Taylor Swift Style

Attending a wedding | Bath, England | August 15, 2026

Costarellos ‘Arcangela Appliqué Tulle Gown’ - $3,545.00 Linda Farrow ‘Cat Eye Sunglasses’ - sold outAquazzura ‘Sundance Crystal Clutch’ - $1,495.00 Kindred Lubeck engagement ring Cartier ‘Love Unlimited Bracelet’ - $9,400.00

An answer to Taylor’s presence in England! On Saturday, Taylor attended the wedding of Laura Sisk, giving us a better look at her new hair cut (which she debuted while out to dinner earlier in London) and also The Band! 💍 It appears to be a partial eternity band curved to nest against her custom Kindred Lubeck engagement ring. It makes for a complementary contrast that also picks up on the small diamonds that appear on either side of her Old Mine center stone. The hair! The new length lands just below shoulder length with a deep part + bangs styled sideswept across her forehead. Taylor has swooped her hair like this before. Often, I would guess, in between trims as well as when she first cut her hair into a bob. Given her recently freshened shorter length, I wonder if she’s slowly growing out her long-worn bangs? I’m curious to see how she continues to style and settle into this new cut.

We also got continued insight into Taylor’s wedding guest attire. A long fit + flare makes for a versatile silhouette suitable for most wedding occasions. Her navy and gold tulle Costarellos gown featured beautiful botanical appliqués, also picked up on by her gold Aquazzura clutch. The floaty fabric and embellishments suited the elevated garden party scene. I also felt her matching pearls made for an elegant styling choice. 

Sisk has contributed to a number of Taylor’s albums, beginning with 1989 (2014). This weekend, she married fellow recording engineer Oli Jacobs. Other notable attendees of the nuptials included Phoebe Bridgers, Sabrina Carpenter, and Jack Antonoff. 

Out and about | London, England | August 12, 2026

Delphine ‘Isabelle Mini Dress’ - $995.00 Christian Louboutin ‘Loubi54 Satin Crystal Clutch in Aftersun’ - $7,495.00 Aquazzura ‘Love Struck 85 Sandals in Light Bronze’ - $1,574.00

Our first peek at Taylor’s street style outing post-wedding. She was photographed leaving the members-only club Annabel's in an embellished floral mini with sparkling heels and bag to match. In addition to a new outfit we also got what appears to be a new haircut! Her fresh chop looks to land at just around shoulder-length. Getting a major cut shortly after your wedding? A classic move. It’s exciting and fun to see a new length on her after a number of years rocking it long. Here’s to seeing it styled out in the daytime for a better look!

This dress is by Delphine, the partywear sister label of Tanya Taylor - a designer known for vibrant prints and patterns that Taylor has worn in the past. A floral mini dress is a sweet and feminine staple in Taylor’s wardrobe. She’s worn plenty through springs and summers over the years, most often with heeled oxfords or sandals and a cognac leather bag. For this moment, it’s the embellishments that give that “night out” tilt. As does the coordinating sunset ombré on her Louboutin bag which hails from the brand’s Studio 54-inspired eveningwear collection plus the crystals on her strappy Aquazzura heels - a shoe designer she’s also been turning to for events and moments out. A choice I, a long-time lover of the minimalist strappy sandal, can’t help but approve. Thanks to the Aquazzura team for confirming to TSS the exact style and color. All together, the look feels like a sparkly nighttime version of something we’ve seen Taylor wear in the past. Familiar, but fun. And particularly fresh when styled with that new ‘do! 

The location may also strike a familiar note as Taylor has been photographed here before. Most notably in August 2024 to host a wrap party to celebrate the completion of the European leg of the Eras Tour. 

Attending the wedding of JuJu Smith-Schuster | Laguna Niguel, CA | July 10, 2026

Markarian 'Laila Floral Brocade Gown' - $4,115.00 Larkspur & Hawk 'Posy Earrings' - $5,200.00 100 Ways 'Vintage Diamond Bracelet' - $2,141.00

As fresh newlyweds, Taylor and Travis dove right back into the wedding scene. Together, they attended the nuptials of former Kansas City Chiefs teammate Juju Smith-Schuster’s in California. Proving that she’s developed a reliable (and consistent) wedding guest formula, my first thought was that Taylor’s floral brocade gown by Markarian carried a similar strapless silhouette to a different gown, also by Markarian, she wore to a different wedding last summer in Tennessee. Proof that fabrication and styling can completely change a look!

