So younger sister Ashlee is making the most of her beach time as she plays in the sand with her four-year-old son Bronx.
The newly-single actress, who split from boyfriend Vincent Piazza last month, looked like she was reveling in spending time with her family in Oahu.
Fun in the sun: Ashlee Simpson and her son Bronx Wentz play on the beach in Hawaii on Thursday
The mother-of-one accessorised her casual beachy look with a black fringe purse, Ray Ban sunglasses, and gold hoop earrings.
Earlier that day, the singer teamed a tiny pair of denim shorts with a loose white tank top over a black bikini as she joined her mother Tina Ann for a shopping trip on Oahu.
What's so funny? Ashlee looks like she having a good time with her son and friends
Unconditional love: Bronx hugs his mother
Not joining the pair for their sunny outing was her older sister Jessica, who used the holiday vacation as a chance to announce her second pregnancy with former American footballer fiancé Eric Johnson.
The tall footballer was seen cradling their seven-month-old daughter Maxwell Drew as proud Aunt Ashlee played with her four-year-old son Bronx, from her marriage to rocker Pete Wentz.
Building sandcastles: Ashlee and Bronx lark around with the bucket and spade
Where's the bikini? Ashlee wore a Police T-shirt and skirt for her day on the beach
The I Am Me singer has also dated TV presenter Carson Daly, actor Tyler Hoechlin, singer Ryan Cabrera, and actor Wilmer Valderrama.
Aloha! Ashlee Simpson continued to spend quality time with her family in Hawaii Thursday, where the 28-year-old singer joined her mother Tina Ann for a shopping trip on Oahu
Laid-back style: The young mother-of-one accessorised her casual beachy look with a black fringe purse, Ray Ban sunglasses, and gold hoop earringsThe Simpson family has been reeling ever since news broke of Papa Joe Simpson’s gay sex scandal in October, but the minister-turned-manager tweeted that he was in fact spending the holidays with his family.
Though the 52-year-old has not been photographed in Hawaii, he has written three posts saying otherwise.
Joe wrote after posting: 'Wonderful Christmas. Spending special time and I am going to be a papa again!! Blessing from above. Spending Xmas wish Ashlee. Best if times.'
Bat boy: On Wednesday, Ashlee engaged in a playful game of tug-of-war on the beach with her four-year-old son Bronx, from her marriage to rocker Pete Wentz
Next generation of Simpsons: Meanwhile, her sister Jessica's NFL fiancé Eric Johnson cradled their seven-month-old daughter Maxwell DrewThe reality starlet is currently working on her fourth studio album, which she describes as 'a little soulful, a little electronic' with Grammy-winning producer John Shanks.
Ashlee also recently shot the film Pawn Shop Chronicles in Baton Rouge.
The action-comedy, due out next year, stars Elijah Wood, Paul Walker, Brendan Fraser, and Matt Dillon.
Expecting again! Jessica used the family's holiday vacation as a chance to announce her second pregnancy