21.Jess Day's plaid coat with skinny jeans tucked into knee-high boots from New Girl.
Poor Jess never stood a chance because, in her defense, Nick never explicitly called their dinner a date. Regardless, trying to match a baseball tee with leather boots is bold even for the quirkiest girl in Los Angeles.
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.
19.Sally Albright's big-shouldered blazer and creamy blouse from When Harry Met Sally.
For how often Meg Ryan is praised for her iconic movie outfits, surely Sally had better items in her wardrobe than what she pulled out for this double date. This blazer is way more "hire me at your Fortune 500" than "let's fall in love."
18.Pam Beesly's corporate cardigan over a striped button down shirt from The Office.
I know Pam isn't known for her style, but pairing this monochromatic blue look with a pink coat is giving cotton candy vibes (and not in a good way).
17.Donna Pinciotti's red, silk blouse from That '70s Show.
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.
16.Alison Scott's loose-fitting tank top and ponytail from Knocked Up.
After their wild night at the bar, Alison asks Ben to a formal dinner and shows up in underwhelming V-neck sweater. Her accidental first date outfit was much more fun if you ask me.
15.Polly Prince's T-shirt, jeans, and boots from Along Came Polly.
There has to be a better way to demonstrate a free spirit than a wrinkled scarf. And I understand she's supposed to have eclectic taste, but front-facing jean pockets?!
Reuben looks like he's ready to meet the parents, whereas Polly looks like she's late to first period.
14.Tiffany's lace-sleeved top with jeans from Silver Linings Playbook.
It's not hard for Tiffany to look good on a first date opposite Pat, who literally wears a garbage bag for a large portion of this movie. Even so, I could have done without the gothic cross necklace.
13.Sasha's flannel and overalls from Always Be My Maybe.
Extra points go to Sasha for rocking Doc Martens and fishnet stockings while losing her virginity in the back seat of a car.
12.Rachel Green's brown, velvet top and high-waisted slacks from Friends.
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.
11.Lorelai Gilmore's deep, ruffly V-neck shirt with boot-cut jeans and sandals from Gilmore Girls.
The velvet jacket adds a nice touch of texture to an otherwise simple look. It's not jaw-dropping, but this look is just right for a cozy and romantic small-town meal.
10.Summer's embroidered button-up dress from 500 Days of Summer.
Everyone's favorite “manic pixie dream girl” certainly wowed Tom with this delicate dress. I think it's perfect, if not even too formal, for a daytime Ikea date.
9.Kate's black dress and minimalistic necklace from Baby Mama.
Kate also nailed the outerwear on this date with an understated coat and striped scarf. She looks put together and ready to land a second date.
8.Sara's sporty chic Jet Ski outfit from Hitch.
I'm a big fan of the metallic purse paired with a form-fitting and intricately designed top. If the costume designer was going for the cool girl next door, they aced it.
7.Michelle Robinson's peach blouse, knee-length cream skirt, and small, leather purse from Southside With You.
Unsurprisingly, one of America's most fashionable First Ladies was also great at dressing for dates. The color of the blouse makes the whole outfit pop, and I will definitely be shopping around for her dainty leather bag.
6.Cher's strappy white dress from Clueless.
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.
5.Angela Moore's funky-patterned green dress and choker from Boy Meets World.
The half-up hairdo and choker were a perfect balance to this busier dress. I would personally feel comfortable wearing this outfit to a fancy restaurant or even a dive bar, so major points for versatility.
4.Kat Stratford's effortlessly cool long-sleeve tee paired with platform flip-flops from 10 Things I Hate About You.
Kat's outfit change into a white jumpsuit (which was quickly destroyed by paint balls) was also a smash hit. There's no need for expensive dresses or high heels when you have as much chemistry as Julia Stiles and Heath Ledger.
3.Anna Scott's high-waisted jeans paired with a tank top under an embroidered, silk jacket from Notting Hill.
Despite being an A-list actor, Anna shows up to a quaint dinner party in jeans and a plain top. As a result, she fits in with her date's friends beautifully.
The jacket adds the right amount of texture and pattern to an otherwise simple outfit. So the ensemble is not only cute, but also weather appropriate for a quiet evening stroll with her babbling beau.
2.Carrie Bradshaw's “naked dress” under a knee-length fur coat from Sex and the City.
Mr. Big clearly enjoyed the slip dress because the couple didn't make it from the limo to the restaurant before he took it off.
1.And finally, Céline's grungy tank dress accessorized with an oversized flannel and black backpack from Before Sunrise.
There is no denying that Céline radiates main character energy in this dress. It looks like she threw these items together without thinking, which only adds to the ensemble's appeal.
Plus, when things get steamy for the couple as the date goes on, Céline peels off the T-shirt layer. There are so many possibilities for styling these items, which makes this the perfect outfit for the ever-so-unpredictable first date.
