#20: Will Smith & Jada Pinkett Smith
Estimated Cost: $1.5 million
Will Smith and Jada Pinkett married on New Year’s Eve in 1997 at The Cloisters near Baltimore, Maryland. The ceremony was private and intimate, but no less luxurious. The couple reportedly booked the entire venue, filled it with white roses and orchids, and treated guests to a candlelit dinner and live music.

Jada wore a champagne-colored, velvet Badgley Mischka gown, while Will arrived in a white tuxedo. The couple’s attention to detail and love for ambiance turned the evening into a soulful celebration — classy, personal, and effortlessly elegant, perfectly reflecting their enduring Hollywood partnership.
