Janet Jackson Flashes Her Signature Smile As She Rocks Sweats After Kentucky Derby: Photos

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Janet Jackson proved that she can pull any outfit off! On May 8, the legendary singer and dancer was seen outside the JFK Airport in New York City after a performance in Louisville, Kentucky after the Kentucky Derby.

In the candid photos, Miss Jackson looked laid back as she rocked a matching gray hoodie and sweatpants combo with chunky white sneakers, a large scarf, and some seriously cool shades. She also appeared to be in good spirits, with a cheeky smile on her face.

Her upbeat mood came with a good reason, as her post Kentucky Derby show with New Edition was a massive hit, according to WLKY in Louisville, Kentucky. “She’s a boss, the standard, the blueprint, a legend, I mean she’s the icon,” one excited fan at the concert raved. Surprisingly, the show was Janet’s first live performance in three years.

However, the successful concert wasn’t Janet’s only fun endeavor that week. She attended the Barnstable Brown Gala on May 7, an event celebrating the Kentucky Derby. At the ceremony, she looked sleek and sharp in an edgy black trench coat.

Better yet, the “Feedback” singer took some adorable photos with Anna Nicole Smith‘s 15-year-old daughter, Dannielynn Birkhead, and her father, Larry Birkhead. That night, Dannielynn was coincidentally wearing the exact outfit Janet wore at the same event in 2003! It was purchased at a charity auction, according to Larry. The 49-year-old photographer also had nothing but positive things to say about Janet in a post on his official Instagram account.

“What a night! Dannielynn got to meet @janetjackson at the Barnstable-Brown Gala, while wearing Janet’s outfit that she wore to the same party in 2003. Janet was so gracious and complimentary of Dannielynn in her outfit. She made Dannielynn so happy and even graciously posed for a photo with us,” the caption read.

In first snapshot, the three stood amongst a busy crowd under blue lighting, directly facing the camera. Along with her award winning smile, Dannielynn sported Janet’s elegant suit and her cute black cap, giving off some serious “Rhythm Nation” vibes. In the second photo, the three are looking away from the camera, appearing to be engaged in conversation, with Janet demonstrating her typically shy but friendly demeanor.