- “Gossip Girl” ended nearly a decade ago, but its fashions are still relevant and trendy.
- Insider spoke to two stylists and had them rank characters’ looks from least memorable to most iconic.
- Stylists liked Vanessa Abrams’ style but felt it was forgettable.
- Blair Waldorf, Chuck Bass, and Nate Archibald all earned high honors for their wardrobes.
- Both experts agreed that Serena van der Woodsen’s style deserved top marks.
- Visit Insider’s homepage for more stories.
“Gossip Girl” ended nearly a decade ago, and it is still considered to be one of the most stylish shows of all time — but which character is the real Queen Bee when it comes to fashion?
To figure out who deserves a spot at the top, Insider consulted Vanessa Menendez, a celebrity stylist and fashion historian based in Miami, Florida, and Jené Luciani, a style consultant and published author based in upstate New York.
Here’s a ranking of “Gossip Girl” characters’ style, from least memorable to most iconic.
Celebrity Fashion: Vanessa’s style was low-key and often forgettable.
When Vanessa Abrams shows up during the first season, she’s just returned from living with her sister in Vermont for a year. And even though she, like Dan, grew up in Brooklyn, Menendez finds her to be the least quintessentially “New York” of the characters.
“Let’s just say…. ‘small-town girl living in a lonely world’ replays in my head,” Menendez said, speaking of Vanessa’s fashions.
And although she wasn’t poorly dressed by any means, Vanessa had some questionable and forgettable outfits.
“Her Vermont look is ever-present throughout the show. Vanessa isn’t one for high fashion or bold looks, she likes to play on the fact that she’s a small-town girl who doesn’t care about money,” she added.
Celebrity Fashion: Lily may not be the biggest fashionista, but her style still wins points.
Lily van der Woodsen (formerly Lily Rhodes and Lily Bass), is positioned as the former “It Girl” who has mostly retired from the spotlight by the time her kids are in high school.
But that doesn’t mean Lily’s not stylish — Luciana said she admires the simplicity of her looks.
“Lily was the classic mom we all aspire to be: elegant, sophisticated, and chic. Definitely still relevant for today,” she added.
Celebrity Fashion: “Underestimated hipster” Dan consistently wore stylish, casual looks.
Dan Humphrey may be at the bottom of the Upper East Side food chain, but his style actually translates really well.
Menendez praised Dan Humphrey for his cool, outsider look.
“He’s just got that handsome, mysterious, grunge look to a T. His style is smart and sexy, a reader-writer vibe. He can pull off oxfords, relaxed-fit jeans, a basic tee, and vest like no one else,” she told Insider.
Celebrity Fashion: Jenny earned respect from both experts.
Jenny Humphrey starts off the series as an unsure high-school freshman who is trying to find her footing on the Upper East Side, but she eventually becomes a total style icon who knows what she wants.
Menendez told Insider that Jenny’s style was probably the most dynamic of the whole cast.
“One of the most evolved characters if you ask me. She starts out with an innocent, quirky, and preppy look,” she added. “She later finds a style all her own, and with her natural-born creativity, stemming from her ex-rockstar dad and artist mom, it’s no wonder she broke out of her shell.”
Luciani said she also admires Jenny’s DIY-style approach to fashion.
“Jenny was the cutting-edge girl — trying to keep up with the others, but didn’t have the budget so she made her own,” she explained.
Celebrity Fashion: Georgina made an impression with her dark, rocker style.
Both fashion experts commented on Georgina Sparks’ dark, bad-girl style, befitting of the recurring villain’s conniving and chaotic behavior.
“When the rest rocked bright colors, Georgina brought it back down to reality with her all-black ensembles — after all, this was New York City,” Luciani told Insider. “Biker jackets with fringe, studded boots, and tons of accessories piled on at once were her style staples.”
Menendez praised Georgina’s dark, neutral color palette as well.
“She’s extra chic in blacks and grays, playing with jewelry in the same color schemes, layering necklaces with cross embellishments, and rings. She’s elegant in a mysterious ‘Don’t mess with me’ kind of way,” Menendez added.
Celebrity Fashion: Blair made an impact on the fashion of the mid-aughts.
Menendez described Blair Waldorf’s style as “Parisian Prep,” always put-together with a romantic, European spin on prep-school chic.
“She loves to look prim and polished — you may never see a hair out of place,” she explained. “Blair adds her own touch of Paris chic, with her love of stockings, headbands, cardigans, and a classic mini pump.”
Luciani also pointed out Blair’s penchant for strong looks, like bold prints, silhouettes, and accessories, even while remaining polished.
“Whatever trend she tried, she brought it to the extreme. That made for lots of drama, and not just in the storyline,” Luciani told Insider.
Blair also made a major fashion impact with her iconic headbands — she made them a trendy statement piece of the early 2000s.
Celebrity Fashion: Menendez ranked golden boy Nate as her favorite of the guys.
Nate Archibald takes the preppy vibe of the Upper East Side and puts his own romantic, sensitive spin on it.
And even though many of his looks are understated, Menendez said they stand out and hold up.
“He has an effortlessly cool style,” Menendez told Insider.”Nate is edgy but oh-so chic. Button-ups (not tucked in) with blazers and loafers are Nate’s best look.”
Celebrity Fashion: Chuck also received high marks from the stylists.
Luciani said Chuck Bass has the second-best style on the show, giving the brooding bad boy points for always looking polished and dapper.
“I love a good scarf and Chuck was the king of the scarf,” she told Insider.
Menendez also agrees that his signature accessory seals the deal: “The scarf is Chuck’s signature. It’s not true ‘Chuck Bass’ fashion if it doesn’t have a scarf.”
“He loves a good suit, paired with the right button-up, vest, tie, belt, cuff links, and dress shoes. He loves to layer and [he] does it oh-so well,” Menendez added.
Celebrity Fashion: Both experts agree that Serena’s style deserves top marks.
Both Luciani and Menendez said Serena van der Woodsen was their top pick in terms of fashion.
“She’s the most in line with high fashion and the biggest risk-taker,” Luciani told Insider.
Menendez described Serena’s look as “rebel princess,” adding that her style is effortless and bold.
“Her party-girl past is always present even in her finest looks, from wearing her prep-school ties undone to mixing sequins in her black-tie-affair, or even daytime, looks. Her style is extremely bold, gutsy, edgy, and says ‘Here I am’ in the most effortless way possible,” she told Insider.