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Markle, the Duchess of Sussex, stepped out Wednesday night in a sparkling evening gown by Roland Mouret that she paired with a Givenchy clutch.
The stunning dress immediately drew comparisons to a sequin gown by Catherine Walker that Princess Diana wore on at least three occasions in the 1980s and '90s.
Markle, who is expecting her first child with Diana’s son, Prince Harry, also accessorized her dress with a bracelet that once belonged to Diana, who died in 1997.
Markle, 37, previously wore the bracelet last year when she and Harry visited Sydney.
The Duchess of Sussex also drew comparisons to her late mother-in-law on Monday when she stepped out alongside Prince Harry in bold color choices of purple and red.
She paired a purple Babaton by Aritzia dress under a red winter coat by Sentaler, a Canadian brand, and completed the look with red heels.
Princess Diana wore the same purple and red color scheme on several occasions in the late 1980s. Diana's look consisted of a purple skirt and red blazer by Catherine Walker paired with a matching hat by Philip Somerville.
She also wore a red and purple gown, also by Catherine Walker, during a visit to Bangkok, Thailand in 1988.
Markle carries a piece of Princess Diana with her at all times, through her engagement ring.
The ring's center stone is flanked by two diamonds from Diana's personal jewelry collection.
"The little diamonds on either side are from my mother's jewelry collection to make sure that she's with us on this crazy journey together," Harry told the BBC's Mishal Husain last November in the couple's first interview after announcing their engagement.
Markle described how touched she was by Harry's design choices -- especially the ring's link to his mother.
"I think everything about Harry's thoughtfulness and the inclusion of [Diana's stones] and, obviously, not being able to meet his mom -- it's so important to me to know that she's a part of this with us," she said. "It's incredibly special to be able to have this, which sort of links where [Harry comes] from and Botswana, which is important to us. It's perfect."