RihannaRihanna's Diamond Ball, Los Angeles, America - 10 Dec 2015WEARING DIOR

Autumn in New York brings crisp weather, Central Park foliage and — perhaps most importantly — gala season. Hot off the heels of New York Fashion Week, the fund-raising circuit unofficially kicks off mid-September with Rihanna’s third annual Diamond Ball on Sept. 14. Donning tuxes and gowns, the city’s philanthropic set will drift between Cipriani uptown and downtown and all glittering venues in-between to see and be seen while raising money for worthy causes. Here’s our list of some of the most anticipated (mostly) black-tie affairs this season.

The Clara Lionel Foundation’s Diamond Ball

Hosted by Rihanna, the third annual fund-raiser dinner coincides with the end of New York Fashion week and will be hosted at Cipriani Wall Street by Dave Chappelle with performances by Kendrick Lamar and Calvin Harris. The star-studded evening will benefit the “Work” singer’s initiative to support health-care and education programs around the world.

Keep A Child Alive Black Ball

Touted as an “evening of music and philanthropy,” singer Alicia Keys will be joined by fellow musical luminaries and passionate activists this October in helping to realize the end of AIDS and HIV for children and families. While this year’s performances have yet to be announced, it’s safe to say Keys will once again tickle the ivories. Last year’s acts included Chance the Rapper and Salt-N-Pepa.

Gabrielle’s Angel Ball

One of the most anticipated events of New York’s social season, the annual Gabrielle’s Angel Foundation gala attracts nearly 1,000 supporters raising money for cancer research. Held at Cipriani’s Wall Street location, tickets to this year’s dinner on Oct. 23 start at $1,750, which includes the opportunity to potentially rub elbows with the likes of past guests including Hugh Jackman, Tommy Hilfiger, Donna Karan and Sarah Ferguson, Duchess of York.

Naked Heart Foundation x amfAR Gala

Hosted by Natalia Vodianova, the Naked Heart Foundation will partner with amfAR for a Halloween-themed party being held in New York for the first time on Oct. 28. Earlier this year the model teamed with pal Karlie Kloss for London’s Fabulous Fund Fair — complete with a dazzling indoor carousel. This All Hallow’s Eve event will certainly be an over-the-top celebration raising money for families in Vodianova’s native Russia as well as the AIDS Research nonprofit.

Whitney Art Party

Typically attracting a younger set of art supporters, the annual event skips dinner and goes straight to cocktails and dancing alongside the Meatpacking District gallery’s collection with proceeds benefiting the museum’s Independent Study Program and other education initiatives. While this year’s hosts have yet to be announced, last year saw Karlie Kloss and Brandon Maxwell cochairing the soiree.

Guggenheim International Gala

Raising money to continue the Upper East Side museum’s exhibition program, this annual black-tie dinner held on Nov. 16 within the soaring Frank Lloyd Wright modernist space is again sponsored by Dior, which means the party pictures will not disappoint. Past guests have included a mixture of creative types including Jeff Koons, Cindy Sherman, Raf Simons and Natalie Portman.