Jessa Duggar's Style Evolution: See How Her Look Has Changed

Jessa Duggar's Style Evolution: See How Her Look Has Changed

As a mom of four, Jessa Seewad (née Duggar)’s style is all about keeping up with her busy lifestyle. But how has it changed over the years? Back in the day, all the Duggars used to wear matching outfits and conservative, school-girl style dresses. But ever since the Counting On alum started picking her own outfits as she’s grown into adulthood, she’s had a distinct sense of style. Graduating from casual long skirts and dresses, the star has learned how to add a little sparkle to her low-key looks.
While Jessa has experimented with louder patterns and a little bit of edge, comfort is still key when it comes to her wardrobe. Following the birth of her daughter Ivy Jane in 2019, she was thrilled to do away with her maternity clothes and have fun with fall fashion.Jessa Duggar's Style Evolution: See How Her Look Has Changed

“Seriously, [these are] some of the cutest, most comfy dresses,” she said on Instagram as she tried on outfits at the Bates Sisters Boutique in September 2019.  “Literally everything that I’m trying on, I just cannot believe how well I love the fit. [They’re] super comfy. Just absolutely adorable things. … This is a denim skirt that you just want to live in. It’s super stretchy, comfy, perfect length. I love it. And the momma bear shirt. How fun!”
It looks like Jessa’s oldest daughter already has an interest in fashion like her mom. “Ivy, what do you think? You like it?” she asked, modeling an outfit for her daughter. “Yeah! She says, ‘Make one in my size.’”

In addition to Ivy, Jessa and her husband, Ben Seewald, also share sons Spurgeon and Henry and daughter Fern.Jessa Duggar's Style Evolution: See How Her Look Has Changed

The Duggar girls previously explained their strict dress code enforced by their parents in their 2014 book, Growing Up Duggar. “We do not dress modestly because we are ashamed of the body God has given us; quite the contrary. We realize that our body is a special gift from God and that He intends for it to be shared only with our future husband.”
Now that Jessa has gotten older, we love that she is branching out and trying new things.
Check out the gallery below to see how her style has evolved over the years. 

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We love those heeled booties … a rare thing for her!”,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2020\/11\/ben_seewald_123270997_730645097809059_5445368773973728288_n.jpg?resize=1080%2C1200&quality=86&strip=all”,”width”:”1200″,”height”:”1200″},{“@type”:”ImageObject”,”datePublished”:”2021-03-17T16:01:41-04:00″,”caption”:”There was a time when Jessa would never be spotted in a dress above her knees, but she’s come a long way.”,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2020\/11\/jessaseewald_115833331_165142735143650_2093433768956317230_n.jpg?resize=1080%2C1200&quality=86&strip=all”,”width”:”1200″,”height”:”1200″},{“@type”:”ImageObject”,”datePublished”:”2021-03-17T16:01:42-04:00″,”caption”:”The Duggars don’t wear traditional swimsuits, but Jessa looked adorable at the beach in this form-fitting blue dress.”,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2020\/11\/jessa.jpeg?resize=469%2C628&quality=86&strip=all”,”width”:”1200″,”height”:”1200″},{“@type”:”ImageObject”,”datePublished”:”2022-07-21T16:03:41-04:00″,”caption”:”Jessa wore a tight floral dress while posing for a photo with her mom,\u00a0Michelle, and sister,\u00a0Jana,\u00a0in July 2021.”,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2021\/08\/Tight-Dresses.jpg?resize=1080%2C1200&quality=86&strip=all”,”width”:”1200″,”height”:”1200″},{“@type”:”ImageObject”,”datePublished”:”2022-07-21T16:03:41-04:00″,”caption”:”She rocked a classic denim skirt while attending a conference in October 2021.”,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2021\/08\/Denim-Skirts.jpg?resize=1200%2C1200&quality=86&strip=all”,”width”:”1200″,”height”:”1200″},{“@type”:”ImageObject”,”datePublished”:”2022-07-21T16:03:41-04:00″,”caption”:”The mother of four had an\u00a0outfit change\u00a0at the conference, choosing to rock a flowy black dress and yellow cardigan.”,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2021\/08\/outfit-change.jpg?resize=1200%2C1200&quality=86&strip=all”,”width”:”1200″,”height”:”1200″},{“@type”:”ImageObject”,”datePublished”:”2022-07-21T16:03:41-04:00″,”caption”:”Jessa knows how to have fun with her style. In February 2022, the reality star showed off her family\u2019s outfits for their\u00a0fourth annual \u201cDuggar Family Ugly Sweater Party.\u201d”,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2021\/08\/Jessa-Ugly-Sweater.png?resize=714%2C406&quality=86&strip=all”,”width”:”1200″,”height”:”1200″},{“@type”:”ImageObject”,”datePublished”:”2022-10-26T10:03:58-04:00″,”caption”:”Jessa looked modern and stylish in black pants \u2014 a rarity for the TLC alum.”,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2022\/07\/275691626_353832309993017_763989786764705306_n-1.jpg?resize=1080%2C1200&quality=86&strip=all”,”width”:”1200″,”height”:”1200″},{“@type”:”ImageObject”,”datePublished”:”2022-11-21T14:39:27-05:00″,”caption”:”Ringing in her 30th birthday in November 2022, Jessa took to Instagram to share a message with fans about the milestone. \u201cI don\u2019t know what I was expecting, but 30 really feels no different [than] 29 to me,\u201d she admitted. \u201cLast year\u2019s 29 definitely felt like my big milestone birthday of the decade. And 30 is awesome!\u201d And while Jessa\u2019s celebratory donuts took center stage, she sported a super cute, very Duggar-rebellious outfit of black ripped skinny jeans, black boots and a tan shacket. “,”url”:”https:\/\/www.intouchweekly.com\/wp-content\/uploads\/2022\/10\/Jessa-Duggar-Style.jpg?resize=1080%2C1200&quality=86&strip=all”,”width”:”1200″,”height”:”1200″}]}
1 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Ben Seewald/Instagram

