10 Dresses Taylor Swift Wore During Her Fearless Era That I Wish I Had For My 16th Birthday

Getty / Jon Kopaloff

In the name of nostalgia, and obviously because Taylor Swift is rerecording her Fearless album, I couldn’t help but fall into the rabbit hole of all the sparkly minidresses she used to wear with cowboy boots. This is partly because she dedicated her hit “Love Story” (Taylor’s Version) to her fans and released a montage video with her favorite photos from that time period.

Right around then, I was attending Sweet 16s and trying to collect as many sparkly dresses for these parties as I could. I would have given anything for just one of Taylor Swift’s red carpet numbers, which were by the likes of Collette Dinnigan and Naeem Khan, and always, always paired with Christian Louboutin peep-toe shoes, when they weren’t cowboy boots. Taylor had all the essentials, from embellished Jimmy Choo clutches (perfect for holding Juicy Tubes lip gloss) to sparkly guitars that matched with her metallic shifts. What would I have done with the guitar? IDK, probably nothing, but I would have definitely made use of those clutches.

All of this is to say that Taylor’s red carpet outfits from 2008-2009 are worth looking back on if you, too, wish you could turn back time and look just a little bit cooler; a little bit more fearless at any event you attended back then. Ahead, see my top 10 favourite minidresses Taylor Swift wore during her Fearless era.

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