Best Fashion on Gossip Girl: Menswear

It’s official! The Gossip Girl reboot is happening.

The prestige series will address just how much social media—and the landscape of New York itself—has changed,” stated the press release obtained by Vulture. “

As we wait for the all-new show that will air in the spring of 2020 on HBO Max, let’s look back on the best menswear fashion seen on male leads Dan Humphrey, Chuck Bass, and Nate Archibald. Which one are you?


Played by our former cover star Penn Badgley, Dan Humphrey is one of the main characters of the show. Dan aka Lonely Boy doesn’t come from a wealthy family. He had worked for everything in his life and these experiences shaped his admirable character: hardworking, smart, and level-headed.

Dan’s style is casual chic. A healthy obsession with V neck t-shirts (perhaps to show off that great chest hair) and a blazer, Dan likes to keep it functional but stylish. Think Silicon Valley, startup/creative person kind of guy.

Is he sloppy dresser? Maybe. Does he care? No. He is confident like that.

WATCH: Behind The Scenes Video of DAMAN December 2018/January 2019 Cover Star Penn Badgley


Chuck Bass, brilliantly portrayed by Ed Westwick, is a filthy rich playboy in the Upper East Side. He is the billionaire bad boy everyone loves-hates. His life changed when he met Blair Waldorf.

A purveyor of bow ties, suspenders, and tuxedo suits for daily wear, Chuck is vain. He loves fashion just as he loves girls. An icon of dandy style, Chuck is always impeccably dressed. We are certain his luxury suits are all custom-made; he probably sends master tailors to New York for fittings.


Nate Archibald is Chuck Bass’s best friend. Played by Chace Crawford, Nate Archibald is the golden boy of the Upper East Side. A heartthrob, he went to have a number of romantic relationships but none proved successful.

Perhaps it’s the influence of his business tycoon daddy or maybe his aspirations in politics, but Nate’s style is very corporate chic. Nate loves neckties. Neckties and a good amount of hair wax.

Nate Archibald’s very Wall Street-ish style is a great inspo for budding professionals who want to know how to match a crisp shirt with a plain or patterned/printed necktie.

Which Gossip Girl man is your style? Leave a comment.