Duggar Statement Headbands

Jessa was all about the big headband back in the day. Though she hasn’t held onto the trend like big sister Jill Dillard (née Duggar) has, she knew how to work the look back in the day.

2 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Ben Seewald/Instagram

Wind-Swept Waves

Of course, having her hair pulled back isn’t exactly Jessa’s signature look. She’s more well known for her long, carefully-curled locks. The busy mom has some of the best hair in the fam.

3 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Color Coordinated

Feeling green! To make sure the outfit was modest enough, Jessa also wore a plain white top underneath, something she frequently pairs with her looks.

4 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Hats Off

We’re tipping our hats to the star’s choice of accessories. When she and husband Ben spent time in the snow, she made sure to pick something fuzzy and warm.

5 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Comfy Casual

The Duggars don’t really do bathing suits the way the rest of us do, so when the star hit the beach, she kept it covered up but casual in a red-and-black plaid shirt that matched her man’s ensemble.

6 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

All Dressed Up

When Jessa and Ben were on their honeymoon in Italy, they even stopped by a hat store to pick up some out-there accessories. The one Jessa chose matched her outfit flawlessly.

7 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Bump Beauty

Jessa’s style hasn’t change too much over the years, but when she got pregnant for the first time, she definitely put an emphasis on comfort. Her wardrobe was all about flowy skirts and soft tops.

8 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Sporty Sweetie

Every now and then, she also mixed in some sporty looks, like this football jersey-themed top. Considering Jessa and Ben’s joint bachelor/bachelorette party was a football game, it feels totally on brand for the star, too.

9 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Team Pride

Jessa also occasionally mixes in some swag for the University of Arkansas Razorbacks. Though neither she nor her hubby went to the college, the family has adopted the hogs as their own.

10 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Pop of Color

While pregnant, Jessa also worked in this bright yellow cardigan. It’s an article of clothing that seems to make the rounds a lot between the Duggar sisters, especially when they’re expecting.

11 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Bangs Alert

It’s hard to tell from social media, but there was actually a brief period of time where Jessa experimented with her hair, trying out front bangs. Though it wasn’t long before she started sweeping them to the side and pinning them back, we love that she tried something new.