While likely a happy coincidence, I also thought that Taylor’s dress somehow complemented the wedding couple’s colour palette which, per Vogue, carried a “Hawaiian theme” as “a perfect nod to the groom’s Samoan roots.” She blended in with their florals perfectly!

To round out her styling, a familiar glimpse into her jewelry box with mainstay vintage pieces she's repeated over the years.

Attending Tight Ends & Friends Concert | Nashville, TN | June 23, 2026 

Monse custom dress  DLNLX Crystal Choker by Dylanlex - no longer available Aquazzura ‘You and I Metallic Leather Sandals’ - $1,025.00 

For a second year in a row, Taylor both attended and performed at Tight End University. The annual event, shortened to TEU, gathers tight ends from across the league for a week of events ranging from training, to mentorships, and yes - to a musical event! 

Last year, Taylor delivered an impromptu performance of “Shake It Off” in a short denim dress styled with a waist-cinching belt and boots. This year, a dressier approach! Given last year’s occasion was spontaneous, perhaps this is the result of pre-planning? To that, I absolutely loved the black strapless asymmetric dress. The level of detail in the hemline! My first impression was how it seemed quite fanciful for the occasion. Upon learning it was a custom piece I was intrigued! TEU is not a glamorous or high-profile event. Sourcing a bespoke piece for it perked my interest. Was it commissioned specifically or perhaps reworn from a private event? I’m curious. 

Taylor has also worn custom Monse to the 2024 MTV Video Music Awards. Monse is founded by Laura Kim and Fernando Garcia, the former creative directors at Oscar de la Renta - another brand Taylor has worn and loved for years. Indeed, there’s a Spring 2019 dress from ODLR that has elements of this Monse piece. The Resort 2027 collection, which this design appears to riff on, marks the pair’s renewed vision for their brand since stepping back from the storied American label in September 2025. 

A current best guess at Taylor’s much-requested necklace she wore during the TEU concert series this week! According to WWW Jewels, this DLNLX crystal choker originally debuted in December 2016 in a small 31-piece collaboration with the fashion retailer Nordstrom.

The piece was not included in credits shared by Taylor’s stylist, Joseph Cassell, of her ensemble - typically an indicator that the item in question is of personal provenance. But an item of this age is an older pull. If that is the case, I wonder when Taylor might have acquired it!

In either instance, the fabulous piece was an edgy complement to Taylor’s custom Monse dress. I personally liked the clean lined juxtaposition of the choker with the strapless silhouette.

Styled with another pair of Aquazzura stilettos, I could see this ensemble working beautifully for a red carpet. The “Taylor” touch of that shimmering crystal-embellished trim looked great under the stage lights and I thought tied in well with the silver accessories of country singer Lainey Wilson who Taylor joined on stage to close out the evening. 

TEU is now in its sixth year, having been organized by George Kittle, Travis Kelce, and Greg Olsen since in 2021. 

Attending Tight End University | Nashville, TN | June 22, 2026 

Simkhai ‘Lydia Jacquard Mini Dress’ - $495.00  Kindred Lubeck custom engagement ring Cartier ‘Love Unlimited Bracelet’ - $9,400.00 Aquazzura ‘Tequila Sandal 105 in Yellow’ - $1,635.00 

For a second year in a row, Taylor attends Tight End University. The annual event, shortened to TEU, gathers tight ends from across the league for a week of events ranging from training, to bonding, to a musical event. 

This is Taylor’s second year attending TEU. You might recall when Taylor attended last year she wore a charming greeeeeeeeeeeen gingham set by Hunter Bell. This year, she opted for a sweet yellow jacquard mini dress for another “Blondes In Yellow” moment following that lovely Oscar de la Renta performance gown she wore to the Toy Story 5 premiere. The pattern and sheen on the fabric of her Simkhai dress reminds me of the vintage-tinged dresses she’d most often reach for in the RED era. Indeed, that red lip completes the picture! What brings it to the present are those fun crystal heels which coordinate in shade to her dress. Taylor has worn a few Aquazzura pairs in recent outings, but this particular style might look especially familiar as she wore the bronze version to a wedding in New York in May. 

