How The ‘Gossip Girl’ Cast Looked On The Show Vs. How They Look Now

Now, like Serena was on the Upper East Side, Lively is a veritable style icon, serving glamorous high fashion look after look. I guess sometimes life does really imitate art. Oh, and the star of The Shallows is also married to husband Ryan Reynolds and has two adorable children.

Taylor Momsen played Dan Humphrey's baby sister, Jenny, a wide eyed innocent who soon finds herself caught up in the rebellious and dangerous world of the rich and famous. If that sassy look and plaid uniform don't scream "I'm a good teenager about to rebel", then I don't know what does.

Momsen has ditched the fresh-faced look in favor of some heavy black liner and a mic. She's currently the lead singer of the rock band The Pretty Reckless — a far cry from the posh brunches of the Upper East Side.

Ed Westwick played Chuck Bass, fans' favorite playboy. Though he often did some reprehensible things, Chuck's soft side, and his love of bad scarves, captured the hearts of everyone who watched.

Westwick also clearly enjoys taking some fashion risks in real life, and has maintained his character's enthusiasm for plaid. With an improved haircut and a little scruff, Chuck is all grown up.

Playing Dan's old friend Vanessa, Szohr rocked many colorful outfits, including this T-shirt and bomber jacket combo. I think the wardrobe was supposed to demonstrate that Vanessa was from a different world than the Upper East Siders, but TBH I always thought she looked cooler than Blair.

Now, this sleek beauty looks great after ditching the bright yellow tees in favor of an LBD, and opting for some trendy ombre treatment in her hair. No need to pine after Lonely Boy anymore, Vanessa.

Szadkowski played Blair's darling maid, Dorota. We didn't get a chance to really see her style shine, since she was mostly wearing that heinous uniform.

Work it, Dorota! At this event, Szadkowski ditched the frumpy uniform for a super cute embroidered dress and some oversized hoops. Dorota is giving Blair a run for her money.

Chace Crawford played Nate Archibald, the nice guy to Chuck's rebel, and sported some seriously beautiful gelled locks.

Now, Crawford has the same steely blue stare, but has gone from a boyish clean shave to a good deal of scruff. The actor was most recently in the since cancelled series Blood & Oil, but hopefully we'll be seeing more of him soon.

Rufus Humphrey was a "cool dad." With that leather necklace, mismatched outfit, and shaggy hair, Matthew Settle looked like he was ready to front Death Cab For Cutie.

...Rufus? Is that you? Honestly, Settle still looks young. The haircut has done wonders, even if it's a little less rock n' roll.

Connor Paolo played Eric van der Woodsen, Serena's little brother who struggled with mental health issues throughout the series. He certainly looks the part of a teenage boy with that mop of blonde hair.

Paolo is certainly looking more grown up these days, but I can't say that I'm a big fan of that hat. After Gossip Girl, Paolo had a role on the ABC drama, Revenge.

Scheming "cousin" Ivy Dickens (alias Charlie Rhodes) was hired by Serena's aunt Carol Rhodes to pretend to be her daughter in order to gain access to her trust fund. Even though the girl was a snake, she was also sympathetic due to her turbulent past, and her relatable awe with the glamorous life of the rich and famous. Judging by the outfit above, it clearly didn't take her long to dive headfirst into the glam lifestyle.

IRL, DeFer looks like she is living the glam life herself. Even that blonde woman in the background can't take her eyes off the actor and her sparkly belt.

Kelly Rutherford played Serena's elegant mom, Lily van der Woodsen. Sure, she looks all high society with her expensive jewelry, but we soon find out that she used to date Rufus. Gasp!

Pretty in pink. Rutherford still looks every bit the Upper East Side glam mom, even if she's taking a few more fashion risks in real life than the buttoned-up Lily did in the show.

Georgina Sparks was the rebellious troublemaker who returned to stir up drama for Serena. Can't you tell by her leather jacket and evil glance?

Trachtenberg still looks a little bit like she could be hiding something, but she's broken up the moody black with some bright pink flowers. Maybe Georgina has turned a new leaf?

Setton played backstabbing clique member Penelope Shafai, who alternated between serving Queen Bee Blair and Queen Bee Jenny. She was particularly distinctive for her ultra-preppy looks. I mean, just look at that thick white headband.

In real life, Setton looks like she prefers a casually cool look. She's recently appeared in other popular TV shows, such as The Mindy Project and Hawaii Five-O.

For a while there, Blair really was being treated like royalty. She first met her one-time husband Prince Louis of Monaco in Paris, and he swept Blair (and the rest of America) off her feet. He might have been a smooth talker, but in the end he turned out to be kind of a jerk... a very, very handsome jerk.

Becker is just as dashing as the prince in real life, even if he's a little less clean cut. In addition to his run on Gossip Girl, Becker has also appeared in movies and television in Britain and France.

Chang played Nelly Yuki, a nerd who was sabotaged by Blair at the SATs, but later joins her clique only to then give Blair's new fashion line a terrible review during Season 6. I think those glasses were supposed to make Nelly look like a dork, but they look pretty hipster to me.

No nerds here. With lightened hair and without the specs, Chang almost looks like a different person entirely. Blair who?

Ah, yes, Blair Waldorf. The girl we loved to hate and hated to love, infamous for her scheming ways and thick headbands (a particularly bright one pictured here). Whether you wanted to be her best friend or wished that she would get the comeuppance she often deserved, you can't deny that a tiny part of you always wanted to be Blair.

In real life, Meester shares Blair's love of taking fashion risks, but not her affinity for headbands. She's done everything from starring on Broadway to topping the pop charts ("I make them good girls go bad"), and she now has a daughter with husband Adam Brody.

Lonely Boy. Dan Humphrey. Gossip Girl. Honestly I have a hard time keeping up with Dan's plot lines, and the reveal that he was Gossip Girl all along inspired the hatred of many diehard fans. But he did it for love — and to make himself relevant in the lives of the rich Upper East Siders.

In real life, Lonely Boy has been growing out his hair, his beard, and, it seems, his chest hair. Also, Badgley totally agrees with you that there is no way Dan could have been Gossip Girl. It's just, like, impossible. Badgley is currently the lead singer of the band MOTHXR, and doesn't have time to keep up with the lives of Manhattan's elite anymore. Guess it's up to me now... XOXO.