25 Times Jackson Roloff Proved to Be the Cutest Kid Ever

25 Times Jackson Roloff Proved to Be the Cutest Kid Ever

Jackson Roloff

It's so hard not to fall in love with this kid! Jackson Roloff is not only an adorable 2-year-old, but has a fun-loving spirit that radiates through any photo his proud mama, Tori Roloff -- or anyone else from the Little People, Big World clan -- snaps of him. He's such a cutie pie and always looks like he's having the time of his life on his assortment of adventures. It gives us major baby fever. Ever since Jackson came into this world on May 12, 2017, he's touched our hearts and made us melt in a way that only this little reality star can.

He's so perfect and just the cutest thing ever!

Even though Jackson has only graced us with his presence for a couple of years, it's been quite the ride -- packed with tons of family escapades that are pretty much #goals. Little J can live it up on the beach, at the zoo, or one of the happiest places on Earth: Disneyland. (Anyone who follows Tori on social media knows she loves that place!)

And when he's not hitting up near and far locales, Jackson enjoys time on his family farm, giving his grandpa Matt Roloff a run for his money.

Jackson might not be the only Roloff tot in the group (his cousin, Ember Roloff, does give him some stiff competition in the cuteness department, and so does his little sister, Lilah Roloff), but he will forever have a special place in our hearts.

Without further ado, here's a look at some of Jackson Roloff's cutest moments so far. Zach and Tori really hit the jackpot with their little guy who continues to make us swoon.
  • Newborn Adorableness


    Little People, Big World cameras documented Jackson's grand debut. As soon as he was born, it was easy to see how much of an adorable charmer this little guy would quickly become, and it was clear that his mom and dad were in love with him from the very first moment.

    Tori and Zach might not be on the show anymore, but at least they'll have these memories with Jackson captured forever.

  • Magazine Official


    We'll never forget squeeing (is that a word, LOL?) over Zach, Tori, and Jackson's photo shoot for People. Just look how cuddly Jackson is! Not every baby gets to appear in a magazine as soon as they've been born, but Jackson's just famous like that -- and given how high profile his family is, this is probably something he should get used to.

    These photos were definitely framers! 

  • Nap Face


    As anyone who follows the Roloffs online knows, Jackson isn't afraid to let folks see how he feels... even when he's feeling a little tired for the activity at hand. "I was apparently boring baby J at our pool day today," Tori wrote in this cute Instagram post. He might have been bored, yes, but we have a feeling that these days, he's way more into spending a day at the pool, like most kiddos are.

  • Bowtie Boy


    Someone was dressed to the nines in honor of Ember Roloff's arrival into the world -- after all, it's important to make a good first impression. "Today we got to celebrate Cousin Roloff! We can't wait to meet you baby girl!" Tori wrote in this post.

    And as always, we love Jackson's look. And that first impression must have been a good one, because he and Ember seem to be total BFFs.

  • Shady Man


    Face it: Babies who rock their parents' shades are guaranteed to make someone swoon over them. It's just the rule! And Jackson is definitely no exception to the rule. Is it just us, or does he look even cooler than most babies while wearing sunglasses? It also helps that his Mickey Mouse onesie is just too cute, so basically, he's just killing it in this outfit as a whole.

  • Family Photo


    There aren't enough words to express how wonderful this Roloff family pic is. "We will treasure these photos forever!" Tori gushed on Instagram. This family is usually pretty photogenic (especially now that they've added daughter Lilah into the mix), but this photo has to be one of our all time favorites. Like the other pics we've seen so far, this one is definitely a framer, too.

  • The Cutest Pumpkin Around


    How can anyone deny an adorable little pumpkin? It seems to be the law that all babies have to dress up as a pumpkin at least once in their lives, and he fulfilled his commitment to that particular tradition in the sweetest way. Jackson definitely was the cutest pumpkin around to celebrate fall at Roloff Farm. What a way to celebrate his first Halloween! It's hard to believe that he was ever that tiny. 

  • Santa's Little Helper


    Mama Tori had no shame plugging Matt Roloff's book, Little Lucy Big Race, during the holiday season with an adorable photo of Jackson in a Santa hat. First of all, it makes sense to support the fam, and when there's a baby around who just so happens to be this cute, it's hard to deny that there would be any better way to sell that book than by using his adorableness to appeal to potential customers.

    Who could say no to this face?!

  • Staying Fresh


    Jackson is one cool kid who likes to stay fresh. Of course he's going to adjust his gear to make hearts everywhere gush.

    Between this and the sunglasses photo, it looks like his mama is raising one cool kid. After all, only cool babies wear their hats backwards, and Jackson definitely seems to have that part down. Watch out, Tori and Zach. This one might end up becoming a bit of a bad boy in the future.

  • Ready for His Close-Up


    Yup, this one definitely does not need any explanation. Jackson is one of the cutest cutie pies around -- and this casual portrait is proof of that. Who could get enough of that smile?! He's been a handsome guy since day one, especially when he's wearing an outfit that's all about the farm life... and considering the family business, we can't imagine him wearing anything else.

  • Getting 'Business' Done


    Back in February, Tori shared this hilarious video of Jackson "taking care of business" while she was trying to have a conversation with him. He might not have thought it was funny, but we sure do, and it seems like his mom felt the same way.