The concert portion of TEU is to be held tomorrow (June 23). Might she reprise last year’s performance? We’ll find out! 

Out and about | New York City, NY | June 15, 2026

Guest In Residence ‘Pique Polo Cashmere Top’ - $295.00 Chloé ‘Large Penelope Leather Shoulder Bag’ - $3,300.00 Kindred Lubeck custom engagement ring Darlene De Sedle ‘Crystal Opal Bracelet’ - no longer available Darlene De Sedle ‘Opal Ring’ - no longer available Cartier ‘Love Unlimited Bracelet’ - $9,400.00 Gucci ‘Horsebit Platform Sandal’ - $1,240.00

We are so back. Following a busy week last week (a movie premiere, basketball game, milestone career achievement, Broadway play), Taylor showed no signs of stopping this week when she was spotted in New York City heading into Electric Lady Studios - a recording spot favoured by her. What could she be working on? I look forward to learning more!

For her outfit, a cute short-sleeved sweater and jeans is given a more intentional touch with the coordinating brown accessories. The power of sandwich styling! Her sweater is by a brand she’s worn on a number of occasions for their comfy, elevated knitwear and happens to be owned by one of her closest friends: Gigi Hadid.

On the accessory front, Taylor rewore a few recognizable pieces from her jewelry box. Including her iconic opal jewels by Darlene De Sedle, once famously owned by Elizabeth Taylor. You may recall she wore the complete parure of this set while attending a wedding in NYC last month.

The bag, of course, is what captured my attention. From what I could see, anyway! At this glance, it tentatively another Chloé piece! I have a soft spot for the French brand and have always hoped Taylor would wear more pieces from them. This bag marks two occasions in a row as Taylor also carried one of their “bracelet” bags while attending the Broadway play “Oh, Mary!” over the weekend. I loved the repeating motif of warm, brown tones throughout this outfit - it made for easy roaming of the eye and pulled everything nicely together.

Attending "Oh, Mary!" on Broadway | New York City, NY | June 13, 2026

Ralph Lauren ‘Velvet Scoopneck Tank Dress’ - no longer available Chloe ‘Bracelet Leather Hobo Bag’ - $2,355.00 Three Stories Jewelry 'Horsebit Chain 16"' - $3,540.00 Michael Anthony ‘Moon Goddess Necklace Pendant’ - no longer available Foundrae ‘Diamond Initial Pendant’ $1,800.00 Danes Road Antiques 'Antique 18K Opal Bracelet’ - no longer available Kindred Lubeck custom engagement ring Aquazzura ‘Lovestruck Sandal’ - $1,710.00

What a full - and varied! - week of events for Taylor. We started things off with a film premiere and performance, then onto an excited courtside basketball game, a momentous milestone career award, and finished off with a Broadway show! While a rich velvet like this Ralph Lauren tank dress is perhaps an unseasonal choice for a balmy summer night, I did like the idea that it tied into a theatre’s velvet curtains. That color is beautiful! Plus, I felt the beautiful jewelry stacking added to the artistic vibe. To that, we saw a few repeats in Taylor’s array of choices, including a familiar ‘T’ necklace and a vintage opal bracelet we first saw her wear for an appearance on Colbert in December 2025. The Aquazzura sandals might also be striking a familiar note as they bear a similarity to the other Aquazzura pair she wore to a New York wedding last month.

But my favourite accessory detail was her bracelet bag by Chloé - a brand I have a personal soft spot for. What a thrill to see her carrying them. Its “bracelet” moniker almost ties into the jewelry styling, too!

Attending Songwriters Hall of Fame | New York City, NY | June 11, 2026

Givenchy custom Mindi Mond 'Imperial Citrine Earrings' - $19,000.00 Amrapali Jewelry ‘Ruby and Diamond Ring’ - price available upon request Jessica McCormack ‘Signature Diamond Button Back Bracelet’ - $91,000.00 Givenchy 'Satin Ankle Strap Sandals' - $1,355.00 (similar)

Taylor made history as the youngest female artist to be inducted into the Songwriters Hall of Fame upon her first year of eligibility. That she did so in a gown designed by one of the most admired female creative directors at a major fashion house - a rare breed in and of itself - felt like an added power statement atop the achievements both Taylor and Sarah Burton of Givenchy - formerly beloved at Alexander McQueen - have to their names. Add to the fact that Givenchy is a label I’ve had on my personal “Wi$h Li$t” for Taylor and I am delighted, to say the least, that she wore them for the very first time on a red carpet.