12 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Ben Seewald/Instagram

Full Fringe

During that time, Jessa even gave her bangs a code name — Molly — so that she could discreetly ask her sisters and friends how her hair looked while they were out in public.

13 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Mom on the Go

Now that she’s a mom of four, Jessa has kept her cozy look going, though she’s learned how to make things look polished when she’s on the run. Instead of just pairing any tee with a skirt, she’s stuck to a more muted color palette with simple details.

14 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Cousin Couture

She’s also been shopping at cousin Amy Duggar‘s new boutique, 3130 Clothing. The star has tried on cool shirt-dresses from the store.

15 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Accessories A-Go-Go

Jessa brought her hat habit back to jazz up a simple outfit while pregnant with baby No. 3, Ivy. Now that she’s got (two!) daughters, we can’t wait to see her really step up her style game as she picks out all kinds of adorable little outfits for them.

16 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Learning From Her Sister

It looks like Jessa is taking notes from her sister Jinger Duggar, who has developed a reputation for taking fashion risks. The two smiled big in a December 2019 photo as they rocked funky coats.

17 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Dressing Up for Date Night

Jessa even sported a fun jacket during a date night with Ben — even though they only went to the supermarket!

18 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Matchy Matchy

The proud mama can’t help but match her adorable baby girl. “I’m not a mom who usually dresses my kids alike or does a whole lot of the ‘matching’ thing,” she wrote on Instagram about Ivy. “Baby girl, this time I just couldn’t resist.”

19 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy Jessa Duggar/Instagram

Fashionistas in the Making

When she gathered with her sisters, Jessa opted to wear a simple, yet classic black number.

20 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy Jessa Duggar/Instagram

Sunday Best

Jessa rocked a button-up frock for her Sunday church visit with Ben and their three kids prior to baby Fern‘s birth.

21 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy Jessa Duggar/Instagram

Details, Details!

The TV personality gave a closer look at her custard-colored midi-dress in another portrait.

22 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy Duggar Family/Instagram

Exciting Occasion

The TLC mama kept cozy while reuniting with several of her loved ones for a baby shower.

23 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy Duggar Family/Instagram

Picture-Perfect

Jessa wore a casual green and black striped-dress for the special occasion.

24 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Ben Seewald/Instagram

Birthday Queen

Ben shared this photo while celebrating Jessa’s birthday in November 2020, and she definitely got glammed up for their date night! We love those heeled booties … a rare thing for her!

25 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Knees!

There was a time when Jessa would never be spotted in a dress above her knees, but she’s come a long way.

26 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Chic and Comfy

The Duggars don’t wear traditional swimsuits, but Jessa looked adorable at the beach in this form-fitting blue dress.

27 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Tight Dress

Jessa wore a tight floral dress while posing for a photo with her mom, Michelle, and sister, Jana, in July 2021.

28 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Denim Skirts

She rocked a classic denim skirt while attending a conference in October 2021.

29 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Outfit Change

The mother of four had an outfit change at the conference, choosing to rock a flowy black dress and yellow cardigan.

30 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Duggar/Instagram

Ugly Sweaters

Jessa knows how to have fun with her style. In February 2022, the reality star showed off her family’s outfits for their fourth annual “Duggar Family Ugly Sweater Party.”

31 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedJessa Duggar/Instagram

Rare Look

Jessa looked modern and stylish in black pants — a rarity for the TLC alum.

32 of 33Jessa Duggar's Style Evolution: See How Her Look Has ChangedCourtesy of Jessa Seewald/Instagram

Dirty 30!

Ringing in her 30th birthday in November 2022, Jessa took to Instagram to share a message with fans about the milestone. “I don’t know what I was expecting, but 30 really feels no different [than] 29 to me,” she admitted. “Last year’s 29 definitely felt like my big milestone birthday of the decade. And 30 is awesome!” And while Jessa’s celebratory donuts took center stage, she sported a super cute, very Duggar-rebellious outfit of black ripped skinny jeans, black boots and a tan shacket.

33 of 33

A Doll!

Jessa and Ben’s daughter Ivy is precious — watch the video above to see her cutest moments.