Lake Shore Serenade – Windy City Stop
With Dandy Wellington

September 26, 2025

IMSS is thrilled to welcome Dandy Wellington for a 3-day special event combining cocktails, conversations, concerts, and more! Centered around the history of IMSS’s storied Lakefront mansion home, the weekend will feature music and dress from the gilded age through special museum tours, panel conversations about the vintage lifestyle, and performances blending the unique sounds of 1920’s Chicago and Harlem Jazz.

On Friday at 6:00pm, we’re kicking off the weekend with an exclusive VIP tour – only 50 spots available – with drinks and a tour of our historic 1917 building followed by an evening of cocktails and intimate arrangements of Chicago & Harlem jazz performed by Dandy Wellington and his Red Hot Boys at 7:00pm. Your ticket includes refreshments and 4 drink tickets.

Friday Tickets

6:00pm-7:00pm
-Friday VIP Tour & Pour at 1524 – $45 add-on
Limited spots available!

7:00pm-11:00pm
-Friday Lakeshore Serenade Early Bird – $50 (Until July 1st)

-Friday Lakeshore Serenade Presale – $65

About Dandy – Presenter, Moderator, Panelist:

For over 15 years, Dandy Wellington has captivated audiences and facilitated meaningful conversations from behind the microphone. Whether hosting corporate events for AirBnB and Connecticut Children’s Medical Center, moderating panel discussions on the RMs Queen Mary II, or conducting one-on-one interviews with Dita Von Teese and Paula Sutton at Goodwood Revival, Dandy brings an authentic and seasoned approach that fosters deep connections with guests and enhances the integrity of events.

As an emcee, Dandy Wellington has, since 2009, been the voice of corporate gatherings, weddings, vintage and variety events at breathtaking venues such as The Beaker Palm Beach, The Rainbow Room, The Beverly Hills Hotel, Grand Hotel Tremezzo in Lake Como, Italy and more. His clients include but are not limited to Elan Artists, The Plaza Hotel, The Great Gatsby Party, Scarlet Entertainment, The Galveston Historic Foundation, Prohibition Productions, Dances of Vice, The Champagne Riot, The 1940s Ball, and The Soapbox Presents.

As a panelist and interviewer, Dandy has engaged in discussions with academics, historians, stylists and influencers – including Shantrelle P. Lewis, Monica L. Miller, Ph.D., Douglas Jones, Ph.D., Justin J, Natty Adams, Jessica Kellgren-Fozard, Raissa Bretana, Quentin Thrash and Alphonso McClendon – at venues such as the National Museum of African Art, Smithsonian Institution; and the Fashion Institute of Technology