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Janet Jackson beamed in bright orange for her performance after the Kentucky Derby last night.


The 55-year-old was serious as she took to the stage in a sleek suit with a performance-ready athletic twist, complete with sneakers. The star slipped into a jumpsuit with a fitted v-neck top that tucked into loose wide-leg pants and was polished with a silver buckle belt. The look was given a high fashion twist with a cropped blazer jacket that had dramatic gathered sleeves and long structured cuffs.

Jackson accessorized with a matching orange choker necklace. The “That’s the Way Love Goes” singer prioritized comfort for her performance and donned a pair of white lace-up sneakers. Jackson performed with the R&B group, New Edition.

It wasn’t the only fashion statement that caught the eye this weekend. Danneilynn Birkhead, daughter of Larry Birkhead and the late Anna Nicole Smith, paid tribute to the singer’s style on the eve of the derby. The 15-year-old attended the 33rd annual Barnstable Brown Kentucky Derby Eve Gala on Friday in almost the exact same outfit Jackson wore to the party in 2003.

Birkhead wore a black suit and tie with a brown flower brooch, a white collared shirt, and a flat cap. She also wore the hallmark of Jackson’s 19-year-old look, a large corset-style leather belt with cutouts in various shapes.

Larry posted a photo with his daughter at the event with the caption: “On our way to the Barnstable-Brown gala with Dannielynn. Dannielynn is wearing Janet Jackson’s personal outfit that Janet wore to the 2003 Barnstable-Brown gala. It was purchased as part of Janet’s @juliens_auctions to benefit charity.


Check out the gallery for Jackson’s style evolution.

Slip into a pair of white trainers this spring.

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Sam Edelman Ethyl lace-up sneaker

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