Denim & Diamonds: A Sparkling Night of Community

From left: Chrissy Wittmann of The Prisoner Wine Company, Melissa Schwartz, and Lisa Howard of Tolenas Winery on stage at Denim & Diamonds.

We’re deeply grateful for your incredible support at our 2025 Denim & Diamonds: A Toast to Women’s Winemakers. You were the most generous group at this event yet, increasing night of donations by 62% year over year. Thank you! Your generosity made the night a true success—full of laughter, celebration, and moments that will ripple through our Dress for Success community and beyond.

A special thank you to Lisa Howard of Tolenas Winery and Chrissy Wittmann of The Prisoner Wine Company for sharing their craft and spirit with us. While both winemakers shared differences - Tolenas is a small family-owned winery (approximately 2,000 cases of wine a year) and The Prisoner Wine Company is a larger brand (approximately 170,000 cases of wine per year) - we learned there are also similarities. Both winemakers never anticipated getting into the wine industry and shared that while drinking wine may be glamourous, making it is incredibly hard - and rewarding. It was endearing to see their relationship blossom on stage with some good-natured ribbing between the two.

Special thanks to the fabulous Melissa Schwartz for moderating our winemaker discussion.

We’d also like to thank all of our sponsors of the event, and the generous donations for our live auction! Our first-ever Pop-Up Shop Accessories Table was a hit with over 40% of attendees bringing something home.

And heartfelt thanks to Auburn, our Client Ambassador, for courageously sharing her story and inspiring the room. Beyond the sparkle, the real win is the impact your support will have on Auburn and the many women we serve.

In 2022, Auburn came to Dress for Success through the Career Wardrobe program while studying at Mission College and living in shelters. After her appointment she felt incredibly confident and was excited to secure her first apartment. Unfortunately, her relationship turned into 14 months of domestic abuse. Two years later she returned to Dress for Success without any confidence seeking a safe place to rebuild—leaning into Career Coaching, Job Search Prep, and Google Career Certificates.

Since graduating from our Virtual Job Search Training, she’s earned her liberal arts degree, is finishing a social justice degree this fall, and just began a Peer Support Internship at Momentum for Health to uplift others on their recovery journey. Dress for Success helped Auburn reclaim her voice and her confidence. Both were on display at Denim & Diamonds where Auburn truly wowed the crowd with her honesty and gratitude for Dress for Success.

Because of you, more Bay Area women will have the clothing, coaching, core skills, and community they need to move from interviews to meaningful work.

Big thanks to our photographer, Tony Chew, for capturing the spirit of the evening. Photos of the event coming soon! And who could forget our epic photobooth from Creative Lei. Check out all the fun moments in this gallery.

We also want to extend our appreciation and a big hearty thank you to our incredible volunteers. Without you, this event would not be possible.

With deep gratitude to every supporter—your gifts made the night a success and the future brighter.