"New York is one of those cities worth dressing up for. When I walk onto the sidewalk I want to try a little harder," Swift explained to Seth Meyers after he confronted her with a series of post-workout paparazzi pics on The Late Show in August. Forgoing the season's "athleisure" trend, the impeccably dressed singer stepped out in posh frocks that included a navy-and-white wool check ensemble straight off the Oscar de la Renta runway and a below-the-knee floral cocktail dress that recalled the glamour of Grace Kelly.

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