It’s been a minute since Taylor Swift stepped out in New York and didn’t care about being pap’d. That’s what happened yesterday – Taylor was out and about in New York with her dad and then, later in the day on Monday, she was out with friends too. There have been so many conspiracies about Taylor’s recent undercover era too, with many fans suggesting that Taylor is deep into wedding planning and she’s trying to keep her movements quiet so her wedding doesn’t turn into a circus. I sort of believe that too, and I believe that Taylor and Travis Kelce will have their wedding before his football preseason starts in August. Your guess is as good as mine when it comes to the where and when of it all, but I suspect “Rhode Island in June or July.”
As for these photos, Taylor spent the afternoon and evening at The Jane Hotel (for dinner) and then San Vicente West Village with Jerrod Carmichael, Jack Antonoff and Ashley Avignone. Her outfit is… fine. I actually like her sundress and the Dior purse, but I’m not sold on the shoes. I have a theory about this too – I think Taylor is still sort of stuck in her Sex and the City fantasy and she thinks she can just throw together slightly random-yet-high-end looks and that makes her the New Carrie Bradshaw. Is she right?? The bag is the mini Lady Dior, which retails for $9,750 (insane). Her dress is from Staud, and it retails for $325. Her shoes are $1,195 Christian Louboutin. (Note by CB: Shutz’s Olga leather sandals are a more affordable alternative at $198 and Old Navy has a Fit and Flare sleeveless midi dress that’s similar to Taylor’s for just $25!)
The other Taylor news this week is that she’s filed trademarks on her voice and likeness, likely to protect herself and her music from all of this AI bullsh-t. Considering that Donald Trump has literally posted and amplified AI-generated images of Taylor Swift, I don’t blame her.
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- New York, NY Taylor Swift, Ashley Avignone, Jack Antonoff, and Jerrod Carmichael step out together at San Vicente West Village in New York Pictured: Taylor Swift BACKGRID USA 27 APRIL 2026 BYLINE MUST READ: JosiahW / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
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- New York City, NY Taylor Swift is spotted leaving the Jane Hotel restaurant after enjoying dinner with her father and her friend Ashley Avignone. Pictured: Taylor Swift BACKGRID USA 27 APRIL 2026 BYLINE MUST READ: Jairo / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
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- New York City, NY Taylor Swift is spotted leaving the Jane Hotel restaurant after enjoying dinner with her father and her friend Ashley Avignone. Pictured: Taylor Swift BACKGRID USA 27 APRIL 2026 BYLINE MUST READ: Jairo / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
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- New York, NY Taylor Swift is spotted stepping out of The Jane Hotel restaurant after having dinner with her parents in New York. Pictured: Taylor Swift BACKGRID USA 27 APRIL 2026 USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
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- New York, NY Taylor Swift is spotted stepping out of The Jane Hotel restaurant after having dinner with her parents in New York. Pictured: Taylor Swift BACKGRID USA 27 APRIL 2026 USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
It’s a cute dress and the purse is fine but the shoes are a misstep. Too dark and klunky. Tan espadrille wedges would be good and more summery. Or lean into the yellow colorpop and go for yellow shoes. Kitten heels or flats could work.
There’s a level up to a luxury life YouTuber I’ll watch occasionally. She had a “fashion lessons from Taylor Swift” video. Best thing about it was when she had to pause the gushing, look to the camera and tell her viewers that Taylor Swift wears terrible shoes and if they want to be elegant ladies in high society, they should not wear shoes like Taylor Swift’s. Cracked me up.
That’s what I was just thinking! The blue dress and the pop of yellow are great, but the shoes bring the outfit down. Nude, tan, or yellow (or hell, even a deep blue!) would all look better.
The light blue dress and red shoes are very “Dorothy Gale.” Is it that warm in NYC already?
Agreed on the Dorothy aesthetic. And the purse is very yellow brick road.
Ohh, it is very Dorothy coded! Great catch. At least she didn’t add a (toy) dog.
Nope, not sundress season.
I don’t hate any of these items, they just don’t go together. I don’t begrudge her the joy of putting outfits together with her hard-earned money. Must be fun. I’d enjoy having a stylist help me more, though. She reminds me of her ex-bff Blake Lively. I think Blake loved how well she wore the outfits the Gossip Girl stylists put together for her and she thinks she can do it too. She can’t. They both give “having fun in the mall with my first intern salary”.
Bingo!!!
Yes, I love the pieces individually. I look for Staud dresses (on sale/aspirationally) and I think the Lady Dior bags are stunning. I’m impressed she can walk in Louboutins in general, and especially with the cameras in her face.
But you’re right; together something’s just off. I know I enjoy clothes, accessories, etc. but I know I can’t visualize to that level and would absolutely want a stylist at that level to push me and optimize everything. Oh, to have that money and easy figure to dress.
I like the clothes but the makeup, especially the eyeliner, is too much and has a way different vibe than the outfit.
