Favourite Outfits of 2019: Taylor Swift Style

It’s funny writing this intro and reflecting on last year’s (and even the year before that) and the one constant: I wish I had more material to work with. 

Last year I had predicted a new album would be unleashed upon us and with it, hopefully, an onslaught of promotional imagery and outings akin to the great New York Fashion Takeover we were gifted during the 1989 Era. In looking back, I don’t think we quite hit that mark. 

To me, this era was Taylor’s most fashionably inconsistent. There was almost a marriage between the pastel rainbows and summer festival scenery Taylor wanted to embody on Lover with the edgy OTK boots and dark palette of reputation — plus a string of fantastic menswear outfits. 

I noted last year that the juxtaposition of snake imagery with sparkly kaleidoscopic dresses was the perfect representation of the two combating narratives on reputation: The perceived image the public saw weighed against the privately held love story that was unfolding in her quiet reality. With Lover we’ve seen many battling images. The spillover of reputation’s snake colliding with the butterfly of Lover ultimately crashed into the aesthetic of a businesswoman seeking to establish herself as an icon not just of the year but of the decade. We were met with sharply tailored two piece suits and blazers as she openly discussed the sexism and toxicity of the industry she has experienced as a young female to a successful grown artist — owning her work, her imagery, and the legacy she has built. It’s an incredibly appropriate end to a decade. 

TSS won’t quite be hitting a decade of documenting Taylor’s style (that’s in 2021!) but, as always, I want to thank anyone who has ever liked, reblogged, commented, messaged, and as of a few months ago supported the Taylor Swift Style Patreon. Your words, your dollars, your silent contribution to this community is more than I could have ever fathomed and I’ll spend many decades feeling so grateful I ever had the opportunity to write intros like this. 

With that. 

Let’s get started. 


Favourite Outfits of 2019: Taylor Swift Style

Award - MTV Video Music Awards

In making a choice between Taylor’s two incredibly similar printed suit Versace moments from 2019, the clincher was the shoes. And I am simply not one to turn down a pair of OTK boots. 

The hits of black, the restraint on pattern, and the green (!!!) earrings all also deserve shoutouts as reasons for my choosing the MTV VMAs lewk over the Teen Choice Awards. It altogether felt like a more polished and mature outing (which makes sense given the other award show was literally packaged for teenagers). 


Favourite Outfits of 2019: Taylor Swift Style

Award - American Music Awards

… And to absolutely no one’s surprise, a green red carpet outfit made it onto the end of year list. 

You all knew this was coming. 

There will be no explanation there will only be TAYLOR SWIFT IN GREEN. 


Favourite Outfits of 2019: Taylor Swift Style

Event - Time 100 Gala

I won’t be doing a Favourite Outfits of the Decade series (I only very recently did a Favourite Outfits of All Time list only two years ago here). But if I were to do so, this look would have a fighting shot at being included as one of Taylor’s all time best. 

Though it’s sad that this sherbet moment of boho goddess goodness did not repeat itself consistently throughout the Lover era — at least lightning got to strike once. 

The pale pink colour, the floral headband, the glowy makeup, the custom bolero that absolutely makes the outfit (Joseph *chefs kiss* truly) and the shot of lemon yellow at the side panels. True dreamy perfection. 


Favourite Outfits of 2019: Taylor Swift Style

Event - Billboard Women In Music

I believe I myself said it best when I said: “Everything about this, to me, feels modern and elegant and age appropriate.”

The braided ponytail, while contentious, felt fresh and fun to me. As did the asymmetric chain detail at the neck and loose fit on the pants (I have been burned too many a time already by overly tight jumpsuits and rompers from Taylor thank you very much). I will always be in love with a strappy sandal, especially when it’s perfectly coordinated to the metallic hits in the rest of the outfit. Including a continuation of Taylor’s style team this era selecting some of the best jewelry I’ve noted in Taylor’s career. The Dream Team have really been having fun with swirling ear cuffs and unique stacking ring choices that I, for the first time, am avidly really following her jewelry game and enjoying it so much. 


Favourite Outfits of 2019: Taylor Swift Style

Performance - Tiny Desk

Everything about this look paid perfect homage to the Lover era. The heart embellishments on the blazer, the matching pantsuit, the rich pink/purple hues. I swoon. 


Favourite Outfits of 2019: Taylor Swift Style

Performance - TMall Double 11 Gala

I continue to expose myself as a sucker for OTK boots. 

At least I’m consistent. 

I loved the embellished print, the tie belt, and the shirt dress-esque silhouette. As mentioned, I feel like I prefer this looser look on Taylor compared to some of her too tight (imo) looks from this era. Like the Wonder Woman Versace corsetry and Femme Beetlejuice romper lewks. 


Favourite Outfits of 2019: Taylor Swift Style

Candid - February 10

The coat makes it a candid. 

With so few outings to choose from, I’m forced for a second time in FOOTY history to select a cheat moment — a coat thrown on top of a red carpet look. The first being this Louis Vuitton moment from 2016. 

A sweetly monochrome Cinderella-worthy look. That blue wool coat is stunning. 


Favourite Outfits of 2019: Taylor Swift Style

Candid - April 24

  • Zadig & Voltaire jacket
  • N:Philanthropy tee
  • One Teaspoon shorts
  • P448 sneakers
  • (posts on lockdown and not linked)

The candid that actually encapsulated the summer festival and pastels of the proposed (as yet unknown) Lover era. 


Favourite Outfits of 2019: Taylor Swift Style

Candid - May 25

Candids were, let’s say, limited this year. But at least we had the sunshine of this Blondes In Yellow™ look to contribute. Technically this barely counts as a candid (I’m cheating) because she’s captured on her way to a press interview. But with so little to hold onto, I’ll make it count. 

The sweet French twist updo, floral print, and coordinating ankle strap yellow heels were all lovely touches to this feminine outfit. 


Favourite Outfits of 2019: Taylor Swift Style

Photoshoot - Lover

Dreamy pastels, unique set ups, and fun clothes. The ethereal looks from Taylor’s album photoshoot for Lover is up there amongst my favourite album photoshoots Taylor has ever done. (For the complete order of that, head here). 


Favourite Outfits of 2019: Taylor Swift Style

Photoshoot - Vogue UK

Everything in this spread was … scrumptious. I loved every last detail. Including the frosted 90s supermodel lips and retro flicked hair. 

Also green boots.


Favourite Outfits of 2019: Taylor Swift Style

Photoshoot - Billboard

I accurately summed it up when the cover of this shoot was released. If there was a way to sum up the Lover era in fashion … a “bright pink ruffled cotton candy gown, belted by a thick heavy black belt and finished off with an oversized blazer” was sure to do it. 


THEME