The jet, which departed from New York’s Teterboro Airport at 6:15 a.m. under clear skies, carried the couple on a stylish and stealthy flight. According to eyewitnesses, Swift and Kelce traveled incognito, both sporting oversized sunglasses. They spent the two-hour journey reviewing their event schedule and sipping mint julep-inspired mocktails crafted by their personal flight attendant.
Swift, dressed in a breezy white linen blouse and wide-leg trousers, was seen sketching hat designs in a leather notebook—perhaps hinting at another iconic Derby headpiece. Kelce, ever the meticulous athlete, reviewed the day’s track conditions on his tablet with the same focus he brings to NFL Sundays.
Upon landing, the couple made a brief but dazzling appearance in the airport’s VIP lounge. Swift’s stylist quickly secured a peach-colored fascinator atop her golden curls, while Kelce, in a navy blazer and crisp white shirt, added a silk pocket square in signature “Derby pink” to complete the look. Local photographers snapped shots of the duo exchanging warm smiles before they were whisked away in a black SUV adorned with Derby insignia.
Their first stop? The historic Brown Hotel, a Louisville landmark synonymous with Southern charm. Sources confirm the couple checked into adjoining suites with sweeping views of downtown. Plans for the evening reportedly included a romantic dinner at the hotel’s famed English Grill, where the two were expected to enjoy the legendary “Hot Brown,” an open-faced sandwich that has become a Derby Eve tradition.
Insiders say the itinerary doesn’t stop there. Swift and Kelce are set to attend Friday’s exclusive Oaks Day charity luncheon before making their highly anticipated appearance in the Turf Club on Saturday for the main event. Fans are eagerly awaiting the reveal of Swift’s custom-designed hat, rumored to be one of her most daring yet, and Kelce’s tailored seersucker suit — a sartorial pairing that’s sure to make headlines in Derby fashion history.
With their arrival, the energy in Louisville has skyrocketed. Social media is already flooded with fan sightings, style predictions, and endless speculation about what the couple will wear — and whether they’ll walk the red carpet at Churchill Downs hand-in-hand.
One fan posted, “This is NOT a drill. Taylor and Travis have landed. Derby weekend just became legendary!”
And if this dazzling entrance is any indication, the Kentucky Derby 2025 is shaping up to be a show for the ages — both on and off the track.