The Dior bag is gorgeous but over $9,000? Taylor’s fanbase is struggling with the ever-rising costs of food and fuel. I’m disappointed she’s so tone deaf in this moment.
As someone said on social media the other day, “Peanut butter AND jelly? In this economy?”
Also now reviewing her outfit, I find it confusing. The purse and dress are fine, but the brown sandal really doesn’t work. Maybe white or beige. Something more delicate? Those sandals look best for jeans or pants. But what do I know? I wear tennis shoes or Birkenstocks everwhere.
Swiftie here, I love watching her dress up in all the bling she’s earned. We don’t say that of other celebrities wearing ultra exy outfits, yet they’re on sm and written about every day.
I’m sorry but Taylor is worth 1.6 billion, that bag isn’t more than a candy bar to most people. I would be more offended if she wasn’t spending her money and helping all the people that bag employs.
Taylor does a lot of charity, she will go to go fund me and pay it off, etc. she can and should buy what she likes even if some are struggling it’s not like she’s hoarding her money. She also tried to get people to vote for someone else.
I’m an old, so have never really paid much attention to Taylor Swift until I started reading CB a few years ago. I had no idea she was such a bad dresser. Like really bad. She always looks… just off. God bless her, but she just can’t dress herself. I love this sundress, but it’s awful with those shoes.
Go look at pics when she was a “country singer.” She’s always had really unsophisticated taste.
Huh. I usually hate her street style but I am a fan of this look. The shoes aren’t quite doing it for me but overall I think this is a win for her.
I agree, Becks. This would be a perfect summer look.
I get too chilly to wear sundresses in April, but Taylor gets ferried everywhere — and she’s probably had to get used to chillier temps because Travis is a large and hairy man who likely keeps the thermostat low LOL.
I like everything she’s wearing but agree that the shoes are a little off with the dress. If you have limited space and money, it makes sense to wear to your really nice medium brown heeled sandals with a blue and white dress. And those actually look like you could walk in them on NYC streets and be somewhat comfortable. But she can more than afford to switch it up (and take a private car), so she should have gone with a lighter shoe.
I think the shoes and dress are totally fine together. I like it a lot! The 10 000$ hand bag is absolutely bunkers though. Just nuts.
I will actually be attending a wedding in Providence Rhode Island on June 13th, I’ll let you know if I see any suspicious activity around town before then!
Travis and Jason have a New Heights live appearance lined up in LA on June 15th, you can buy tickets.
It’s looking like July 3rd in NYC so they can invite all the people they want, no shortage of hotel rooms, keep it indoors, controlled, no helicopters, and lock out the media. TMZ has been following Mama Kelce everywhere to figure out when/where the wedding is and it’s been a gross situation for the family. They even covered her installing new energy efficient windows and doors for her condo a while back. She can’t even go to the mall without being followed and questioned.
I agree it’s not going to be RI. Too easy for helicopter fly overs and not enough accommodation close and discreet to the venue. NY wouldn’t surprise me but I ‘m still putting my money on an island destination wedding.
I like her and wish her well but someone needs to tell her to fix her posture.
I came here to say the same thing about the dress. I bought Old Navy fit n flare denim dress and returned it since I thought it was very Taylor Swift (and I’m 57 lol). So I returned. It’s cute! Comes in Tall sizes too!
I always feel like she dresses as if she’s 5’ 5” but Taylor, us tall ladies will never pull off “cute” and we need to come to terms with that 😅
THE JANE! I spent the worst night of my life at the Jane Hotel. It was Dec 30, 2008. I was staying on my own for one night before meeting up with my BFF, I had heard of this new up & coming hotel, it was dirt cheap. It was just a room – it was a “former” Y – with shared bathrooms on the floor; I figured it would be fine. My first warning was when I saw that the check-in desk was literally under construction. My second warning was that when I was walking to my room, I saw that some rooms had doormats outside of them.
Long story short: the cabbie picked me up on my way to meet up with a friend and said the place had bedbugs; I went out with that friend and came back WAY too inebriated, felt sick to my stomach. The “former” Y was a current Y, and I kept going back and forth to the bathroom in the presence of random men who were hanging out in the hall. Additionally, an ex chose that night to send me an expletive-laden text, cussing me out. Now Taylor is eating there! The Jane has apparently reached soaring heights in the past 17 years (unlike myself!).
It’s funny – I don’t like the dress in that colour, I don’t like the bag, regardless of colour, but I LOVE the shoes! 😀 I used to have a black pair like that.
The fit feels way to summer-y. Like everyone in the background is still wearing coats and jackets
Agree 💯 with the fashion assessment. Money can’t buy style or class.
That said, that $10K handbag could quite literally feed families. I know she does some altruistic stuff but it’s usually performative. With the kind of money she has, start a nonprofit that could make a substantial difference in this world that sorely needs it right now. Don’t parade around with an ugly handbag that’s supposed to be aspirational but just comes off as willfully ignorant and poorly advised when so many are struggling financially.