With three collections under her belt at the French firm, the fashion community widely appraised Burton’s FW2026 offering as her best yet. What made it particularly poignant was her candor to speak about designing clothes for women and the emotional facets that underpin the act - not just simply the logistics of construction. “It’s very personal,” Burton said during a press preview of the show. “In many ways, it’s about how you put yourself back together in a world that’s falling apart.” Adding, “It’s how to address all those elements of being a woman and how to navigate that. How do you speak to all those different emotions and different experiences?” That description easily overlays atop another artist’s very personal body of work. One which has become, for millions, a backbone of maneuvering a uniquely feminine emotional landscape.  

In addition to her standout citrine earrings (as a November baby - I swooned), Taylor styled the rest of her jewels rather simply with just a cocktail ring and a single bracelet. Some might say that the strapless dress presented an opportunity for a statement necklace. I admit I’ve always loved the restraint of a bare neckline (I opted for one at my wedding - also with a strapless dress). Although, a multicolored gem necklace could have made for a very lovely “eras”-like nod as she accepts such a milestone achievement that reflects on two decades of songwriting. As a minimalist ankle-strap lover, I’ve been in heaven these last few appearances. While I tend to gravitate toward a slightly less square toe shape, TSSers thoughtfully pointed out how the shoe shape echoes that of her strapless dress. A mirroring effect I fully support and love hearing from this observant community! All in, simple felt like the right route to take as it gave more emphasis over to the stunning embroidery of that dress.

In the 20th year of her career, it feels like Taylor is being given her flowers by the industry in the form of milestone accolades. Her place on NYT Mag’s 30 Greatest Living Songwriters list and her induction into the Songwriters Hall of Fame seem like just the start. So why not embody that gesture sartorially, too? Her black satin crepe gown cut a timeless silhouette, featuring a tailored bustier and slit  - a look Taylor has favoured in recent years. Its uniqueness came from the richly sprawled floral and butterfly embroidery, each bloom conceivably an emblem of the color coded eras that define the discography the evening was in celebration of. To be sure, one of my first visual connects was to the piano from the Eras Tour which Taylor sat behind to play songs pulled from every corner of her catalogue. It’s beautiful, personal, and - dare I say - a fashion hall of fame moment, too.

An additional congratulations to Taylor’s team and the incredible work they’ve done so consistently for so long: Joseph Cassell, Jemma Muradian, and Lorrie Turk.

Spurs at Knicks | New York City, NY | June 10, 2026 

Alana Haim x Gildan custom tee - $2.99 Area ‘Slit Jeans’ - $495.00  Dior ‘Small D-Motion Bag’ - $4,000.00 Versace 'Embellished Sandals' - no longer available

Taylor attended Game 4 of the NBA Finals tonight with longtime friends Alana, Danielle, and Este Haim. Taylor has attended multiple Knicks games over the years from as early as 2014 to as recently as last month when she saw them play the Cavaliers on their home turf in Cleveland, OH with Travis. At that previous game, she opted to not put her team loyalty on display. Not so here! In full Knicks (ahem, Stevie Knicks) regalia, she made it clear who she’s rooting for. The girls of Haim were also in on the fun as they wore matching tees that played on Knicks puns. (Alana in “Knickelback", Este in “Knickole Kidman”, and Danielle in "Knickolas Cage"). The Cut confirmed that the tees were the handiwork of Alana Haim who has been known to rock some conversation-starting custom tees. Alana later spoke to Vogue where it was confirmed that the tees were purchased from Michael’s at $2.99 each, then custom screen printed with punny plays on the Knicks by Alana herself. In the piece, Alana expresses her longtime love of merch and shirt making for friends. The “Stevie Knicks” phrasing was Taylor’s idea. “We really just wanted to have fun, because we were so excited that we were going to the game, and I thought it would make people laugh,” said Alana.  As for the question of how Mariska Hargitay got her hands on one? “I always bring extras,” said Alana.

