If The Shoe Fits: Key West National Finals

 Saturday, October 10, 2026 at 8:00 PM. The national finals of If The Shoe Fits land in Key West, outside the Bourbon Street Pub and New Orleans House at 724 Duval Street, and the winner earns one of the island's most coveted titles.

Regional winners from Dallas, New York, Minneapolis, West Hollywood, Jacksonville and Wilton Manors compete across three categories: Opening Presentation, Talent Showcase and the CNN Couture Interview. The national champion takes home a $2,000 performance fee, along with accommodations, airfare and a custom costume.

The real prize is the crown. The winner becomes Queen of New Year's Eve and descends in the iconic red high heel during the countdown to midnight at the 29th annual Key West High Heel Shoe Drop on Thursday, December 31.

There is no cover charge, though attendance requires an RSVP on Eventbrite. The event is 21 and up.

If The Shoe Fits is produced by Bourbon Street Pub in partnership with New Orleans House and the Monroe County Tourist Development Council. Performers interested in competing can email [iftheshoefitskw@gmail.com](mailto:iftheshoefitskw@gmail.com) and download the rules and application forms from bourbonstpub.com.