The Jerry Ann Taylor Best Dressed Award: Where Cowgirl and Fashionista Meet

The Jerry Ann Taylor Best Dressed Award is a coveted honor and comes with a substantial cash prize, recognizing the cowgirls who put a little extra flair into their outfits

Teal Stoll | Nov 2, 2024

Fallon Taylor, three-time Jerry Ann Taylor Best Dressed Award winner and creator/owner of Ranch Dressn / Black Bird Media

In the roots of rodeo, flashy-dressed women on fast horses were a sort of sideshow attraction in the early days of organized competition. They may not have won any money, or very little, but they wore fun outfits and thrilled the crowds as they took their turns at top speed. As rodeo progressed, women have found their footing and turned the sport into a profession through the Women's Professional Rodeo Association.

One thing that has never changed though, is the love many women have for their outfits. Flamboyance and fun have always been two words that could describe the wardrobe of most barrel racers. Many rodeo fans are familiar with Fallon Taylor or Martha Josey, both World Champions, who love to dress with special flair. The extra sparkle and glamour is a huge attraction for rodeo fans in the barrel racing.

The Jerry Ann Taylor Best Dressed Award is given in honor of the incredible trick rider and Hall of Fame Cowgirl, who was also known for her own fabulous style. After Taylor passed away in 2012, her family created a fund to keep her spirit of fashion alive in rodeo. The award is given twice annually (at the Fort Worth Stock Show and Rodeo and the National Finals Rodeo) and comes with a substantial cash bonus along with a bracelet or plaque.

Fans vote throughout the NFR and last year was a record-breaking year, with over 40,000 combined fan and committee votes. Along with the National Cowgirl Museum and Hall of Fame, the WPRA honors these cowgirls.

Sissy Winn, who now partners with Fallon Taylor's clothing line, Ranch Dressn, has earned the title three of the past four times it was awarded (the Fort Worth Stock Show and Rodeo in 2022 and 2023 and the National Finals Rodeo in 2023). Taylor herself has earned the award three times.

Here is a full list of the winners over the years:

2012 NFR: Mary Walker
2013 FWSSR: Kendra Dickson
2013 NFR: Fallon Taylor
2014 FWSSR: Jane Melby
2014 NFR: Fallon Taylor
2015 FWSSR: Kendra Dickson
2015 NFR: Fallon Taylor
2016 FWSSR: Shelly Anzick
2016 NFR: Michele McLeod
2017 FWSSR: Kathy Grimes
2017 NFR: Kimmie Wall
2018 FWSSR: Sadye Simpson
2018 NFR: Jessica Routier
2019 FWSSR: Stevi Hillman
2019 NFR: Jessica Routier
2020 FWSSR: Jimmie Smith
2020 NFR: Tiany Schuster
2021 NFR: Molly Otto
2022 FWSSR: Sissy Winn
2022 NFR: Margo Crowther
2023 FWSSR: Sissy Winn
2023 NFR: Sissy Winn

Who will take home the title in 2024? It will be fun to see, especially with multiple top cowgirls again dressed in Fallon Taylor's brand - which always seems to be a crowd favorite.

Published Nov 2, 2024

TEAL STOLL

Teal Stoll is a lifelong Wyomingite from a working ranch family of several generations. Both sides of her family have deep roots in rodeo, as contestants and stock contractors. Teal grew up horseback and actively competes in rodeos and barrel races. She has degrees in both business and accounting, which she uses operating her own bookkeeping service. Teal enjoys spending time with her horses, training colts, and maintaining her string of athletes. When she isn’t at the barn, she can be found reading, doing yoga, or on her paddle board at the lake. Teal lives with her fiancee and a plethora of animals, because she can’t say no to a displaced critter with a sad story. When she isn’t on the road running barrels, she spends her time helping with day to day operations on the family ranch.