Besides her repeat Dior bag, the item that of course stood out to me immediately were her jeans! They should be familiar to anyone who’s observed Taylor’s sporty playbook. They’re by the brand Area. Taylor has worn their cheekily iconic crystal-embellished denim on a number of past occasions to take in other sports. Most memorably at Super Bowl LVIII when the Chiefs beat the 49ers in an overtime clincher.

Performing at Toy Story 5 premiere | Los Angeles, CA | June 9, 2026

Oscar de la Renta ‘Porcelain Flower Embroidered Sleeveless Gown’ - $8,990.00 Alder Fine Jewelry ‘Pear Diamond Drop Earrings’ - $6,000.00 Anabela Chan ‘Daisy Earrings’ - $2,385.00 Ldezen ‘Pink Fifi Earrings’ - $4,000.00 Nadri Jewelry ‘Macaron Yellow Cushion Pendant’ - $80.00 Jimmy Choo ‘1998 Leo 65 Sandal’ - $925.00

Once inside the Dolby Theatre, Taylor had an outfit change for a touching performance with Toy Story soundscape legend: Randy Newman. Taylor to delivered the first live rendition of her original song for the film “I Knew It, I Knew You" then came together with Newman to duet “You’ve Got A Friend In Me."

Taylor swapped out her Erdem mini for a yellow gown by Oscar de la Renta. Where Taylor has never previously worn Erdem to a red carpet event, ODLR is a recognizable go-to designer for her. Besides greeeeeeeeeeeen, I’ve always fostered a secondary soft spot for Taylor in yellow. The yellow hue makes an obvious tie into the iconic typography of Toy Story, the flowers continue the evening’s soft and sweet vibe, and sparkles will always be an excellent choice to shine under a stage spotlight. Additional floral clips were entwined into her hair which was let down from the red carpet’s half updo style into a loose romantic plait. The styling choice had me thinking of Rapunzel - perhaps another nod within the animated Disney universe and to amplify the soft “princess” energy. Among her other jewels she swapped out from her red carpet look includes a high/low moment between a diamond drop pair of earrings by Alder Fine and an $80 yellow CZ pendant by Nadri Jewelry that played with the colour of her gown nicely.

Rounding out the last of Taylor’s performance accessories! For her hair, earrings were creatively repurposed to be used as clips pinned almost Rapunzel-style into her braid. I thought the styling choice completed the “Disney princess” effect of it all and also gave a subtle tie-in to her pink-toned lip. 

Then, *just* spotted during her piano performance of “I Knew It, I Knew You” a gold pair of Jimmy Choo sandals. The year in the style name had me scurrying to check when the original Toy Story was released (1995). What a great nod that would have been! Instead, this collection was actually an homage to Sex and the City - a revival of select Carrie Bradshaw-approved styles from the famed series. Taylor’s style here is a lower version rendered in metallic gold of the leopard print pair Carrie wears during the iconic opening credits (picture that famous tutu and tank top caught in the spray of a passing bus!). 

Attending Toy Story 5 | Los Angeles, CA | June 9, 2026

Erdem Fall 2026 Antique Necklace Le Vian ‘Fancy Yellow Diamond Earrings’ Selim Mouzannar ‘Gemma Ring’ - $4,410.00 Kindred Lubeck custom engagement ring Miraki Jewelry ‘Oval Tennis Bracelet’ - $2,080.00 Aleví Milano ‘Bar 110 Sandals’ - €670,00

Taylor at the world premiere of Toy Story 5 in Erdem. Her original song for the film, “I Knew It, I Knew You”, broke records upon release as the biggest soundtrack single based on first-day plays.

As always, I had initial opinions when I first saw photos of Taylor. Then came the thoughts that benefited from a closer look. Among my surface-level takeaways was what a playful homage the dress is to the landscape of Toy Story. It’s a little Western (perhaps a nod to Jessie, the character who inspired “I Knew It”) and a little whimsical yet sweet - fitting for a family film. There’s also a nod to Taylor’s magpie tendencies; has she ever met a sequin she didn’t love? Styling-wise, I’m a sucker for a bow and a minimalist sandal, both of which get checks from me. A half-updo, minimal jewelry, and a plait keep things relaxed and unfussy. The shoes are also a new-to-Taylor brand. Where I typically would have expected standbys like Jimmy Choo or Giuseppe Zanotti to be at play for a red carpet look, we instead get an introduction to Aleví Milano. While a powder blue or metallic silver hue might have been more expected, I thought the warm tan shade of her heels grounds the look and, perhaps I’m reaching, felt like a strappy stiletto way of nodding to a pair of cowgirl boots.

