Madewell Just Created the ‘90s Capsule Collection of Your Deepest Tween Fantasies

Blake Lively (Serena van der Woodsen)

Of all the Gossip Girl cast alumni, Blake Lively is arguably the most well-known. Not only has she gone on to major roles in movies — including The Age of Adaline, The Shallows, All I See Is You, and most recently, It Ends with Us— but she's also married to fellow actor Ryan Reynolds (married in 2012).

Blake shares four beautiful daughters, James, Inez, Betty, and the youngest (born in 2023) whose name has not been announced publicly with Ryan. True to her Gossip Girl character, she's quite the fashionista! In her spare time, she likes to hang out with her BFFs, who just so happen to include Taylor Swiftandthe Sisterhood of the Traveling Pants ladies.

Leighton Meester (Blair Waldorf)

Leighton Meester has a career that would make even her cunningly ambitious Queen B character proud. Since Gossip Girl's end in 2012, she's acted in films including Life Partners, The Judge, The Weekend Away, and most recently, EXmas. She even recorded and released songs such as "Good Girls Go Bad" with Cobra Starship and the solo effort "Somebody to Love," and even starred on Broadway in Of Mice and Men back in 2014.

Leighton is married to actor Adam Brody (The O.C., Jennifer's Body, Gilmore Girls) as of 2014. She has two kids – one daughter and one son.

She has been heavily involved in philanthropy while taking on acting projects, primarily volunteering and campaigning with Feeding America and the Los Angeles Food Bank.

Taylor Momsen (Jenny Humphrey)

Long gone are the days when Taylor Momsen played Dan Humphrey's sweet (and a bit messed up) little sis, Jenny. The actress left the Gossip Girl cast in 2010 in order to pursue her dreams of a music career, and all these years later, she's still doing just that as the frontwoman of the uber-successful rock group, The Pretty Reckless. With four records under their belt, the four-member band has supported bands like Evanescence, Soundgarden, and Guns N' Roses, and has toured in numerous cities and music festivals.

Momsen has typically kept her dating life on the down-low. She is currently single and appears to be putting all of her energy into her band.

Penn Badgley (Dan Humphrey)

Everyone’s favorite Gossip Girl — er, guy — Penn Badgley, followed in his on-screen sister's footsteps after the show ended, pursuing his musical interests with rock band MOTHXR. The band's most current project, Centerfold, was released back in 2016.

Badgley has since acted in several movies and TV shows including Easy A, The Paper Store, and Here Today, but his most notable work has been on the ongoing book-based Netflix series, You. He plays Joe Goldberg, a charming bookkeeper with eerily odd characteristics, especially when it comes to love.

Badgley currently has a podcast titled Podcrushed, which explores the awkwardness of adolescence and revisits guests' best (and worst) middle school memories. He cohosts with Nava Kavelin and Sophie Ansari. One episode even features ex-Gossip Girl co-star, Leighton Meester!

Badgley is married to singer and doula Domino Kirke as of 2017. Kirke already had a child from a previous relationship. Badgley and Kirke had their first son together in 2020.

Ed Westwick (Chuck Bass)

Ed Westwick tapped into his angsty side post-Gossip Girl, starring as Tybalt in a 2013 adaptation of Romeo & Juliet. Since then, he has fought crime as Kent Grainger on Wicked City, played a crime lord on Snatch, and sold double-glazed windows on White Gold. Is there any role he can't play? Most recently, Westwick stars in the movie DarkGame.

With a background in music, Westwick also currently sings in the bandFor You. Their most recent release is the song "Tailspin," and they're set to release a new single "Here Comes Trouble" in March 2024.

Westwick had been dating model and actress Amy Jacksonsince 2021, with the pair getting happily engaged during a ski trip in January 2024.

Chace Crawford (Nate Archibald)

Following his stint as a wealthy Upper East Sider on Gossip Girl, Texas native Chace Crawford tried his hand at playing a greedy oil worker on ABC's short-lived TV series, Blood & Oil. He's had several film roles since – you can catch him in movies like Undrafted, Eloise, Nighthawks, even voice-actingin Belle. Most recently, Crawford stars as The Deep on The Boys.

Crawford has previously dated Carrie Underwood, Rachelle Goulding, and Rebecca Rittenhouse, though he is currently single as a Pringle.

Jessica Szohr (Vanessa Abrams)

Jessica Szohr, who played Dan Humphrey's BFF slash on-again, off-again girlfriend (needless to say, we were confused too), has been a lot busier than her character was after season four, when she was all but written off the show.

In the years since Gossip Girl, the actress scored several roles on TV shows such as Complications, Kingdom, Twin Peaks and The Orville. She even starred in Taylor Swift's music video for "22" back in 2013!

Jessica also welcomed a daughter with her longtime boyfriend in early 2021.

