Kylie Jenner Vs. Ariel Winter: Which Young Star Rocks Hotter Date Night Looks? By: Farrah Julin November 8, 2017 8:06AM EST 1 of 5 Kylie Jenner Kylie Jenner & Travis Scott matched in maroon pieces on date night. (SplashNews) October 24, 2017, 11:11PM 2 of 5 Ariel Winter Ariel Winter wore tiny booty shorts on her Halloween Horror Nights date night with Levi Meaden. (REX/Shutterstock) October 24, 2017, 11:11PM 3 of 5 Kylie Jenner Kylie Jenner & Tyga looked red hot on their date night. (SplashNews) October 24, 2017, 11:11PM 4 of 5 Ariel Winter GICA / BACKGRID Ariel Winter wore this stunning white dress to Levi Meaden’s birthday party. (Backgrid) October 24, 2017, 11:11PM 5 of 5 Kylie Jenner Kylie Jenner & Tyga matched in army green on their date night. (SplashNews) October 24, 2017, 11:11PM Click to Subscribe to Get Our Free HollywoodLife Daily Newsletter to get the hottest celeb news.