Fit for the Crown: McLean sisters find fun competing in pageants

Sep. 26—Sisters Rainy and Sky Willoughby of Rumsey are active students at McLean County High School and Calhoun Elementary School, respectively.

But early on in their lives, Rainy and Sky Willoughby — 15 and 7 years old, respectively — have made a name for themselves in the competitive pageant world via their mother Tammy Willoughby's interest.

"My mom always took me to the McLean County Fair Pageant every year," Tammy Willoughby said. "Way back when, it was at Calhoun School, and the fair was a huge deal then, and in the gym — each night they would have the 'Little Miss' pageant or 'Miss McLean County' pageant ... and we would always go and watch it."

Tammy Willoughby enrolled Rainy Willoughby into her first pageant at about 1 year old for a Tiny Tot pageant, and she won her first competition the following year.

"That's what we call the 'pageant bug' ... when she won," Tammy Willoughby said. "We were kind of just hooked after that."

Sky Willoughby's first win came when she was three weeks old.

"She was bald headed and won 'Best Hair,' " Tammy Willoughby laughed. "It was the bow."

Rainy Willoughby's earliest memories of beginning to compete and becoming enthusiastic was when she would travel to smaller pageants.

"I would get excited, even if I just won something small or little because the prizes weren't as big at these pageants compared to the ones I do now," she said. "I do remember getting so excited, even if it was for 'Best Smile' or something like that."

The competition schedule has increased since Rainy Willoughby began. They originally started out making appearances at pageants every other week when she was younger, before becoming more involved with larger pageant systems.

Rainy Willoughby competed many weekends at county fairs this year in order to get her shot at the 2022 Miss Teen Kentucky County Fair Pageant in October.

"That's pretty much been my entire year — to make it to the state pageant," she said.

"In Kentucky, (the) county fair is a big deal. It's like the Kentucky version of 'Miss America,' " Tammy Willoughby said. "...These pageant girls spend all summer traveling around Kentucky ... and hoping to get that bid to go to state."

Rainy Willoughby was able to secure a spot after winning the Miss Teen title at the Crittenden County Fair in July, marking her fifth time making it.

Sky Willoughby ended up winning the Little Miss title for Henderson County and already made the trip on the first day of the Kentucky State Fair in August for her first time.

"I had a lot of fun," Sky Willoughby said. "I was kind of sad when I didn't win, but I had fun."

Rainy Willoughby's appearance at the state fair in the pre-teen division in 2019 saw her win 1st Runner Up, which is the highest title that anybody's held representing McLean County, according to Tammy Willoughby.

One of the portions of the competition is mastering the walk, which sometimes can take "many hours."

"It's just (about) getting it down where you don't look uncomfortable on stage," Rainy Willoughby said. "When you go on stage — you need to look like you are confident, you know what you are doing, you own this room and I am getting the crown."

But Rainy Willoughby said the most important facet is the interview portion — which accounts for about 50% of the judging criteria.

"I know that I have had (struggles) with the interview (portion)," Rainy Willoughby said. "Preparing for that is the hardest because when you go into a room, you don't know who you're talking to, but then they ask you all these questions, and it's nerve wracking because you know they're judging what you're saying.

"For me, preparing is learning to talk to people, learning to be comfortable with what I'm going to say and being quick and being able to answer a question (well)."

For Sky Willoughby, the interview portion is a little bit simpler, but she is in the process of transitioning into more formal questioning to compete in pre-teen division next year, according to Tammy Willoughby.

While trying to win is the overall goal, Rainy Willoughby's found another purpose in the pageant world, particularly being able to emphasize the importance of mental health, which she and family members have struggled with.

"For me, pageants are really about being able to share what I believe in and what is important to me," Rainy Willoughby said. "I know I started with (seeing it) as something to do, but it really has become a way to spread awareness of my passion and my platform."