A Miami Boutique Built for Second Chances takes Center State at LEAP's Celestial Masquerade
At Dragonfly Boutique in South Miami, the racks hold carefully selected fashion, accessories, home goods, and occasional designer discoveries. Behind the boutique is another kind of curation: a Miami nonprofit model designed to ensure that women returning from incarceration have more than preparation for employment. They have a place to begin.
On Friday, October 30, 2026, the Ladies Empowerment and Action Program will bring the community behind that model together for the LEAP Second Chance Gala: Celestial Masquerade, an immersive evening at the Rubell Museum celebrating 17 years of impact.
The gala aims to raise $250,000 to support LEAP's incarceration-to-community programming, which begins through trauma-informed education inside prisons and Miami-Dade County jails and continues after release through housing, reentry support, workforce development, and paid employment.
LEAP Built the Employer Women Needed
LEAP launched Dragonfly in 2018 after repeatedly encountering the same barrier: women could complete classes, counseling, and job-readiness training, yet still struggle to find an employer willing to offer an immediate opportunity.
Dragonfly became that employer.
The social enterprise offers three-month paid internships through which women gain income, workplace experience, retail and technology skills, and professional references. Some interns earn permanent roles within the boutique.
For many participants, that first paycheck supports the practical beginning of reentry like groceries, transportation, rent, and the ability to make decisions with greater independence.
“Even more incredible, I had a job waiting for me at Dragonfly. That opportunity gave me stability, purpose, and dignity,” said Stephanie R. (LEAP Graduate, Class 25).
In October 2025, Dragonfly relocated to South Miami, bringing the boutique and LEAP's program operations under one roof. Its donated inventory is carefully organized and priced accessibly, with clothing, accessories, home goods, and a dedicated designer section creating a shopping experience that is warm, personal, and distinctly local.
“We realized that support could not end with preparing someone to work,” said Mahlia Lindquist, Executive Director of LEAP. “Women needed an actual employer, somewhere they could earn income immediately, build a work history, and be seen for their abilities. Dragonfly gave us a way to create that opportunity while inviting the wider Miami community to participate.”
A Local Perspective on Fashion and Value
As fashion increasingly embraces resale, longevity, authenticity, and intentional consumption, Dragonfly offers a Miami perspective on what those values can make possible.
The boutique sits within a larger cultural conversation about how value is defined: by quality, history, individuality, local connection, and the impact created by a purchase or donation.
A designer piece from a previous season can become inventory. That inventory can help fund a paycheck. The paycheck can help a woman begin building stability after incarceration.
Fashion is the entry point. The opportunity it creates is the larger story.
Since 2009, LEAP has served more than 2,000 justice-impacted women and delivered more than 60,000 hours of retail and technology job training. More than 450 women have graduated from its in-prison program, and the organization reports recidivism below 7 percent among prison-program alumnae, compared with an approximate U.S. average of 58 percent.
Celestial Masquerade at the Rubell Museum
The October gala will translate LEAP's themes of visibility, possibility, and transformation into an experience unfolding at the Rubell Museum.
The evening will include performances by LEAP graduates, a special selection of songs from Phantom of the Opera arranged by Radmila Lolly, tarot readings, food stations, live and silent auctions, and a 360-degree photo experience.
Guests will be invited to write wishes on dragonflies and add them to a constellation wall that develops throughout the evening. Custom luxury keychains by Piper & Skye, crafted from invasive lionfish skin, will introduce additional elements of design, reinvention, and second chances.
Celestial cocktail or evening attire is encouraged. Masks, metallics, sparkle, and night-sky-inspired details are welcome, with masks optional.
Honoring the People Behind the Work
The 2026 gala will recognize individuals and organizations whose work has helped create pathways forward for women impacted by incarceration:
Program Stars: Corinne Webb and Shed Boren, former LEAP instructors
Corporate Star: Lennar Foundation
Community Star: Ivon Mesa of the Miami-Dade County Department of Corrections and Rehabilitation
“LEAP has been a trusted partner to the Miami-Dade Department of Corrections for over 15 years, providing life-changing programs that truly prepare women for success after incarceration,” said Mesa.
Event Details
LEAP Second Chance Gala: Celestial Masquerade
Friday, October 30, 2026
6:00 p.m.–11:00 p.m.
Rubell Museum
1100 NW 23rd Street
Miami, Florida 33127
Tickets, tables, and sponsorship information:
About LEAP
The Ladies Empowerment and Action Program supports women impacted by incarceration through an incarceration-to-community model encompassing trauma-informed education, workforce preparation, housing, reentry services, employment, job training, and long-term community support.
Dragonfly Thrift Boutique is LEAP's social enterprise, providing paid internships and workforce experience while generating revenue to help sustain the organization's broader mission.
For more information, visit LEAPforLadies.org.