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Miss GayDays® 2025 Kolbie Blair'e Matthews

From the small-town roots of Grafton, WV, to the sun-drenched stages of Jacksonville, FL, the journey of Kolbie Blair’e Matthews is one of glitter, grit, and transformation.

Born the "odd ball" of seven, Kolbie moved to Florida in 2005 at age 14. Coming out at 16, they never imagined a life defined by the power of a pair of heels. However, 16 years ago, the "wow factor" of the stage—the transformative magic of makeup and the magnetic confidence of drag entertainers—captured Kolbie’s heart and never let go.

The debut performance took place at the legendary Bo’s Coral Reef in Jacksonville. Despite the nerves of the unknown, Kolbie performed with a determination that quickly secured cast spots at both Bo’s and Metro Entertainment Complex. For 15 years, Kolbie has brought art to life across Florida, Georgia, and Kentucky, fueled by a passion that only intensifies with every spotlight.

For years, Kolbie was "always the bridesmaid," serving as the creative force behind the scenes—creating looks, styling hair, and applying makeup for other pageant contestants. In 2023, Kolbie finally stepped into the competitive ring. After placing First Alternate in a debut newcomer pageant, they captured the crown of Miss Incahoots Newcomer just two days later.

Craving a bigger challenge, Kolbie set their sights on a premiere title. After three pounds of makeup, a pinch of glitter, and zero sleep, the dream became a reality. Today, Kolbie Blair’e Matthews proudly reigns as your Miss GayDays 2025.

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Miss Gay Days
Miss Gay Days

Be a Contestant!

Welcome to the exciting world of GayDays®, the largest Gay & Lesbian Vacation Destination Event! The Miss GayDays® Pageant will be part of the most exciting week of events, expos, and parties. We are excited the 2025 GayDays® Orlando and the Miss GayDays® Pageant are returning to the Doubletree Resort by SeaWorld.

**Prizes for the winner include:

  • $1,200 cash ($400 paid after crowning, $800 paid at the end of contractual obligations)

  • Flight and accommodations for GayDays® Orlando 2025.

  • Flight, accommodations, and booking fee of $125 for additional GayDays® events, prides, and festivals (notice will be provided at least 30 days prior to booking).

Miss GayDays® History

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