The lovely ladies, who attended the New York City gala with their mom, Kris Jenner, showed a whole lot of leg and then some in two very racy dresses.
Khloe bared nearly all yet was still covered up in a sheer Yousef Al-Jasmi dress that featured silver branch-like sequined embroidery, while Kourtney wore a black strapless gown with a bustier top, ruffled skirt, and thigh-to-knee cut-outs along the sides of her legs. Both were adorned in Lorraine Schwartz jewels.
Even though the pair sizzled on the red carpet, Khloe apparently wasn't feeling great about herself. Despite showing off her dress on Snapchat earlier in the evening...
...once they were in a taxi to the event, the 32-year-old denim maven aired a few frustrations about how she looked.
"Kourtney will not stop videotaping me, and I look literally like a hippopotamus and a whale had a baby. Mind you, Mario [Dedivanovic] said I look like a f**king ice skater, while Kourtney looks like gorgeousness..." Khloe said over a series of selfie videos.
She then turned the camera on her sister and exclaimed, "Look how bomb. Oh my god, see? Fuego, this one. Gorgeousness. Stunning angel."
In one of the many Snapchat videos Kourtney took, the mom of three even joked about Khloe not wanting to be videotaped, to which her sister replied, "Because I'm like a f**king beached whale and you're making it more difficult."
Then in a later vid, which the 37-year-old reality star dubbed "Taxi Cab Confessions," Khloe reiterated, "Why would I want to do a red carpet if I feel like a fat slob? Why would you?"
Once inside, however, Khloe got in the celebratory mood once again. After all, the charity gala benefits Gabrielle's Angel Foundation for Cancer Research, and last night's event memorialized her father, Robert Kardashian Sr.
The Kardashian family was seated at a table with Kris' boyfriend, Corey Gamble, family friend Jonathan Cheban, and Tommy Hilfiger, who presented a tribute video dedicated to the late attorney that was set to Kanye West's song, "Only One," and featured home videos. The memorial brought tears to Kris' eyes before she took the stage to accept an award on Robert's behalf, with Khloe and Kourtney standing by her side.
Though the evening was an emotional roller coaster, Khloe and Kourtney found some solace in a favorite activity on Tuesday morning -- shopping! The duo held hands as they visited Tommy at his brand's headquarters, with Kourt even snagging a sweet '90s throwback jacket, which got a major smile out of the designer.