Jill Duggar Just Got Real About How 'Wrong' It Felt When She First Started Wearing Pants In Public

Jill Duggar Dillard and Derick Dillard on Shiny Happy People: Dillard Family Secrets.
(Image credit: Amazon Prime Video)

The conservative lifestyle portrayed by the Duggar family on their TLC reality show 19 Kids and Counting has always been a fascinating aspect for their fans. It’s been particularly interesting over the past couple of years to see Jim Bob and Michelle Duggar’s daughters start to branch out and shed some of the rules they had growing up in regards to their hair and clothes. Jill Duggar Dillard’s decision to start wearing pants — as opposed to the long skirts she had worn all of her life — was highly publicized, and she has opened up about how “wrong” it felt at first. 

Jill Duggar Dillard and some of her family members, including sisters Jinger, Jessa, and Joy-Anna and even their mom Michelle, have relaxed their views on what is considered “modest” dress in recent years, but that doesn’t mean making the change was easy. In her new tell-all memoir Counting the Cost, Jill opened up about the day she chose to wear leggings to a theme park, writing (via HollywoodLife): 

I’d decided that this was the day that I would first wear pants, but now that I had them on, I just felt wrong.

It’s hard for some to imagine why wearing pants is such a big deal — especially since some family members have since integrated shorts and even swimwear into their wardrobes — but with 32-year-old Jill Duggar Dillard and her siblings growing up under the teachings of the Institute in Basic Life Principles, they were accustomed to avoiding “low-cut, cleavage showing” tops and wearing skirts that fell “below the knee.” in Growing Up Duggar, Jill and her sisters wrote that they, “try to be careful not to wear clothes that are too tight or draw attention to the wrong places.”

Jill Duggar Dillard also knew that her fashion choice that day at the park would not go over well with Jim Bob Duggar, and in Counting the Cost she divulged that her father had made her feel guilty about wearing pants and not discussing it with her parents first. After the meeting with her dad, Jill said: 

I cried when I got home. I felt embarrassed, humiliated, even though nobody else had been in the room with us.

That sounds like a really hard decision that Jill Duggar Dillard made for herself, and in previously speaking about why she chose to start wearing pants, she insists she wasn’t being reactionary, but rather her actions resulted from a re-evaluation of her teachings. Jill said she believed she could still dress modestly while wearing pants. 

Joy-Anna Duggar came to the same conclusion earlier this year, as she followed in some of her sisters’ footsteps by adding pants to her wardrobe. The 25-year-old said that she and her husband had prayed about the issue for a long time, and after reading about “modesty” in the Bible, rather than a black-and-white edict about what one should wear, Joy-Anna decided that she could maintain a modest style even while wearing pants.

Jill Duggar Dillard’s memoir Counting the Cost — which the family has been uncharacteristically quiet about — is now available, and it comes just after the release of the Shiny Happy People: Duggar Family Secrets, which looks at the IBLP teachings followed by the family, as well as Josh Duggar’s troubling past of molestation and child pornography, for which he was sentenced to 151 months in prison. The docuseries can be streamed with an Amazon Prime subscription

Heidi Venable
Content Producer

Heidi Venable is a Content Producer for CinemaBlend, a mom of two and a hard-core '90s kid. She started freelancing for CinemaBlend in 2020 and officially came on board in 2021. Her job entails writing news stories and TV reactions from some of her favorite prime-time shows like Grey's Anatomy and The Bachelor. She graduated from Louisiana Tech University with a degree in Journalism and worked in the newspaper industry for almost two decades in multiple roles including Sports Editor, Page Designer and Online Editor. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.