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Taylor Swift Style Turns Ten 10×10: Awards

Red carpet moments are one of the most fun parts of TSS – documenting Taylor at her most glamourous in designer ‘fits is a rush like no other. Since 2006, Taylor has attended approximately 117 award shows.

In order to make it all the way down to just ten lewks I had to be super choosy and nitpicky – just wait for the candids list to see how hard that was.

Organized in chronological order.

2010 Academy of Country Music Awards: Marchesa gown / Neil Lane Jewelry / Christian Louboutin heels. This lewk is still just as delightful now as it was on Taylor over a decade ago. This enchanting light purple colour, the way the appliques move from one shoulder to its opposite bottom corner to falls in a way to keep your eye moving and is beautiful. The softly curled updo (a go-to of early days Taylor) and simple drop diamond earrings were lovely and soft finishing touches.

2011 Academy of Country Music Awards: Elie Saab gown / Neil Lane jewelry. We all know I can’t resist a Blondes In Yellow™ moment. Nothing about this appearance is overcooked in any way. The tumbling softly brushed out curls, the minimal makeup and jewelry. It allows the buttery yellow gown to shine and it offsets her skin really beautifully. Classy and understated.

2011 Country Music Association Awards: J. Mendel gown / Lorraine Schwartz jewelry. A criminally underrated lewk. I’ve always had a soft spot for the graceful and gentle dove grey gown Taylor wore to the 2011 CMAs. In part because we’ve never seen her after that in a colour quite like this on the red carpet. The pink lip brightens up what otherwise could have read as a somber grey gown.

2012 Academy of Country Music Awards: J. Mendel gown / Lorraine Schwartz jewelry / Christian Louboutin sandals. I still gush over this. Given the presence of three column gowns on this list I guess it isn’t a surprise that this is one of my favourite silhouettes on Taylor. Everything about this look from the smoky makeup, the ashy blonde hair, the gold accents, the modern cut outs, the crisp white all has me swooning. I think really it’s the hair and beauty that really send me over the edge.

2013 BRITs: Elie Saab gown / Neil Lane jewelry / Giuseppe Zanotti sandals. Another trend I’m noticing in these favourites is her full fringe and a polished blow out that draws me in. As I’ve mentioned, these lists are about head to toe perfection. Those shard drop earrings and how they tie in to the metallic accents of the belt and snaky sandals are beautiful and again keep the eye moving throughout the look. More smouldering makeup and a combination of a neutral with hits of gold has my full heart. She looked so hot here.

2013 NRJ: Elie Saab dress / Ofira + Lorraine Schwartz jewelry / Jimmy Choo sandals. Of all the lewks, this is the one that is likely the most surprising. But in going over her appearances that I loved, I kept coming back to this one and dubbed it as the best of her minis. The fit, the embellishments, the fun earrings, and perfectly selected sandals that mimic the texture of the dress. And again that smoky makeup and polished blowout combination I apparently find irresistible. This was a well-styled and signature sparkly Taylor in a gold or silver sparkly mini from head-to-toe.

2013 People’s Choice Awards: Ralph Lauren gown / Sutra earrings / Le Vian ring / Christian Louboutin pumps. Another underrated moment that is a prime example of how styling can elevate even the simplest of looks. This otherwise plain white plunging Ralph Lauren gown didn’t have much going for it until it was paired with stunning aqua earrings by Sutra, a teased updo to give that plunge nothing to compete with, and smoky brown shadow. This was a very mature and well-handled moment of what could have otherwise been an unremarkable gown.

2014 American Music Awards: Michael Kors gown / Chimento earrings / Le Vian + Casa Reale rings / Jimmy Choo sandals. I recognize that this may not be the most popular of my Top 10 choices but it’s the TSS Top 10 which means it’s mine damnit and I say Taylor Swift in gree(eeeeeee)n goes in the Top 10. I think my favourite styling moment is the way the cut of the ring mimics the shape of the illusion bodice. Otherwise, the playful bob and the excellent cut of this gown really allows the beautiful colour and modern cutouts to shine.

2014 Grammys: Gucci Première gown / Lorraine Schwartz jewelry / Jimmy Choo sandals. This Grammy look. Periodt. I’m obsessed with the tailoring of this gown, the execution of ‘sparkles’ that somehow feel more mature than her princess sparkle days of yore, the way the kicky ponytail prevents that mature take on glitter from aging her, the fresh pink lip keeping things from being too stale, the geometric diamond earrings mimicking the design at the collar and cuffs of the dress, and the smoky silver shadow to correspond with her silver gown. Plus that inner eye shadow pop! Perfectly done.

2019 MTV Video Music Awards: Versace blazer + bodysuit / Lorraine Schwartz earrings / Lorraine Schwartz + Ofira jewelry / Christian Louboutin boots. The appearance of this lewk in the Top 10 surprised me too but I guess that’s the power of a pair of thigh high boots and green earrings. I would go so far as to argue this is also her best appearance at the MTV VMAs. The chunky rings play in to the colours of the blazer and the overall proportions of the short blazer meeting the thigh high boots is fun and sexy and perfect for the award show at hand.

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