I first met Jack Simmons a few years ago.  I was running the annual Trek for the St. Joseph Peach Mission for Children which, at the time, started in downtown Calhoun, Kentucky and went all the way the hilly and arduous KY 815 to West Louisville.  Somewhere along the 13.1 mile route that day, I stopped to get a bottle of water from my friend Kathy Simmons.  She lives out that way and supported the runners, bikers and walkers by setting up a water stop at an intersection of the highway.  On that particular day, her son Jack was with her.  He was in town visiting his family.  Kathy introduced us and we chatted for a few minutes before I had to take my sweaty, ripe, hot mess of runner back to the course.  Shortly thereafter, Jack and I became friends on Facebook and I have been enjoying the ride since.

Jack is the master (or mistress) of mind-blowing, gender-bending fashion and he will walk a runway, rock out a red carpet or the strip in Las Vegas- boldly, loudly and proudly.

But it didn't always used to be that way.  The first time Jack ever threw on a pair of high heels was for his 30th birthday party, which was red-carpet, celebrity-impersonator themed.  He decided to ring in 30 by dressing up as, wait for it, Cher!

Jack Simmons/FB
Jack Simmons/FB
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Jack admits that he was nervous about posting photos from that party on social media.  He was afraid of what his friends and family from Owensboro might think.  As it turns out, the feedback was "amazing."   He says, "I've posted some crazy outfits in thigh high boots and who knows what else, but people have been very supportive."

And while it took Jack a long time to be truly comfortable showing that side of himself, particularly to folks back here in Owensboro, he has thankfully retired that inhibition. I'll own it.  He's one of my favorite Facebook friends.  I'm routinely blown away by his photos and creativity.  He says, "I love a good theme party, or just dressing up for a night out with friends. I f it’s a fun outfit, I will wear it. If it will get a smile or laugh out of people, it makes it worth it."

That brings us to Jack's country queen, Shania!

Jeff Bottari/Getty Images
Jeff Bottari/Getty Images
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Jack has always loved country music and, fun fact, used to always listen to it on WBKR when he lived here in Owensboro. He's in Tampa, Florida now, where he moved after graduating from UK back in 2013.  He says that, back in the day, Shania was always his favorite singer and he and his friend Audra Posey used to listen to all of her albums on repeat. If they were jumping on the trampoline or sledding in the snow, they would cart their CD player outside and blare Shania in the background.  In Jack's words, "We had a Shania concert where ever we were."

Of course, Shania had a bunch of big country hits to sing along to- "Whose Bed Have Your Boots Been Under," "Honey, I'm Home", "You Win My Love" and Jack's personal favorite- "Don't Be Stupid."

And, of course, one of Shania's most iconic videos is the one she filmed for "That Don't Impress Me Much."  You remember this, don't you?

Well, Jack certainly remembers it.  And he just brought it back to life at Shania's concert in Las Vegas. Shania's "Let's Go!" residency is currently underway at Zappos Theatre and Jack had the chance to go see her.  He admits, "We had such a good time, we almost bought tickets the next night to go back and see her again."

But while there's no doubt that Shania was the star of the show, Jack was certainly turning his share of heads too. He decided to pay tribute to Shania in a completely unexpected way. He dressed up like her and staged an absolutely epic and inspired elevator reveal.

Jack says that when his friends Tiffany and Alli said they wanted to go to Vegas to see Shania, he knew instantly he was going to dress up for the show and was doing it in that "iconic Shania look".

So, Jack called his friend Viktoria Sommers, a Tampa-based drag queen who was thrilled to help. Jack made the boots and the hat box. Viktoria sewed the outfit.  Together, they very clearly "nailed" the ensemble!

Tiffany Lawrence/Alli Ducker
Tiffany Lawrence/Alli Ducker
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Jack says he got a few strange looks in Vegas, but, for the most part, people loved it.

Tiffany Lawrence/Alli Ducker
Tiffany Lawrence/Alli Ducker
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He added, "The people giving the funny looks clearly don't know who Shania is."  But most people instantly got the reference and Jack says some tourists on the Vegas strip were even tipping him to take photos with them.

By the way, Jack got some love from his country queen.  Shania saw the photos on Instagram and chimed in!

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I love Jack's willingness to just go for it.  The guy's got style and sense. He says, "Life's no fun if you take it too seriously and can't laugh at yourself along the way."

Tiffany Lawrence/Alli Ducker
Tiffany Lawrence/Alli Ducker
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There's no doubt that his look was a gender-bending master class.  He admits that he even thought about shaving his beard, but decided the beard made his Shania even funnier.  He said, "You see everything in Vegas, so this should be no surprise."

But Jack's full of surprises. He's a master of illusion and I personally can't wait to see what's next.  Cue the elevator door, Jack!  Let's see what you've got up those leopard-print sleeves.

Here's Jack talking about his incredible Shania adventure:

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