Ashlee Simpson's career started in the shadow of her famous big sister, Jessica. This is quite literally true, as her first job was being a back-up dancer for her sister, and it just felt true for most of the late 1990s and early 2000s. Ashlee was girl-next-door cute, but Jessica was the blonde bombshell. Ashlee had a bop of a song with Pieces of Me, but Jessica had the better voice and more hits. Jessica also had the hit reality show while Ashlee had the unfortunate Saturday Night Live incident.
It might be easy to think that Ashlee got stuck in the cute little sister role forever, but thankfully for her, she's all grown-up now and seems to be thriving on her own terms. A big part of that is the joy she seems to have found in creating her own sweet family. Ashlee has been married to her second husband, Evan Ross, since 2014 and together they are raising three kids.
Ashlee isn't one of those celebs who documents her entire personal life on Instagram, so it is always great to see the little glimpses she does share of the sweet family moments with her, her husband, her teenage son, Bronx, and Ashlee and Evan's two youngest children, Jagger and Ziggy. Scroll on for some family cuteness, and maybe do Ashlee a solid and stream Pieces of Me in the background!
Big Bronx
Ashlee's oldest child, Bronx, is now 14 years old and from the looks of this picture from Thanksgiving 2022, Ashlee is about to experience a quintessential mom-of-teens moment: the day when we realize that someone we gave birth to is now taller than us!
Big Family Joy
Ashlee and her husband have their own sweet family, but they are also part of a larger family that includes some awfully famous names. Yep, that's Evan's mom, Diana Ross, rocking red sweatpants with the rest of her family — including the delightful Tracee Ellis Ross.
Ziggy Blu Turns 2!
Ashlee's youngest child is son Ziggy Blu (who turned 2 in October 2022), and we think he might be the kid who looks the most like his famous mama. He is awfully cute, and we're sure that it feels like he is getting big way too fast!
Evan Has His Hands Full
They've been married since 2014, but Ashlee is still gushing about her love for husband. On Father's Day 2022, she shared this sweet pic of Evan holding their little kids and swooned, "You are truly our rock. Thank you for always making everyone laugh, and giving the best love. You make everything better. I love doing this life with you. DILF."
The Cutest
It doesn't matter if the dad in question is famous or not, we're always going to love a picture of a sweet (and very squishy) baby sleeping on their father's chest. We can sure see why Ashlee shared this picture, because it doesn't get much sweeter than this!
Sister Love
We love a baby shower, especially when it gives us a chance to celebrate with the other women in our family. Ashlee shared this great picture of her last baby shower that shows she was also enjoying the special time with her big sister, mom, and adorable nieces.
A Family Halloween
Yes, Ashlee and Evan's family is looking all kinds of Halloween cute in this picture (and, yes, there is Diana, looking ageless as always). But we're also distracted by the completely gorgeous sunset happening in the background!
Fun Dad Time
Evan and daughter Jagger Snow were having all kinds of fun racing on mini-tractors in 2021, and he wasn't afraid to let his competitive side show through in this sweet picture, which he captioned, "We WIN! Me and YOU." We're here for the fun dad energy!
Aww!
There are few things in life sweeter than getting to see older siblings holding their new baby brother or sister. This picture from 2020 shows the tender side of big brother Bronx as he cradles little Ziggy, who is all swaddled up. Awww!
Backyard Glam
While some of us might be lucky enough to have a backyard that includes a play structure, we suspect that most of us aren't looking quite so casually glam while we hang out in the yard as Ashlee and her sweet family do in this picture from 2020. We can all probably relate to little Jagger's desire to get twirly in her dress, though! We love a good twirl.
Beautifully Blended
Ashlee and Evan married in 2014, when Bronx (her son from her previous relationship with singer Pete Wentz) was about 6 years old. She shared this throwback snapshot from the wedding, showing one of their first moments as an officially blended family. So sweet!
Fatherhood Joy
Did we already include a picture of Ashlee's cute husband with a baby on his chest? Yes, yes we did. But did we warn everyone that we are a sucker for a man with a baby on his chest? Yes, yes we did. So, sorry but not sorry for including a second one. We can't resist the sweetness, especially when it comes with a caption that talks about Evan's joy in being a father: "How lucky I am to be a father/stepfather. I love you beyond infinity. Thank you @ashleesimpsonross for bringing this love into my life."
Waiting for Kicks
One of the fun parts of having a bit of an age gap between siblings is that the older kids can really understand what it means to have a new baby brother on the way and can also get excited about the process. It looks like Bronx and Jagger were hoping to feel some baby kicks in this throwback snap from when Ashlee was expecting Ziggy.
Loving Looks
Evan and Ashlee have been together for almost a decade and are definitely in the thick of the heavy-duty parenting years. But this red carpet photo from 2020 caught a loving look from Ashlee that makes a pretty strong case that they are still hot for each other and not just "mom" and "dad."
Black & White Magic
There is just something so timeless about this black and white image of Evan and Jagger. The photo, which was taken by Ashlee, is such a perfect capture of the sweetness of the daddy-daughter relationship. We suspect Ashlee will love this picture even more as Jagger grows out of the hand-holding phase.