    "You can see Jackson’s enthusiasm for Valentine’s Day," Tori wrote in her caption. "He’s more concerned about his own business."

  • Denim Dude


    Seriously, we can't with this pic -- it's too cute! Jackson looked so stylish during his first snow experience. Given that the Roloffs are based in Oregon, he better get used to plenty of snow and cold winters that are to come, but he looks pretty prepared to us. As Tori explained in her caption, there wasn't a ton of snow to play with, but there's plenty of time for that as Jackson gets older.

  • Snow Baby


    Speaking of snow, Tori's photo of Jackson looking all sorts of cuddly is too much to handle. "Okay I'm dead. If this doesn't break the Internet I don't know what will," the Roloff mom wrote in her Instagram post. "We are so blessed by this friend. God is soooooo good. How he thought we deserve this fella is something I will never comprehend. Love you so much mister."

  • 'Sooo Over It'


    Remember when we said Jackson has no problem letting folks know how he feels by his facial expressions? Yeah, he's a pro. But how many other babies are this cute? That's what we thought. He seems like he's totally over whatever's going on here, and he is not afraid to show it. Once Jackson's older, we have a feeling he's going to be one of those kids who always very candidly speaks their minds.

  • Mister Big Boy


    Jackson is one happy little dude and isn't afraid to show off his pearly whites (OK, mostly his gums) at any and almost every moment. The older he's gotten, the more toothy his smile has become, and it's just as cute as it was here. This is such a cute photo that Tori shared in honor of Jackson turning one! 

    "I now know what all those moms were saying when they said 'it flies by.' This year has done just that," Tori wrote.

  • 'Barefoot Bubbles'


    One of the perks of having such a wonderful and happy child is for said wonderful and happy child to be a source of joy during difficult days, and it seems like Jackson has certainly done that for his mom. "Even when things get a little tough ... this little man reminds me what is important in life: summer blue eyed Barefoot bubbles in the grass," Tori wrote in this touching post.

  • Mama's Boy


    These. Two. Are. Truly. The. Cutest. And somehow, every photo they've taken since has been just as adorable as this one.

    Tori and Jackson Roloff look like one adorable pair in this sweet mother-son snap. Their happiness radiates from the photo and shows how close they are. Hopefully, that bond will never change, not that we think that it will, of course -- we know how much this kiddo loves his mama.

  • Poolside


    This photo of Jackson hanging out along the pool had Little People, Big World fans sounding off in the best of ways. A number of peeps couldn't help but point out how much of a "precious [and] handsome little man" he is -- and we couldn't agree more! Not only does he have his snacks in hand (a pool day must), but he's also all ready with his hat to shield himself from the sun. A total pro!

  • Mommy's 'Heart'


    "You are literally my heart walking around outside of my body. I always say I couldn't love you more and then it happens. I do. I love you baby j," Tori Roloff noted in this heartwarming Instagram post.

    And looking at this photo of Jackson, it's so easy to see why she feels this way about him. All babies are cute, of course, but Jackson's hitting it out of the ballpark with these pics.

  • Daddy's Helper


    There are tons of adorable pic of Jackson, but this one might take the cake -- or in this case, the monkey wrench. Jackson is definitely his father's helper as the duo saved the day when a plumbing issue arose. Teamwork makes the dream work, and that seems to be something these two have figured out. We know they'll continue to make a great team as Jackson gets older and can help his dad out even more! 

  • Mother & Son


    Jackson got in on it when his mom took her maternity photos while she was still pregnant with his little sis, Lilah. It seems like he was ready to be a big brother long before Lilah was even born... and he and his mama look so happy together here. That smile on his face is too cute. If only he'd known at that time all the love and fun that was in store for him as soon as he became a big brother! 

  • Hanging With His Cousin


    It seems like since day one, Jackson and his cousin, Ember, have been thick as thieves, and this photo proves it. We love Ember's arm around Jackson like this -- and now that Lilah's here and Ember has a baby brother of her own, we have a feeling that this group of cousin BFFs is only going to grow.

    "So thankful for this cousin love," Tori wrote in her caption.

  • Looking Dapper


    It's hard to imagine any kid looking as precious as Jackson does, dressed to the nines! Tori also used this photo as an opportunity to reflect on her final months as a mom of one -- it sounds like she appreciated the time it was just her and Jackson more than anything. 

    "It makes me sad to think that our days of just being with Jackson are coming to an end but I’m so excited for our next chapter," she wrote. "He already shows his sister so much kindness by kissing my belly and constantly wanting to hang in her room. It gets me all emotional when I look at this photo and I can hardly see my baby boy any more- instead a confident kid has taken his place." 

  • The Cutest Buzz Lightyear


    is it just us, or is this costume absolutely adorable on Jackson?! According to the caption, though, he just wasn't feeling it. Tori even wrote that even though Buzz is his favorite Toy Story character, he didn't like wearing his costume, but we'd never know it by seeing how cute (and happy) he looks in this photo! Maybe he'll be more into the idea of Halloween costumes next year, when he's a little bit older.

  • Brother & Sister


    Ever since Lilah was born in November 2019, she and Jackson have been inseparable. From all the photos that Tori has posted, it's clear that they look so much alike already -- and he's killing it at being a big brother already.

    This little guy is just too cute, and we can't wait to watch him continue to grow, especially now that he has his sister at his side to experience life with.

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