Kris Jenner and her younger boy toy Corey Gamble had a double date night with designer Tommy Hilfiger and his wife since 2008, Dee Ocleppo, at Craig's in West Hollywood on Saturday night -- and boy, did they make a stylish foursome!

The momager did not disappoint with her ensemble, wearing a body-con dress with sheer slits, a choker, and sunglasses despite it being late at night. This grandma is always revving to go it seems! Corey donned a light blue Polo shirt and light blue jeans (we can only assume the preppy look was in honor of his dinner with the king of prep).

On the other hand, Dee kept warm in gaucho pants, heels and a Kanye Pablo jacket. So trendy! Tommy himself looked chic and classic in a button down shirt.

We love that they all rode in the same car -- but did they really have to make Corey drive?! Seems a little tacky if you ask us!