I agree with the poster who said the vintage look was right for her. She was an artistic person, working in a classy store that sells high quality clothes, but she's on a tight budget, so the vintage choice would be the best solution. Also, the dresses were understated in a way that went with her problems with depression, and her Vermont upbringing.
However, Ray saw something more vibrant in her, and she LOVED the things he bought for her, the red dress, the lilac flowered one, the evening gown, and she looked like a different person in them. I thought they expressed the side of her personality he was trying to bring out, and she was responding to that.
Then at the end, she appears at the gallery with Jeremy in a real knockout dress that could have been from a vintage store (especially in Los Angeles) but not necessarily.
She has the looks that would make a pair of overalls look good, but I thought the clothes were definitely used to express the relationships in this movie.
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