Sharp Dressed Man Casino Night

Saturday, November 21, 2026 | 7:00–11:00 PM
Baltimore Streetcar Museum

Get ready for an unforgettable evening of style, celebration, and community at the Annual Sharp Dressed Man Holiday Gala! Step into a night filled with excitement as you enjoy casino games, delicious food, an open bar, historic streetcar rides, raffles, dancing, and plenty of surprises throughout the evening.

Try your luck at the tables for a chance to win our grand prize—a custom-designed Christopher Schafer Clothier sport coat—along with other incredible raffle prizes.

Dress Code: Formal Attire

Every ticket purchased and every dollar raised helps Sharp Dressed Man continue providing professional clothing, grooming services, and renewed confidence to men preparing for employment, recovery, and a fresh start.

Join us for a night of fun, generosity, and impact—because a great suit can change a life.

Your Ticket Includes:

Casino game buy-in
Open bar
Delicious food
Unlimited historic streetcar rides
Entertainment and dancing
Access to raffles and prizes

Tickets: https://givebutter.com/SDMCASINONIGHT

Sponsorship opportunities are also available. Partner with us to make an even greater impact while gaining valuable recognition for your business or organization.

Sharp Dressed Man Casino Night

November 21, 2026 | Get ready for a night of fun, community, and impact at our annual holiday gala!

Team Members