Jessica currently hosts a podcast called "XOXO" that dives deep into the Gossip Girl cast, crew, and behind-the-scenes moments. Some notable episodes have featured Zuzanna Szadkowski (Dorota), Aaron Tveit (Tripp van der Bilt), Kelly Rutherford (Lily van der Woodsen), and Michelle Trachtenburg (Georgina Sparks).

Michelle Trachtenberg (Georgina Sparks)

Since her stint as the "bad girl" Georgina Sparks, Michelle Trachtenberg has landed roles on shows like Criminal Minds, NCIS: Los Angeles, Sleepy Hollow, and Sister Cities among other numerous series and movies. She even reprised her role as Georgina for the 2021 remake of Gossip Girl on HBO Max!

She's managed to keep her personal life largely out of the tabloids, including her dating life. The last update on her relationship status was in 2023, and that she was dating her talent agent, Jay Cohen. She reportedly previously dated Shawn Ashmore, Joshua Radin, and Jason Segel.

Kelly Rutherford (Lily van der Woodsen)

Besides being a New York Fashion Week icon (we'd expect nothing less of Lily van der Woodsen's alter ego!), Kelly Rutherford has popped up in several TV shows over the years, including Quantico, Jane the Virgin, and Dynasty.

She also frequently travels to France and Monaco, where, after years of custody battles with her second ex-husband, Daniel Giersch, she has extensive visitation rights to see her two children, who reside there with their father.

"Yes, it was a challenging time. It was a heartbreaking time," she told People. "But I focus on the good most of the time, I really do," she says. "I'm very thankful of where we are. I have a great relationship with my kids."

When she's not with her kids or working on a project, Kelly is dropping iconic 'fit pics on her Instagram account.

Matthew Settle (Rufus Humphrey)

Matthew Settle, who played rockstar dad Rufus Humphrey, continued acting after the Gossip Girl cast dissolved. He hasn't been on any other TV shows other than one episode of Criminal Minds: Beyond Borders in 2016. He mostly stuck to movies, acting in titles like Ouija, Marshall the Miracle Dog, and Valentine: The Dark Avenger.

Settle is also a dad of two children, having welcomed his first with actress and model Naama Nativ in 2009. He had divorced her in 2011 and went on to have a second baby with girlfriend Maria Alfonsin in 2015.

Zuzanna Szadkowski (Dorota Kishlovsky)

Though Blair's loyal maid and, ultimately, best friend, wasn't technically a main character, there's no denying that it would have been a different show without her unwavering presence! Zuzanna Szadowski has dabbled in film and television since then, appearing in shows such as Girls,The Good Wife, and Modern Love.

In 2010, she partnered with Sam Weisman to open The Sam Weisman Studio, an acting school (now closed).

Oh, and did we mention she just so happens to be one of Leighton Meester's real-life BFFs?

Ferrell’s Buddy the Elf meets Zooey Deschanel's Jovie at a department store when he treks to New York City to find his long-lost father. Though she appears jaded at first, she eventually gives in to the holiday spirit, and even helps save Christmas by singing in public to lift Santa’s sleigh.

Deschanel was great in the role, but according to Variety, she wasn’t actually the first choice. “I went in as a backup. The person they cast couldn’t do it,” Zooey explains. “A lot of the parts I got early in my career, I was filling in for someone else who had dropped out last minute.”

This is definitely crazy because Zooey Deschanel *is* Jovie in our eyes and we literally cannot imagine anyone else playing the role.

Prior to Elf, Deschanel appeared in 2000’s Almost Famous and 2003’s All the Real Girls, and she had been auditioning for another movie when she was asked to come in for Jovie. That other movie, in fact, is the reason for her blonde hair. “What is funny is I had dyed my hair for a screen test for a movie that never happened,” she continues. “I had a meeting for Elf while I was blonde, and I asked them if I could dye my hair back brown. They said, ‘No, we want you to look the way you did in your audition.'”

We have to wonder if she would have gotten the role if she had shown up with brown hair, but we’re glad things worked out the way they did!

Beach Houses

East Hampton Beach Cottage

Cost: $44,500,000

The Hamptons are known for their clean, chic shingle architectural style, and this "cottage" is no exception to that. And while I absolutely adore the inside of this home, it's the grounds that really get me at the end of the day. Think about all the beautiful backyard dinner parties you could throw!

Destin Beach House Destination

Cost: $4,100,000​

Who needs a time share in Destin when you could own all this?! This airy, beautiful house takes coastal home style to the next level. I love the sandy, earthy tones paired with the light blues and open space. And for less than 10% of the Bridgehampton beauty above, this is basically a steal, right? 😉​

Marvelous Marco Island Getaway

Cost: $5,450,000

I vacation on Marco every year with my in-laws, but I can PROMISE you our one-bedroom timeshare (that I love) isn't anywhere near this stunning super home. Swipe through photos to see how gorgeously staged this multi-million dollar home is — I promise it won't disappoint!

