'Pioneer Woman' Ree Drummond's Sweetest Family Photos Through the Years

The Food Network star and her family of ranchers share memories and milestones on social media

01 of 28

NYE FAMILY KARAOKE

ree drummond
ree drummond/ instagram

The Food Network star's daughter Alex Drummond Scott shared a series of videos featuring the family together on New Year's Eve. "Ringing in 2022 in my fav place with my fav people!! 💖🤠🌟 bye bye 2021, you were good to us," Alex captioned the post. "P.S. comment if you think we should start a band."

The Pioneer Woman star and her family's karaoke song of choice? "Take It Easy" by The Eagles.

02 of 28

ANNUAL MATCHING PAJAMAS

Ree Drummond Family
Ree Drummond/Instagram

Most of the Drummond family gathered for an adorable shot in snowman-themed PJs. But the Drummond family tradition was just missing one familiar face: daughter Alex, who is spending her first Christmas with husband Mauricio in his hometown of Monterrey, Mexico. Their absence meant the Drummond kids' annual matching pajamas picture wasn't quite complete but gives fans something to look forward to for next year's Christmas at the Drummond's home.

03 of 28

TODD'S QB POSITION

Ree Drummond Instagram
Ree Drummond Instagram

Ree and Ladd are almost empty nesters with four of their children out of the house but their youngest, Todd, is still at home. Having Todd at home is "easy," the Pioneer Woman star told PEOPLE then, though she did say that it meant she and Ladd have "football just coming out of our ears."

"His older brother was QB for three full years, so this was Todd's first season in the starting spot," Ree wrote of Todd, in a caption accompanying a gallery of photos of the high school junior on the field.

04 of 28

25 YEARS OF LOVE

Ree Drummond Instagram
Ree Drummond Instagram

The love between Ladd and Ree has always been adorable but Ree shared a story in an Instagram post about Ladd going above and beyond.

"He not only drove me to Dallas last week for my cookbook signing because he knew I was too pooped to drive myself, he also came to the bookstore to check on me and wound up signing books and taking pics once the signing was over," the Food Network Star wrote. "And when he stopped to fill up on the drive home the next morning, he bought me a Diet Dr Pepper and a string cheese. Find a partner who will drive you and buy you cheese when you need it most, is what I'm saying."

In September 2021, the pair celebrated 25 years of love that "deepens, expands, and becomes more firmly rooted over time," wrote the Pioneer Woman in a caption.

05 of 28

BRYCE GOES OFF TO COLLEGE

Ree Drummond Drops Son off at College
Ree Drummond/ instagram

In January 2021, the first Drummond son to go off to college. The proud mother shared pictures of her eldest son who graduated high school a semester early and will be playing football at the University of North Texas.

06 of 28

JAMAR SIGNS TO PLAY FOOTBALL

Ree Drummond and Ladd
Ree Drummond / instagram

Ree shared her pride in an Instagram post revealing that her teenage foster son has been accepted to the University of Central Oklahoma and is "officially signed to play football" at the school beginning in the fall 2021 semester.

Jamar played on the same high-school football team with Bryce and Todd and all three boys still play football now.

07 of 28

WEDDING FESTIVITIES

Ree Drummond
Alex and Ladd Drummond. Ree Drummond/Instagram

2021 was a year with many highs and lows for the Drummond family. Ladd broke his neck in a frightening truck collision that injured Ladd and their nephew, Caleb. This injury left Ladd in a neck brace.

But Ladd and Caleb were healed and able to enjoy themselves at Alex's wedding. Ladd was even able to take off his brace to walk his daughter down the aisle and to do his first dance with Alex.

08 of 28

LIKE MOTHER LIKE DAUGHTER

Ree Drummond, Paige Drummond
Ree Drummond/Instagram (2)

Paige was not the Drummond daughter who got married in 2021 but she did look the part while trying on Ree's dress! "Paige, you look beautiful even though this was just for fun!" the mom of five gushed in her Instagram caption.

09 of 28

BONUS KID

Ree Drummond family

Meet Jamar, Ree's "bonus son." In an excerpt from her forthcoming book of essays, Frontier Follies, the cook introduced her foster son, Jamar, who has been living on their Oklahoma ranch for the past year and a half. Ree kept Jamar out of the spotlight at first because of state agency restrictions, but now that he is 18, they no longer apply.

"He's larger than life, has a hilarious laugh, and is extremely smart—both book and street. He's a great kid who's overcome some difficulties in his life," she writes. "I'm proud of the kid, and I can't wait to see where life takes him."

10 of 28

HAPPY BIRTHDAY BRYCE

Bryce and Ree Drummond
Ree Drummond/ Instagram

Ree celebrated her oldest son's 18th birthday in September by gushing on social media of course! "Before he was a quarterback, he was a cowboy," wrote the proud mom, sharing throwback photos of Bryce on the family's ranch. "Can't believe he's 18...it went by so ridiculously fast. His dimples are still the death of me. 😂 "

11 of 28

ALEX SAID YES!

Alex Drummond gets engaged, Dree Rummond
Alex Drummond/Instagram; Getty Images

"These two are gonna have so much fun together," Ree wrote after her daughter Alex, 23, became engaged to her new fiancé, Mauricio Scott.

Alex also shared the happy news on own social media, posting sweet photos taken of the moment Mauricio, 23, got down on one knee.

"Still waiting for someone to pinch me??!?!" she wrote alongside the post. "Mauricio Scott is the sweetest picture of God's goodness and provision. And I get to spend FOREVER with him!! I love you, fiancé!!!!!!!"