Diving deeper, Taylor’s dress comes from Erdem’s Fall 2026 presentation titled “The Imaginary Conversation.” Created for the house’s 20th anniversary, Erdem Moralıoğlu conceived the collection as a “dialogue” between Erdem’s muses. That conversation is woven into the looks through richly textured brocades, florals, and frayed edges. Moralıoğlu described the concept as a “mashup” rather than a retrospective, thoughtfully revisiting Erdem house codes through his signature romantic lens.

Several parallels caught my attention. Wearing a dress celebrating 20 years of Erdem to an event positioning Taylor’s return to her country roots feels like an apt bookend as her career approaches the 20th anniversary of her debut album this fall. It’s the second time she’s recently nodded to a 20th anniversary, following the Stella McCartney x H&M top she wore to a Cavaliers game last month. Toy Story 5 also arrives in theatres on June 19 — the 20th anniversary of her first single, “Tim McGraw.”

The idea of a mashup also brought me back to The Eras Tour. The show itself was a supercut of Taylor’s past eras, but its most literal mashups came during the acoustic set, where Taylor paired songs from across her catalogue to deepen old stories and create new meaning. That same connective spirit feels echoed in the dress’ patchwork details which brings contrasting fabrics together into a cohesive whole and also nods to the (presumed vintage) jacket from the “I Knew It” visuals.

Attending Knicks at Cavaliers | Cleveland, OH | May 23, 2026

Stella McCartney ‘Denim Jacket’ - $1,990.00 Stella McCartney x H&M ‘Chain Tank Top’ - $169.00 Dior ‘Cigale Bag’ Kindred Lubeck custom engagement ring Tiffany & Co ‘Diamond Wire Ring in Yellow Gold’ - $3,450.00 Jacquie Aiche ‘Large Marquise Diamond Pave Signet Ring’ - $8,045.00 Stella McCartney ‘Wide-Leg Jeans’ - $790.00 Stella McCartney ‘Elsa Sandals’ - $1,404.00

Turns out, they both know how to ball — and Aristotle. Taylor joined Travis to take in the Cavaliers wearing a look that struck the perfect balance between cute and casual for a sporting event. Jeans and a “going out” top: the infallible millennial outfit formula. 

It also seems there was plenty in that recent Stella McCartney delivery to Taylor’s NYC apartment, as this marks her third ensemble from the British designer in a week. Taylor and McCartney’s creative history runs deep. Starting from their pastel dreamscape Lover merch collab in 2019 to McCartney outerwear appearing on the covers of folklore and evermore in 2020. Here, Taylor wore an almost entirely McCartney look courtside. Much of it is from the Spring 2026 collection, alongside one piece from McCartney’s newly revived H&M collaboration which appears to reference McCartney’s iconic “Falabella” chain motif. It, alongside Taylor’s other black pieces - including those strappy sandals which had my minimalist strappy sandal loving heart swooning - grounded the wide legged denim jeans she wore. Those jeans also got a callout through her bomber jacket, which featured a denim back pocket motif on its back. Cheeky! It speaks to Taylor’s long friendship with Stella to give her collection a nod and also makes for a fun high/low moment. Indeed, H&M is known for their approachable price points and special designer collections. In Fall 2005, McCartney was tapped as the brand’s second-ever designer collaboration. She returns to the retailer for a second round some 20 years later. Both collections were released to huge sellout success. 