Laguna Beach Beauty

Cost: $21,500,000

Obviously Laguna Beach is known for so much more than the hit MTV show, but I can't untangle the two. So in my mind, this is the home Lauren Conrad's parents worked on in Season 1 Episode 1 — a $20+ million dollar stunner that I would later stare at on Zillow. It's not true, but wouldn't it be fun?

California Dream House

Cost: $55,000,000

Not only is this a dream house because of how it looks, but also because I could only afford this in my literal wildest dreams. Unless someone decides to discover me on the New York streets for the funny, talented gal my parents think I am, this is strictly a mood board manifestation moment. (But, what if?!)

At Home In The Hamptons

Cost: $79,995,000

Oh, how I could wax poetic about this $80 million Bridgehampton beauty. Shall I compare thee to a summer's day? Ya know...the one I would love to have in this very house? Just lounging, living luxuriously? That imaginary inheritance I daydream about could reaaaaaally come in handy right about now.

Fantastic Florida Beach Cottage

Cost: $9,950,000

In case you can't tell, none of these homes are "cottages" outside of their aesthetic. While this six bedroom, four bathroom may look humbler than the rest, the cost should indicate what we're working with here. Each room is so perfectly curated, and to have all this right in the heart of Naples is absolutely everything. I could see myself sitting by that fire for SURE.

Condos & Townhouses

Gorgeous Georgetown Condo

Cost: $5,495,000

DC is more than just Capitol Hill, and this Georgetown Condo proves it! The natural light, the natural wood accents, and the big, airy rooms make this home a welcomed reprieve in on of the busier U.S. cities. And while you're getting a lot in a small package (three bedrooms for $5+ million...😭), you're really paying for the neighborhood. Georgetown really is full of beautiful townhouses, great restaurants and bars, and overall good vibes.

Upper East Side Excellence

Cost: $65,000,000

Hello, Upper East Siders...Zillow Girl here! All jokes aside, this $65 million townhouse is giving all the old money luxe that Chuck Bass and Blair Waldorf would settle into quite nicely. The molding, the wraparound staircases, and the sheer size alone are something else, but the biggest surprise here? TEN BATHROOMS. TEN!!!!!!

Totally Airy Brooklyn Townhouse

Cost: $6,950,000

Good new, girls! This totally killer townhouse had a $300,000 price cut last month, bringing it to...just under $7 million! While I try to fix my eye twitch after writing that, scroll through to see the gorgeousness that is this literal mid-century modern four-story home. It's like a little (big) oasis in the middle of the big city!

Beautiful Turn-Of-The-Century Brooklyn Townhouse

Cost: $6,995,000

I've said it once and I'll say it again: Carroll Gardens in my dream neighborhood. It's got all the Brooklyn charm with its brilliant brownstones, lively dining scene, and tree-lined streets. Plus, it's so incredibly close to Prospect Park for all your summer strolls with the kids or the dogs or yourself or whomever! And while I could go on and on about the location, the townhouse itself is kitschy with it's mix of classic and modern details.

Mountain And Lake Houses

Charming Wyoming Ranch House

Cost: $8,199,000

It feels a little silly to call a nearly $10 million home "charming," but here we are. This modern ranch-style mountain house looks unassuming from the outside. And the four-bedroom inside is really nice, too, don't get me wrong. But what really makes this worth it, if I had to guess? The freaking VIEW. Can you imagine sipping your coffee and staring off into that horizon every morning? Yes, please. I would like one of these.

Cozy North Carolina Castle

​Cost: $7,500,000

Ah yes, nothing cozier than a literal castle-sized house in Appalachia. In all seriousness, the dark wood accents give you that almost cabin-esque feel that the mountain range so obviously calls for. With 10 bedrooms, this is the perfect retreat for your family get-togethers! You can enjoy each other's company across the estate, or you could...find a little hiding spot and nobody would know the wiser. 😉​

Sante Fe Getaway

Cost: $3,375,000

The most affordable of the bunch, this single-story Sante Fe residence is a dream-come-true! You've got lake views, trails, and even a golf course if that's your thing! My personal favorite part of this lovely little home, however, is the wine cellar. Can you imagine being like, "Yeah, just go grab a bottle from the wine cellar"?! Like I said, dream-come-freaking-true!

Lovely Michigan Lake House

Cost: $3,649,000

The windows alone are enough to make this house the dreamiest escape, let alone the private and super exclusive access to Lake Michigan. This home may only have three bedrooms and four bathrooms, but each room feels intentional, spacious, and utterly luxurious. I'd definitely dip my toes in that water!