12 of 28

GRADUATION DAY

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Ree Drummond/Instagram

The culinary star celebrated her daughter Paige's high school graduation during the same weekend as her nephew Caleb's. She shared photos of her kids at both ceremonies, and was sentimental about the entire weekend. "They were all tiny cowboys/cowgirls yesterday! Now they won't stop graduating from high school," she wrote on Instagram. "I asked Bryce and Todd to promise me they will never pursue independence, higher education, or any of that nonsense that would one day take them away from their mother. (They have not gotten back to me yet...)"

13 of 28

FAMILY DINNER

pioneer-woman-family
Ree Drummond/Instagram (2)

During a recent visit to her Pawhuska restaurant and retail store, The Mercantile, Ree ate with her sons Bryce and Todd and their friends on one side and her daughter Paige and her friends on the other. "Ladd and I had a quiet, romantic dinner right in the middle of them. Just kidding on the quiet, romantic part!" she joked on Instagram. "But you know what? It's fun to be surrounded by teenagers."

14 of 28

TIGHT BOND

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Ree Drummond/Instagram

The blogger shared a glimpse into what life on the ranch was really like with little ones. "Todd didn't want to be put down that day," she said of her youngest son, now 13. "Cowboys really only need one arm to work with!"

15 of 28

FIRST-TIME FATHER

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Ree Drummond/Instagram

Throwback! Ree posted this shot of her cattle ranching husband, Ladd, holding their oldest daughter, Alex, as a baby. "One of my favorite photos of all time," she wrote. "Ohhhhhh, the feelings this evokes."

16 of 28

LITTLE RANCHERS

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Ree Drummond/Instagram

"My two girls and my two nephews at the Lodge in the year 2000. They always wore pajamas in those days---heck, this was probably 3:00 in the afternoon. Also, there's no telling what Paige is eating," wrote Ree.

17 of 28

COUNTRY COWGIRL

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Ree Drummond/Instagram

Ree reflected on this day in 2011 when she pretended she was going to rope the dummy steer but then turned and snagged Ladd instead. "It's how we show affection out here in the country," she joked.

18 of 28

DRIVING WITH THE POOCH

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Ree Drummond/Instagram

Ree's love for her animals knows no bounds, and here she is with her beloved late bassett hound, Charlie, in 2015. "Me and my buddy! He's thrilled to be here," she captioned.

19 of 28

SELFIE SUNDAY

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Ree Drummond/Instagram

"I've been trying to come up with a clever caption for our family Easter photo," Drummond captioned this sweet shot in 2016. "How about 'Salvation Selfie?' (Sorry. Ha.)"

20 of 28

TENDER MOMENT

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Ree Drummond/Instagram

"Smoochie Selfie. Actually, we'd been dancing to 'Love Shack' and were really sweaty, so I guess I should call it Sweaty Smoochie Selfie," Ree captioned. "Weddings are fun for an old married couple like us!"

21 of 28

GRADUATION DAY

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Ree Drummond/Instagram

Ree was understandably emotional at Alex's high school graduation in 2015. "She's a graduate! This is before the ceremony. DURING the ceremony, when it was our turn to get on stage and speak to our child, I cried and passed my husband the mic, then he cried and passed me the mic," she wrote. "We are not handling this well. But the rest of the ceremony was just dandy! Ha."

22 of 28

SUMMER VACATION

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Ree Drummond/Instagram

In their go-to vacation destination of Vail, Colorado, Ladd convinced Ree to embrace her adventurous side. "We've had a wonderful family trip this week and today's our last day!," she captioned this sweet shot. "To go out with a bang, this guy is making me do some zip-line thing over a huge canyon. Hold me."

23 of 28

CATTLE RANCHERS IN THE CITY

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Ree Drummond/Instagram

While visiting the Big Apple for the launch of her lifestyle magazine, the family caught the popular Broadway show Hamilton. "It was beautiful. Brilliant, touching, poignant, and real. I cried three times. Okay, four. Then we got lost on the subway getting back to our hotel. A memorable ending to our New York trip!," said Ree.

24 of 28

SWEET SISTERS

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Ree Drummond/Instagram

Visiting Alex at college in Texas, Ree and her other daughter Paige got to be there for a special moment. "Paige and I went to Alex's sorority bid day this weekend and it was so much fun to get some more hugs in," Ree captioned. "Also, it was precious for me to see that Alex has found a group who will be there for her and have her back as she navigates this new phase in her life."

25 of 28

FRIDAY NIGHT LIGHTS

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Ree Drummond/Instagram

For her son Bryce's last high school football game of the season in 2017, the family was there to show their support. "Paige and my mom were there cheering him on (and keeping each other warm.)," wrote Ree.

26 of 28

MOTHERLY LOVE

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Ree Drummond/Instagram

"I wanted to state for the record that I L❤️VE this child and think he's pretty neat. Yep...I'm a Todd fan," she captioned on this sweet shot with her youngest son in December 2017.

27 of 28

GROWING UP SO FAST

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Ree Drummond/Instagram

"Next time Alex comes home from college and her 'little' brother says he can lift her up on his shoulders...she will believe him," Ree captioned this Instagram photo. "Also, my children are now nine million years old and forty trillion feet tall. Goodbye."

28 of 28

CHRISTMAS TRADITION

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Ree Drummond/Instagram

"We all get matching pajamas late on Christmas Eve," Ree recently told PEOPLE. "The dogs get them too!"

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