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Swift’s personal style has, not surprisingly, matured over the course of her career, migrating from the early days of sundresses and, as she describes them, “bedazzled cowboy boots” to the vintage fifties vibe of a few years ago to the sleeker, street-conscious look she favors now. “I can look back at an old photo and tell you roughly what year it’s from,” Swift says. “Going through different phases is one of my favorite things about fashion. I love how it can mark the passage of time. It’s similar to my songs in that way—it all helps identify where I was at in different points of my life.