For jewels, Taylor went simple. Including two pieces from her jewelry box that are repeats from Tiffany and Jacquie Aiche. But the accessory that spoke to me most was the bag. Since taking the helm at Dior, Jonathan Anderson’s work has been met with acclaim. To be sure, Taylor has now carried six Anderson-designed bags in the last month. It’s rare that Taylor participates in “it” fashion in this way - her style more often creates trends than follows them - but Dior’s new “Cigale” bag, Anderson’s debut original design for the firm, makes a compelling case for exception. As a lover of bows, I gasped! To Vogue, Anderson described its namesake, Dior’s 1952 “La Cigale” dress, as his “favorite dress of all in the history of fashion.” The structured silhouette and bow-front detailing cleverly reinterpret the original cocktail dress into a handbag. La Cigale (Jonathan’s Version), you could say.

To me, there’s a lovely bit of poetry in Taylor wearing two fashion stories. One, a 20 year revival. The other, an original debut. But that could just be my debut-loving heart in an admittedly sentimental mood given her eponymous first album approaches its own twentieth anniversary this fall. 

Attending a wedding | Glyfada, Greece | May 9, 2026

Zimmermann ‘Rebellion Embellished Dress’ - $1,915.00 Steven Battelle Jewelry ‘Ancient Coin Necklace’ - no longer available De Beers ‘Arpeggia One Line Earrings’ - $29,500.00 Reformation ‘Waldena Block Heeled Mule’ - $268.00

A big month for weddings! Earlier in May, Taylor and Travis attended the destination wedding of George Karlaftis, Travis’ teammate on the Chiefs, in Greece. And once again, Taylor turned to a beautifully embellished midi dress by Zimmermann. You may recall she wore a cream floral midi dress by Zimmermann to another wedding she attended with Travis: that of Electric Lady Studios’ owner Lee Foster and Karen Elson in New York City back in September 2024.

While not quite the fabulous suite of jewels we saw her wear at last weekend’s wedding in New York, Taylor’s earrings are a recognizable favourite from her jewelry collection. She first wore them to the 2024 Golden Globes and has repeated them on multiple fancy occasions. The coin necklace is also a repeat from her jewelry box, first worn during the Chiefs 2025-26 season (she has a few of these ancient coin pieces in her collection). It almost feels like a nod to the steeped history of Greece.

Between the whimsical mermaid pattern on her dress and the “shell” like quality of her heels, I also got the Mediterranean vibes from her ensemble. Again, perhaps a nod to the Greek locale! Continuing to prove Taylor’s thoughtful approach to dress, even as a wedding guest. Between the two of them, these are brands Taylor continues to turn to over the years. The added bonus of styling them together is the fun high/low the two of them make!

Attending a wedding | New York City, NY | May 16, 2026

Maria Lucia Hohan ‘Allar Cutout Gown’ - $2,280.00 Darlene De Sedle Opal Earrings - no longer available Darlene De Sedle ‘Crystal Opal Bracelet’ - no longer available Darlene De Sedle ‘Crystal Opal Marquise Bracelet’ - no longer available Darlene De Sedle ‘Opal Ring’ - no longer available Kindred Lubeck custom engagement ring Aquazzura ‘Ari Clutch’ - $1,795.00 Aquazzura ‘Tequila 105 Crystal Embellished Sandals in Brass’ - $1,635.00

Taylor and Travis appeared as guests at a wedding tonight in NYC! Taylor’s beautiful pleated full-length gown was an immediately recognizable one to me as Taylor has worn this designer before. First, many years ago in 2012 in the “Begin Again” music video. Then, more recently, at the “15 and Mahomies” gala in 2024. Such is the benefit of having a signature style - it’s that distinctive! While the gown is described as “gold” - which Taylor accessorized with via her coordinating Aquazzura bag and heels - it also sort of has an olive green sheen to it don’t you think? Or perhaps I should say … greeeeeeeeeeeen.

Meanwhile, on the jewelry front, Taylor took the “Elizabeth Taylor” route by committing to wearing the full vintage opal suite by jeweler Darlene De Sedle that recently came into her possession. The earrings, bracelets, and ring all once belonged to the famed actress who purchased many of De Sedle’s pieces in the late 90s. This is our first time seeing all of the pieces worn together. Taylor has previously been spotted accessorizing outfits with the bracelets and ring separately. The earrings, worn for a more festive occasion out, give us the debut reunion of all the pieces together on Taylor. How stunning!

