I want to see what Ted sees in Robin, but I'm distracted by this utterly boring blouse. This outfit reveals nothing about her character, especially for a first date in a pilot episode!Robin's outerwear and black purse are more sophisticated, but not enough to forget what's underneath.Columbia Pictures
I know Pam isn't known for her style, but pairing this monochromatic blue look with a pink coat is giving cotton candy vibes .It's a nice blouse — it really is. Yet it's much too mature for a high school student to be wearing on a first date. Donna's usual getup is much edgier, so I say it's fair to expect more.Ben and Alison meet during a drunken night and spend the evening dancing and eventually fall into bed together.
Extra points go to Sasha for rocking Doc Martens and fishnet stockings while losing her virginity in the back seat of a car.It's a lovely, albeit bland, ensemble from fashion-forward Rachel Green. Yet she probably knew that after decades of pining, Ross didn't need her to show up in anything flashy.Gilmore GirlsLorelai, aka queen of early '00s fashion, toned down her usual funky patterns and bright colors for her first date with Luke.
Kate scares her first date away by revealing she's 37 and looking to start popping out children. But her simple, yet elegant dress would've been enough for me to hear her out. I cannot think of a more stylish high school student. And it was an absolutely iconic move to toss on this sheer"coat" when her father told her to cover up before leaving the house. Cher was fighting against dress codes long before it was cool.Buena Vista Television
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