore black tight pants, white Adidas socks and a black coat with white sleeves speckled with gray, while Kourtney rocked head-to-toe onyx.

West, meanwhile, opted for light heather gray sweatpants, a black coat, a blue plaid shirt, a red beanie, dark gray socks and matching kicks. He seemed to be at least sort of in on the joke, because he tweeted a now viral photo of himself in his normcore best, sporting a goofy grin, and holding up a shirt and shoes from a store that were nearly identical to his own. 

Kim Kardashian rocked a hot pink Prada ski suit and matching shades, of course (above left) over a black turtleneck with black gloves and boots to hit the slopes in Aspen with sister Kendall Jenner (who kept it casual in black, white and gray) on Dec. 29, 2018. If you wanted to cop Kardashian's conspicuous style, The Sun estimated it'll set you back about $2,900.

The next day, Kardashian went skiing once more, this time with daughter North. Kardashian wore head-to-toe black (and goggles so huge "they resembled a VR headset" per The Sun), while North rocked hot pink this time, from helmet to suit to gloves with black boots. The tab also caught snaps of North riding on her dad Kanye West's shoulders (above right) as well as sharing a ski pole with her mom. Another style note: Kardashian's long brunette hair (possibly extensions) was down seemingly for the entire trip, so one may assume she stuck with the bunny slopes, because it surely would have gotten in the way on a black diamond.

Kendall Jenner started a bit of a trend among her sisters when she ventured outside in the snow wearing an itsy-bitsy-teeny-weeny pink bikini with a furry, cream-colored hat, black boots, and sunglasses. She posted two snapshots of her skimpy ensemble on Instagram with the caption, "f**k it's cold."

After Jenner posted her bikini pics, big sister Kourtney Kardashian posted two photos on her own account, rocking a teeny-tiny silver bikini under her matching puffer coat with similar boots to Jenner's. In one photo, she shows herself from the front, and in the other, she gets very cheeky — literally — and flaunts her backside, which is largely bare due to the small style of her bikini bottoms. Her caption was simply, "Copied Kendall."

For the record, the high temperature in Aspen the day the photos were posted, Dec. 30, 2018, was a whopping 29 degrees Fahrenheit. Here's hoping the ladies weren't unclothed outside for too long.

It turns out, Kourtney Kardashian and Kendall Jenner had a bit more to cover up with than a bikini in the snowy Aspen weather. On New Year's Eve, the eldest and arguably most low-key Kardashian sister shared Instagram snapshots of herself playing in the snow with her kids. In these shots, she's indeed appropriately bundled up, rocking a black beanie, a white puffer coat, black gloves, and weirdly reflective pants that came close to ruining her photos, which were evidently taken with flash during the evening. In the shots, Kardashian appears to throw snowballs with one of her sons, who is seen in a subsequent photo appearing to make a snow angel. Cute!

Jenner, meanwhile, did more than just pose nearly nude and ski on her trip. The supermodel also hit the slopes for some snowboarding action. Jenner took to her Instagram stories to show off her personalized, South Park-inspired board that reads, "Oh my God! They killed Kenny! You bastards!"

When Sofia Richie wasn't hanging out with Scott Disick and Kourtney Kardashian, she palled around with Paris Hilton — former Kardashian frenemy and former best friend of Richie's own older sister, Nicole Richie, with whom Hilton starred on The Simple Life.

Richie and Hilton rode the ski lifts together and cracked jokes. Richie said in an Instagram story (via The Daily Mail), "It is ice cold here, people. We're on a ski lift. She seems to act like we're in California," to which Hilton, 37 to Richie's 20, quipped, "I'm LA, b***h!"

Richie previously told Wonderland magazine of her friendship with Hilton, "It's really nice to have her kind of, as like a sister, because she's been through it all! She gives the best advice and she wants the best for me and she sees how my path is going. She's really rooting for me and giving me the best tips, how to avoid certain things and how to be the best version of myself that I can be."