Favourite Outfits of All Time: Taylor Swift Style

With this year being truly the first where Taylor has purposefully avoided the spotlight (despite releasing her latest album), I had to figure out a way to continue my year-end tradition of compiling my favourite outfits of the year. As there were so few outfits to choose from, I decided to follow through on an extremely popular request: My favourite outfits of all time. As I’m sure you can imagine, though I’ve been requested to do this many times, it’s always a daunting task just to try and pick my favourite outfits from over the course of a year. Let alone trying to whittle that down into my Top 10 (or in the case of candids, Top 30) for every category over the course of more than a decade. But while this took some time, I hope it encourages some discussion and of course flashback and love for how Taylor’s fashion has continued to grow and change over the years! 

I hope you guys enjoy them — see some of your favourites, see some that surprise you, and that you all discuss your own favourite outfits that you think should belong here!

Thank you to everyone who has supported Taylor Swift Style not only through the years, but during this year in particular. There hasn’t been a lot for me to post fashion-wise so I appreciate so many of you still checking out TSS and being so supportive!

Fingers crossed that with 2018′s tour, we’ll have many more outings of Taylor as she continues to explore her reputation style.


Favourite Outfits of All Time: Events

In looking back over my Top 10 event choices, I’m actually extremely impressed with myself at the diversity of brands I’ve included here and that there isn’t one single repeat (with the exception of an event repeat, if you want to count that). 

I also unintentionally have put together an even split between neutrals and colour. Obviously, my love affair for green is in full force here as I couldn’t not include her adorable Miu Miu number here as well as my love for blondes in yellow being seen in that elegant golden Jenny Packham full-length gown. 

Her VSFS after-party look in couture Zuhair Murad and her flawless Alexandre Vauthier appearance at last year’s VF Oscar party should surprise no one as both of these looks were also received by TSS-ers with widespread acclaim. But, some may be most surprised by my inclusion of such an inconspicuous and plain vintage LBD. But the styling is what has always cemented that look in my Top 10. The inspiring decision to pair the vintage frock with an ultra-modern PVC pair of studded Louboutins was the perfect contrast, in my eyes. 

What do you think? Are any of your favourites here? 


Favourite Outfits of All Time: Awards

In making this list, I very quickly realized that Taylor had a serious winning streak at the ACMs, since I included three outfits on this list of only 10 from that award show alone. 

I also want to specifically point out her dove grey tulle gown from the 2011 CMAs — an extremely underrated outing that doesn’t get nearly enough love. The wispy, soft grey alone is such a quietly stunning colour that she rarely ever wears as she usually opts for black or white or metallics — all of which are also seen here. 

My love for green and yellow both come into play, as well as a white hot streak — all of which set themselves apart thanks to impeccable styling. The 2012 ACMs for their beyond perfect hair and makeup, the 2012 MTV VMAs for its suit silhouette, and the 2013 People’s Choice for those earrings. 


Favourite Outfits of All Time: Photoshoots

Pulling together this list was actually quite easy as, looking back, there were so many photoshoots that I’ve subconsciously added to this list in my mind and have loved for so many years it was easy to pull them out. For instance, that Marchesa moment in her Marie Claire 2010 spread, the white Chloe dress from her 2014 Glamour shoot. And, of course, her completely epic and amazing shared shoot with Karlie Kloss for Vogue in 2015. 

One of my favourite things about photoshoots is that it’s essentially like Taylor getting to try on couture costumes, expand her range, and seeing her professionally photographed in ensembles, hair, and beauty that we would ordinarily never get to see her in. I always applaud experimentation in photoshoots, which might be why some of you might be surprised by the addition of her Harper’s Bazaar Germany shoot on here as there were a few unorthodox style choices in there. But ones that I loved seeing Taylor in! 


Favourite Outfits of All Time: Candids (1/3)

My all time favourite candids has been one of my most-requested features since starting TSS. And if I have had trouble narrowing down my favourite candids on a yearly basis, trying to create a list that spanned a decade of fashion was … well. It took me a long time. 

In doing this list, I also realized just how many outfits from the Speak Now era I love. It’s possible that I’ve never realized until now that … maybe the SN era is one of my favourite eras of style? Instead of even attempting to order this list by my love for the outfit, I’ve gone chronological. Also because I think that adds an extra bit of interest to the list as you’re able to actually see Taylor’s style change and grow over time. Which fascinates me endlessly. In the above, you’ll see her move through the preppy looks from the Speak Now era and transition into the vintage-inspired styles of RED (more to come in part two). 

Throughout this list, you’ll probably see a few reoccurring trends that I love: knee socks, leather jackets, neutrals, unique colour combos, small pops of colour (usually green or yellow), and stripes. 

Are any of your favourites on this list? 


Favourite Outfits of All Time: Candids (2/3)

In addition to ordering everything chronologically, for TSS-ers fan of the City Theory, I’ve also included all of the cities from my favourite candids as well for you to keep track of her style geographically. Obviously you’ll note the increase of NYC candids thanks to the New York City Fashion Takeover in 2014. 

More things worth noting: The transition from oxford flats to ankle boots to heels as the 1989 era style really started kicking in. 


Favourite Outfits of All Time: Candids (3/3)

Note the added amount of heels in these ensembles, the raised hemlines, and the chic-er fits. Taylor’s style over the last few years has definitely grown up with her. 

One thing that hasn’t changed is my love of green (hello, Elie Saab bag), neutrals (those beautiful graphic Alice + Olivia shorts and white hot Rachel Zoe romper) and leather (check that Blaque Label skirt). 

And yes, I’m equally as shocked as you to include two outfits from the exact same day as some of my favourite outfits Taylor has ever worn over the course of her entire career. But, can you blame me? I know some people hate coats being worn as capes, but I think it’s a chic way to style a look, plus the monochrome flip between the two outfits. 

There were only 30 outfits included on this list, whittled down from a decade of fashion. And I still had 14 more outfits on stand-by that I had to runner-up remove from this list. 


Favourite Outfits of All Time: Tour

It’s funny, because over the years I’ve been asked plenty of times about my favourite and least favourite outfits. But it’s not until you really sit down and try to look at an entire body of fashion that you realize the trends and similarities that bubble up to the surface. 

Like who knew that the 1989 Tour had my favourite wardrobe of all her tours? Or that as much as I am RED AF forever, turns out, I really wasn’t a huge fan of the costumes she wore on that tour. There were actually a few more outfits from the 1989 Tour I could have included here, like her famous white co-ord and thigh highs ensemble by Jessica Jones. But I thought having literally half the list be from one tour was a little much.  


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