The Florida-based jewelry retailer Fox Estate Jewelry provided additional background on the timeline of events that led to Taylor acquiring this beautiful suite of opal jewelry. Following the Christie's auction of Elizabeth Taylor's jewelry collection in 2011, Fox Estate acquired the suite. Fox Estate told WhoWoreWhatJewels that they sold the set around Christmas 2025 for a “six figure deal” to “a sports agent.” It appears that now we’re seeing the fruition of that sale! While not directly confirmed as a gift from Travis, it at least goes without saying that this suite would be a very thoughtful gift to Taylor. Its provenance in Elizabeth Taylor’s personal jewelry collection and its material composition of opals are both of massive significance to her.

Out and about | New York City, NY | May 15, 2026

Dôen ‘Ashlynn Dress’ - $348.00 Gerard Darel ‘Archie Raffia Chain Strap Shoulder Bag’ - $375.00 (no longer available) Jacquie Aiche ‘Rose Cut Round + Marquise Finger Bracelet’ - $5,791.00 Kindred Lubeck custom engagement ring Darlene De Sedle ‘Crystal Opal Bracelet’ - no longer available Aquazzura ‘Twist 95 Soft Raffia Mules’ - $495.00

What a week of looks! Taylor headed out to dinner tonight, this time with Travis, in NYC.

Her dress extended her current neutral streak and also harkened back to the darker take on florals she wore while out with Travis in London last week. While that dress, by Zimmermann, had a corseted bodice, Dôen’s view on florals (for spring!) is much softer thanks to smocking and a cotton composition. It’s a very Dôen dress if I’ve ever seen one: Sweet, romantic, and lightweight. Taylor has previously worn dresses of theirs similar to this. They make for such an easy and breezy option as the weather warms.

If I had to describe her previous looks from a wider lens, they all appear to carry an elegant, sophisticated feel. This dress is sweeter, perhaps even familiar, by contrast. Taylor has always loved a cute dress!

Leaning in closer to glimpse the details, I was drawn to the thoughtful interplay of her accessories - some old, some new. Her Gerard Darel bag, for instance, is an older piece in her collection that she first debuted back in 2023. She coordinated its texture neatly to her - new - Aquazzura heels which were also made of raffia. Such great picks for spring/summer! Her Jacquie Aiche hand jewelry, another older item from 2023, picked up on the chain detail of her bag. And, might I say, gave this softer look an unexpected and fun oomph. Meanwhile her Darlene De Sedle opal bracelet, an heirloom piece that originally belonged to Elizabeth Taylor and that we first saw her wear last month, picks up on the floral print in her dress (Perhaps a reach?)

What are your thoughts on this look?

Out and about | New York City, NY | May 14, 2026

Stella McCartney ‘Poplin Peplum Top’ - $1,190.00 Fendi ‘Peekaboo ISeeU Petite Bag’ - $4,500.00 Cartier 'Love Unlimited Bracelet' - $9,400.00 Cartier 'Santos Demoiselle Watch' - $18,330.00 Kindred Lubeck custom engagement ring The Row 'Virgil Pleated Pants' - $1,335.00 The Row 'Awar Leather Sandals’ - $850.00

Another day, another sighting! This brings me back to a time, way back in 2014-15, when not a day would go by without Taylor getting spotted on the streets of New York displaying her fabulous street style. Although what makes this an extra special treat? Seeing her in trousers! I feel like it’s a rare moment to see Taylor looking so tailored - pun intended. 

Indeed, if you look at Taylor’s latest string of outings, a pattern appears to emerge. As a lover of restrained neutrals and sharp minimalism, it’s a noticeable aesthetic shift that I’m swooning over. To be sure, celebrity style is at its most effective when consumed in aggregate, not in isolation. Styling is a skill - it’s not just simply picking pretty things. Taylor - and her longtime stylist Joseph Cassell - knows this well. Her last few street style ‘fits all appear to build on one another in color, silhouette, and mood. This takes the other day’s coordinating black accessories and neutral-toned separates into a more suit-forward direction. I’d copy and paste this outfit in a heartbeat! 

This outing also possibly answers tabloid speculation from this morning when security was spotted arriving at Taylor’s NYC apartment carrying a Stella McCartney-branded garment bag and tote. Perhaps inside that delivery was this very chic ensemble? 

One final note? As a millennial, I wasn’t quite prepared for the peplum top renaissance!