Darling are you a nightmare dressed like a daydream and by any chance, is your dreamy outfit inspired by any of our fashion ladies? We’ll find that out soon enough because this time, we have decided to talk fashion. Whoever knows Hollywood, knows how these two go hand in hand (by making sure the accessories match).
Celebrities have inspired a lot but if there is one thing to pick with the most impact, for me it would be fashion. Who doesn’t remember the moment when Rachel walked in her runaway bridal gown, that alone made many weddings happen. Not to forget the iconic little black dress that left the kind of imprint on the entire Hollywood that it still refuses to go out of style. In the history of Hollywood, we have no scarcity of fashionistas, but to keep our list readable we’ll take a dive into the wardrobe of these top 10 iconic characters ruling the Pinterest boards.
Related: Hollywood’s Top 10 Fashion Icons
1. Lorelai Gilmore – ‘Gilmore Girls’
Let’s start with the best (no offense to Rachel) Lorelai Gilmore from ‘Gilmore Girls‘ was Mother before the term made it out of the old period dramas and took a spot in Gen Z vocabulary. This innkeeper Barbie was styled by the brilliant Brenda Maben and she made Lauren Graham’s character of Lorelai – who are two of the same people in my expert opinion – come to life in vibrancy. Brenda put a little blend of vintage finds and contemporary pieces and staged them on lovely Stars Hollow gal.
With her eclectic wardrobe and signature bandanas, Lorelai embodied bohemian chic with that dash of small-town charm. From her iconic graphic T-shirts and denim essentials to her desperate coffee runs, Lorelai’s laid-back style that somehow always looked perfect captured so many eyes. To count some of the iconic looks we have her dropping Rory off to Chilton look, God knows why everyone had to make the poor girl feel awkward over that. She definitely aced the hot mom test on the first day of school. Mama Gilmore’s turtle neck and leather jackets with those signature cowboy boots are something to die for, if you don’t agree, we’ll know your closet is stuffed with beige M-fitted blouses you never seem to match your shoes with.
2. Rachel Green – ‘Friends’
Could we be any more excited to talk about the ultimate ’90s fashion icon, Rachel Green? Styled by the fabulous Debra McGuire, Jennifer Aniston‘s Rachel in ‘Friends’ revolutionized the way we view fashion on television. From her classic pieces to her iconic haircuts, Rachel’s effortlessly chic style is still going strong in 2024.
Whether she is getting coffee that’s not even for her or rocking a sleek pencil skirt at the office, her fashion-forward choices continue to top the trend charts just like the show itself. Rachel Green’s style is something that isn’t just reserved for millennials, take a step out and look at the Gen Z’s with their crop tops claiming our dear Rach as their spirit animal. ‘Friends’ fashion sparks that nostalgia for the glory days of ’90s trends and as Taylor Swift said herself, they come back stronger.
3. Serena Van Der Woodsen – ‘Gossip Girl’
XOXO, Upper East Siders! It’s finally time to step into the glamorous world of the golden princess Serena van der Woodsen, the reigning queen of Manhattan chic! Styled by the incomparable Eric Daman, Blake Lively walked in Serena’s shoes like they were custom-made for her (they probably were). It’s not news that ‘Gossip Girl’ captivated audiences with its high upper-class New York fashion looks, but Serena particularly had the most enviable wardrobe.
From her glamorous gold-dipped gowns to her casual-cool looks accommodating her hobby of having to leave at any important moment made her the IT girl of a territory spreading far beyond the borders of the Upper East Side. With her perfectly polished yet messy golden hair and that permanent tan paired with those never-ending legs, Serena could wear a rag and make that look like the next Versace collection piece. After all, it was Blake Lively under all that glamor, it had to glow extra brighter.
4. Blair Waldorf – ‘Gossip Girl’
Bow down, Upper East Siders, because Queen B is here to reign supreme! Another queen styled by none other than legendary Eric Daman. Leighton Meester’s as Blair Waldorf is what you call a perfect casting decision. While S was all gold and messy, B was about tight curls and polished shoes. She dazzled audiences with her sophisticated style and impeccable taste, which paid her off in the long run as well, we wouldn’t have expected anything less from a fashion designer’s daughter.
Blair’s signature headbands and pearls with that preppy-chic twist on her school uniform were the ultimate Upper East Side elegance. She’s the kind of fashion friend you’d want to have for her knowledge on the subject remains impeccable and she has that Queen command that one can’t deny, I swear I’ve never worn tights as pants since B very intensely told not to. Waldorf fashion is classy, timeless and the the kind that never goes out of style.
