We gave the iconic Serena van Der Woodson and Blair Waldorf's outfits a 2021 upgrade

Dress like your favorite Upper East Sider this summer

Actresses Blake Lively and Leighton Meester on location for "Gossip Girl" on March 14, 2008 in New York City.
(Image credit: James Devaney/WireImage)

Hey Upper East Siders, your favorite gossip-filled show is about to get a reboot later this year, but while we wait for the new series to air, it's time to pull out your most chic Gossip Girl styles as we prepare to welcome New York's most elite back to our television screens.

The original Gossip Girl may have ended in 2012, but it left behind a legacy of TV style icons. Serena Van Der Woodsen and Blair Waldorf's outfits were showstoppers throughout the series and left a lasting impression—just look at Blair's signature headbands, which are making a serious comeback this season.

Blake Lively and Leighton Meester on location for "Gossip Girl" on June 25, 2008 in Port Washington, New York.

(Image credit: James Devaney/WireImage)

Even though it has been almost a decade since Gossip Girl was last on-air, the fashion still has some influence today. Y2K styles including denim on denim, low-rise cut bottoms, and rectangular-shaped sunglasses have also started making a comeback, making this the perfect moment to bring back some of our favorite Gossip Girl styles.

Amanda Gorman's inauguration look is just one instance where we see the Gossip Girl legacy leaking into this year's fashion trends. Prada debuted a Blair-like padded headband back in 2019, but once Amanda wore the look during the inauguration, it proved that headbands are officially back in style. The poet sported a statement red Prada headband paired with a bright yellow tailored jacket that even Blair would probably approve of.

National youth poet laureate Amanda Gorman arrives at the inauguration of U.S. President-elect Joe Biden on the West Front of the U.S. Capitol on January 20, 2021 in Washington, DC.

(Image credit: Win McNamee/Getty Images)

In anticipation of the reboot, fashion brand Alice + Olivia are also rolling out a Gossip Girl-inspired collection that is giving us all the nostalgic feels. Whether you're looking for some trendy school girl-inspired fashion or if you're finally ready to unleash your inner Blair Waldorf style, we've found the most stylish Gossip Girl-inspired styles that are 2021 approved.

Blair Waldorf Outfits

Leighton Meester on location for "Gossip Girl" on November 26, 2007 in New York City, New York.

(Image credit: James Devaney/WireImage)

Our favorite It girl Blair Waldorf was known for making a statement during the series. Though not all of her outfits may translate to today's style, you can still take some elements from her Y2K looks and make them your own. 

Academic looks played a crucial role at the start of the series and pieces like her noteworthy headbands, collared shirts, and statement jackets are outfits you can still pull off today.

Leighton Meester on location for "Gossip Girl" on July 7, 2008 in Port Washington, New York.

(Image credit: James Devaney/WireImage)

Comfort has taken a front seat this year with clothes, making anything tight and restricting a no-go (after all, we've been relying on our working from home clothes for way too long). Blair is known for inserting elegance into practically every look she wears, and these pull-on shorts are no exception. With button-downs and blouses taking center stage this season, don't play it safe with basic colors and prints. Just like Blair, add some pop of colors to your outfits, and don't be afraid to incorporate some textures too.

Leighton Meester on location for "Gossip Girl" on June 25, 2008 in Port Washington, New York.

(Image credit: James Devaney/WireImage)

A staple summer dress is a must-have in your wardrobe, and who better than Blair to inspire some chic fits? This year, florals and bold colors have become super popular, so make a statement this year with a vibrant dress perfect for weekend brunches.

Serena Van Der Woodsen Outfits

Blake Lively is sighted on location for 'Gossip Girl' on July 5, 2010 in Paris, France.

(Image credit: Trago / Contributer / Getty Images)

Serena also served some killer looks throughout the series, bringing us more glam and casual looks to wear in most places. Her style can still be seen today, especially as monochromatic and neon colors take over the runway.

Rather than add accessory after accessory, fashion today focuses more on pairing basic pieces with a couple of accessories, like a purse and hat for a more put-together look. 

Blake Lively is seen on movie set of 'Gossip Girl' on March 27, 2012 in New York City.

(Image credit: ANDERSON/Bauer-Griffin/GC Images)

Bold and vibrant colors are in this year, so definitely don't shy away from any neon shades. Serena's confidence was basically its own character during the series and she wasn't one to tone down her looks. To turn the above photo into something more 2021 appropriate, trade the black and green combo for a simple flowy dress and pair it with a cute pair of neon heels.

Penn Badgley and Blake Lively on location for "Gossip Girl" on the streets of Manhattan on July 15, 2008 in New York City.

(Image credit: James Devaney/WireImage)

Along with athleisure taking over the fashion world, tie dye has quickly risen to the top of the best patterns to wear this season. Serena showed off a tie dye casual tank, which would be perfect for this year's style. Whether you're running errands or lounging on the couch, tie dye adds an interesting and unique look that is perfect alone or as part of a matching set.

This summer, let your inner Gossip Girl style out and start bingeing the show in preparation for the reboot coming to us later this year on HBO Max.

Rylee is a U.S. news writer for woman&home and My Imperfect Life who primarily covers lifestyle, celebrity, and fashion news. At times, she also reports on beauty, royals, entertainment, health, and travel. The latest fashion and beauty trends, along with any quirky travel destinations are her favorite topics to write about. 


Before coming to woman&home and My Imperfect Life, Rylee originally studied journalism at Hofstra University where she explored her interests in world politics and magazine writing. From there, she dabbled in freelance writing covering fashion and beauty e-commerce for outlets such as the TODAY show, American Spa Magazine, First for Women, and Woman’s World.


When she’s not writing articles, you can find her testing out one of the many restaurants New York City has to offer and planning her next travel destination. Her other hobbies also include hiking, ballet, yoga, and reading practically any book TikTok recommends.