'Uncomfortable Shoes' & 'Pajama Skirt': Taylor Swift's Date Night Outfit with Boyfriend Travis Kelce in NYC Ignites Buzz

The couple may have stepped out of a Michelin-starred restaurant, but it was the pop icon's uneasy steps and unexpected outfit that stole the show, triggering a digital firestorm across social media.

Taylor Swift's latest date night look with Travis Kelce over the weekend had fans and critics buzzing online, mostly about her outfit, which some described as "model off duty," while others wondered if she "dressed in the dark."

The pop star and the NFL player tight end were photographed leaving a New York City restaurant after having a Michelin-starred meal at Torrisi over the weekend, holding hands as they stepped into the night.

Swift wore a scoop-neck corset in sweet cornflower blue and a pale pink poplin mini-skirt. She styled her look with a cream mini cloud cross-body bag and heels in a similar creamy tone.

The pop icon added a diamond watch, finishing her outfit with an opal necklace and gold chains, with a bow and arrow pendant. Swift kept her signature red lip and wore her hair long and loose with a thick set of bangs.

Kelce also stepped out in summer clothes. The Kansas City Chiefs player wore a pale blue and navy collared U.S. soccer polo shirt, with cream linen bermuda shorts, white sneakers, and white socks.

The outfit quickly set social media ablaze, leaving their fan base with mixed reactions. An Instagram user echoed the discomfort theme, writing, "She dresses like a tween. And no matter what always looks like she was dressed in the dark [sic]"

Another added, "She looks really uncomfortable in those shoes. I’ve seen videos and she can barely walk in them.[sic]"

Another Instagram user on DeuxMoi's post commented, "So weird with a 35 year old woman dressed like a 9 year old ballet dancer. But I am guessing that’s her fanbase. [sic]"

Another chimed in with praise, saying, "I love her outfit, very model off duty ... also her legs are crazy 😮❤️" But the reactions were far from one-sided. One skeptical user asked bluntly, "Is that a pajama skirt?!"

Over on Reddit, fans and users continued dissecting the look and Swift's apparent struggle with the shoes. One noted, "Right! All that dancing on stage and touring. Nice runner looking legs, healthy."

But another observed, "I think she was wearing horribly uncomfortable shoes and had trouble walking in them [sic]"

One detailed comment read, "Yes, in the photos of them leaving you can see how red her feet are lol. The shoes definitely didn’t fit her properly. She probably had a drink or two at dinner because why not but her feet look painful too. [sic]"

A final user concludes, "Both their legs look amazing but this is also giving 'learning how to walk [sic]'"

Still, the online buzz didn't stop at her shoes or skirt, as Swift's recent looks have also ignited another wave of speculation entirely. Just a few months ago, in May 2025, the couple was spotted on a date night in West Palm Beach, Florida. Many fans couldn't help but speculate about what Swift's outfit meant.

The singer wore a delicate white off-the-shoulder dress adorned with a soft floral pattern, paired with a black handbag. Kelce kept it casual in a black-and-white patterned short-sleeve shirt, white pants, and a black cap.

The couple's stylish appearance quickly caught attention, not just for fashion, but for what many believed it hinted at. Online, fans shared their thoughts, with several suggesting the singer might be expecting.

"That is a pregnancy belly," one comment read, while another simply said, "I think she is pregnant, wow." A third person added, "She's giving pregnant vibes…"

Amid the speculation, others praised her look. "She looks so good omg," one admirer wrote. Some stayed focused on the possible news, calling it "pregnant vibes," while another viewer remarked, "They are giving husband wife/ spouses."

Likewise, the couple also turned heads in March 2025, when they had a quiet dinner at Del Frisco's Grille in New York City, adding to the pregnancy speculations.

That evening, the songwriter wore an oversized gray blazer-style jacket, paired with sky-high maroon heels and a black handbag. The NFL star, seen beside her, sported a laid-back look with light blue jeans and a loose button-up shirt.

Online reactions followed quickly. "Baby bump," one person noted, while another wrote, "She's preggers y'all 😍." A third pointed out, "Maybe she's pregnant… being that sneaky and wearing a big jacket." Someone else joined in with, "I think she is pregnant."

Others had different takes. "Maybe they were on their honeymoon," a comment read, while another added, "I think they're planning the secret wedding." One fan focused on their style instead, sharing, "The matching outfits❤️❤️❤️❤️❤️❤️❤️❤️❤️."

Whether it's a daring skirt, a bold heel, or a softly draped floral dress, every step Taylor Swift takes with Travis Kelce seems to spark more than just flashbulbs. It ignites fresh speculation, unending fan theories, and a cultural obsession that shows no signs of slowing down.