5. Cher Horowitz – ‘Clueless’
As if we could forget about the fabulous Cher Horowitz! Styled by the visionary Mona May, Alicia Silverstone playing Cher in ‘Clueless,’ was a cultural shift moment. This twisted retelling of Jane Austen’s ‘Emma’ brought ’90s fashion to the forefront with those preppy-chic fits and coordinated sets. Yep, no one is forgetting Cher’s iconic app that paired the iconic yellow two-piece set for her school. From her plaid skirts to her knee-high socks and fuzzy pens, Cher’s wardrobe was the perfect blend of high fashion meets high school.
Cher was a trendsetter before it even was a thing and we’re betting our brains that in today’s age and time, she would’ve been a fashion influencer. You are the spokesperson for yourself but I’ll be in the corner snapping selfies from the back camera of my flip phone channeling my inner Cher Horowitz, because why wouldn’t I want to?
In case you missed: Kim Kardashian Leaves Balenciaga Tag Hanging Out From Her Dress During Paris Fashion Week
6. Carrie Bradshaw – ‘Sex And The City’
If I had $40, I would spend it on shoes as well because the queen of Manhattan Ms Carrie Bradshaw did it as well. Sarah Jessica Parker as Carrie Bradshaw made many of us fashion girlies feel seen with her crazy obsession with all things stylish. Stylist Patricia Field’s one of the most iconic creations is still standing tall on the steps of Met. There’s no doubt that ‘Sex and the City’ revolutionized the way we view fashion on television. Carrie’s daring couture ensembles and eclectic mix of high fashion to vintage finds make her the perfect fashion idol you can follow blindly.
Whether she’s strutting down Fifth Avenue in Manolos or rocking a tutu on the streets of New York, Carrie’s iconic looks have left an indelible mark on the fashion world of television. If you can get those signature curls and balance that statement jewelry, why would you want to buy dinner anyway? Vogue would be enough. So grab your Cosmopolitan and get ready to take a walk in Carrie Bradshaw’s fabulous shoes!
7. Holly Golightly – ‘Breakfast at Tiffany’s’
Oh dear darling, you thought we forgot about the epitome of elegance and sophistication, Ms. Holly Golightly. Not a chance. Styled to perfection by the legendary Hubert de Givenchy, Audrey Hepburn in that little black dress of Holly in ‘Breakfast at Tiffany’s’ set hearts aflutter and fashion trends ablaze. She started a fire so big, it’s still flaming up the walls of many.
From that iconic little black dress to the oversized sunglasses and not forgetting that cigarette case in her tiny little hands, Holly’s wardrobe remains eternally iconic. Her timeless looks in the 50s classic continue to inspire designers and fashionistas alike to this date.
8. Samantha Jones – ‘Sex and the City’
Sex, sass, and style—oh my! Let’s talk about the fabulous Samantha Jones, another fashion lady from ‘Sex and the City.’ Styled by once again, Patricia Field and played by Kim Cattrall, Samantha was a character that put her unapologetic approach to fashion out of display like the baddie that she was. Taking in her curve-hugging dresses, power suits and killer heels, that wardrobe was a celebration of confidence and femininity.
Sam’s fearless attitude was one of her most iconic accessories that she wore with every outfit without fail and that is what continues to inspire women to embrace their inner goddess and strut their stuff. It’s a grab your stilettos and dance around till they break time, because honey, you’re fabulous!
9. Elle Woods – ‘Legally Blonde’
Who says you can’t be smart and dressed like an icon? Well, whoever did, make them watch Legally Blonde because our favorite law student Elle Woods needs to have a conversation. Styled by Sophie de Rakoff, Reese Witherspoon’s vibrant and feminine look in this comedy has become a timeless feminist piece with its witty dialogues and even wittier outfits. From Elle’s pretty pink fits to her designer accessories along with her bubbly personality and that glimmering high IQ brain, there wasn’t anything her wardrobe was lacking.
Elle Wood’s fashion in ‘Legally Blonde‘ was a celebration of girl power and self-expression. She was our Barbie before Margot Robbie convinced Greta Gerwig to make one and for that time, we’re grateful. Her iconic pink outfits and determination to succeed fed us enough to apply to Harvard Law and get a chance to say “Is that hard?“
10. Phoebe Buffay – ‘Friends’
The quirky fashion sense of iconic Phoebe Buffay remains the most real representation of New York’s street fashion. No, we’re not talking about the Upper East Side of those shiny streets of Manhattan, we’re talking about the real NYC, carefully created by stylist Debra McGuire.
Lisa Kudrow as Phoebe was another perfect cast call but her iconic long shirts and bohemian jewelry made her the perfect downtown girl. Describing her wardrobe in one word is a task so we’re giving it as many as we can fit in a line, funky, vibrant, antique and free-spirited, just like her personality.
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