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Taylor Swift Style Turns Ten 10×10: Candids

This was, undoubtedly by sheer volume, the most difficult category of all of them to parse through. After going through some 1,100 appearances spanning 13 years worth of street style moments I somehow managed to narrow it down to my Top 10 (very painfully, might I add).

Organized by month of appearance.

January 21, 2014: Lanston tee / Reformation skirt / Dolce & Gabbana bag / Rag & Bone booties. All black, a blazer, with a pop of colour (in my power colour red, no less). Everything about this outfit still holds up after all these years. And I also love her loose carefree waves.

February 24, 2016: Isabel Marant blazer and trousers / A.L.C. top / Manolo Blahnik pumps. How could one ever forget Taylor’s sensational string of Isabel Marant ‘fits in early 2016? This white hot monochrome suit was only just caught by cameras, but it still holds a firm place in my heart for its aching chicness.

March 29, 2014: J. Brand jacket / Cuore & Pelle bag / Rag & Bone booties. This outfit is timeless and is basically how I dress in the Pacific Northwest for at least half the year. That leather jacket is enviable.

March 30, 2014: Anthropologie bag / Paige pants / Isabel Marant booties. Yes this is definitely an unintentional record for proximity to all time favourite outfits. But I couldn’t shake the impeccable layering and colour palette here. It’s a well-coordinated, office-friendly look that doesn’t rely on just basic black which I applaud.

April 28, 2015: Missguided blazer + shorts / Lulufrost necklace / Elie Saab bag / Prada pumps. I think it’s pretty evident why this lewk made it into the top 10. Everyone, say it with me: Greeeeeeeeeeeeeeeen. The masterful accessory matching to really bring a fun bounce of spring into an otherwise neutral matching set is genius and so fresh. I’d absolutely wear this in a heartbeat.

May 26, 2015: Swarovski sunglasses / Zara top / Mary Katrantzou bag / River Island shorts / Pedro Garcia heels. This outfit absolutely snuck up on me and is part of the reason why I noted “being open to having your mind be changed” at the introduction of this series. While I certainly liked this outfit six whole years ago, it never made a lasting impression on me. In fact I’d say if you’re a longtime reader of TSS that of the top 10 you see here, only this one should be a surprise. But upon reflection in thinking of all my criteria: Actual street style, memorable, impeccably styled with zero changes I’d make … Undoubtedly this moment fills all of that criteria for me. The artful way the shoes tie in to the bag, the sunglasses tie in to the top and shorts, the sleek deep-parted hair, and red/pink lipstick that also ties into the bag. This is a moment where intention was evident and Taylor looks supremely confident in that smirk and that strut. I absolutely have to give kudos to how well this outfit speaks to every single element present here. It’s a fact I’ve always known about Taylor but was never more evident than when I had to pare outfits down and really began to split hairs that she does not always nail it in the accessories department, to the detriment of the outfit as a whole. In the instance of my entire Top 10 but especially here I feel that intentional styling was evident to bring the whole outfit into cohesion and clarity. Well done.

July 15, 2018: Elie Saab sunglasses / Faith Connexion dress / Stella McCartney bag / Jimmy Choo boots. A WHOLE ASS SERVE. I have no other words. This was impeccably styled by Taylor’s longtime stylist Joseph Cassell who saw a slouchy floral shirt dress and envisioned a 70s chic power moment. I know it’s evident by the fact that it’s here but I really need to shout from the rooftops how this is absolutely one of her best street appearances of all time and every single person alive should know it.

August 13, 2010: Urban Outfitters bustier + bag + skirt / Anthropologie ring + belt. There are some people who say to not mix black and brown which I find ridiculous. A careful mix of neutral tones (black + white + brown) is one of my favourite things to do and I love the feminine layers at play here, anchored by a chunky equestrian-esque belt.

October 23, 2016: Meshki coat / Vatanika bandeau / Giuseppe Zanotti clutch / Melinda Maria ring / Blaque Label skirt / Christian Louboutin sandals. This outfit still leaves me speechless and shooketh to my core. I truly don’t know what I could possibly add to this outfit that the outfit doesn’t say on its own as to why it deserves to be here as one of her most memorable street style moments.

November 22, 2011: Ralph Lauren sweater / Fendi bag / Modcloth skirt / Marc Jacobs heels. Completely flipping gears … This outfit. Pure nostalgia. And it’s very appropriate to round out the Top 10 with this particular outfit. If you’ve been following TSS since this moment just … wow. Wowowow. All my heart love and soul and feelings go out to you. This was the first street moment outfit that I found on my own with no press credits or designer notes guiding my way. This was the first time as I embarked on learning how to run a style blog that I felt, “Oh. I can do this, can’t I?” It was such a momentous occasion for me that still gives me all the feelings of validation and pride and my first real boost of confidence and joy that this blog was doing something to me internally and giving me something I had never had before. The final piece of the puzzle I believe was finding the Marc Jacobs heels. That rush of serotonin? Can’t replace it. I also recall spending so. much. time. trying to find that Fendi bag. And it was all mine. Sentimentality aside, this is Taylor artfully playing with an untraditional and unexpected colour palette. Which is one of her best skills in fashion, imo. Nothing about this should work. And yet it’s absolutely charming and evokes all the feelings of fall for me.

What do you think of my Top 10 candids, TSSers?