Taylor Swift's Best And Worst Date-Night Outfits With Travis Kelce

We've seen plenty of Taylor Swift's best and worst game-day looks, but she's also stepped out in some hit-or-miss outfits on date nights with her husband Travis Kelce. For the most part, the "Red" singer really nails it, wearing everything from classy black dresses to fun floral prints. On the other hand, a few of her outfits have left us questioning her choices. It doesn't come as much of a surprise that she isn't always consistent in the fashion department. Fans have taken to social media at times this year to critique some of her outfit choices.

While no one is doubting that Swift is capable of serving looks or that she and Kelce are super cute together, we do collectively sigh whenever we see something that doesn't quite work for her. She's been caught in things like a printed peacoat and checkered corset top. Not Swift's best, but we're here for it all — the highs and the lows. We've taken the liberty of rounding up her best past date-night looks while out with Kelce and a few that were flops. Taylor Swift redeemed her style reputation with a sleek 2026 VMAs look, and we hope she continues on this upward spiral.

Taylor Swift was spotted earlier this month wearing this date-night number while out with Travis Kelce in New York in October 2026, and it's quickly become a favorite look of ours. We love that it really nails the casual-cool date-night aesthetic. The oversized leather jacket adds an edgy element to an otherwise simple little black dress, giving huge "Reputation" vibes. Paired with the strappy heels and small leather bucket bag, the whole outfit feels put together but not overly formal.

In May 2026, Taylor Swift stepped out with Travis Kelce in an olive green formal maxi dress. While there's nothing wrong with this look in any way, we've just seen better outfits from Swift, so it's a flop in comparison. This dress isn't quite as flattering as her all-black date-night outfit. Besides, we've also seen Swift do better in the formal department. While the neckline is really gorgeous, the waist area looks a little wrinkled, and the color is too dull to actually make her shine.

Taylor Swift proved that it doesn't have to be daytime to rock a garden party-chic look. This floral maxi dress is something a little different for the "Patient Zero" singer, and we love it. The off-the-shoulder cut is elegant and feminine — perfect for date night. She paired the dress with simple jewelry, a soft pastel yellow bag, and knotted strappy heels, which further added to the spring aesthetic. 

It's been lovely to see the stunning style transformation of Taylor Swift over the years. She's more than proven that she can pull off a successful leather outfit, but this one was a miss for us. Swift paired a camel-colored coat with a beige and black corset top, leather skirt, and boots. The whole ensemble might have been more successful with a black coat. However, the print of the corset top just doesn't scream "date night," so there's not much to do to save this look. 

As we said, some of Taylor Swift's best date-night outfits are all black, and this one can easily be added to that list. The black three-quarter-length sweater and skirt are simple, but Swift decided to add a pair of floral mesh tights underneath, adding a unique touch to the look. She topped it all off with a pair of knee-high black leather boots, a vintage-looking purse, and a classic red lip. This look is peak Taylor Swift — classic with a little added flair.

While this all-black outfit would have been really cute otherwise, Taylor Swift's coat choice here was what didn't quite work. The print is a little odd and throws off the whole outfit. We see what Swift was trying to go for. This shot of her and Travis Kelce was taken on December 28, so she may have been going for a Holiday vibe, but it didn't work. Love the idea, but the execution needed some work here.