Whether you’re celebrating Valentine’s Day with your significant other, your friends or solo, building a stylish outfit to wear is always a must for the occasion. And what better source of inspiration than the New York City classic TV show “Gossip Girl” and its iconic cast of characters? In anticipation for this Valentine’s Day, channel the polished, preppy style of the Upper East Side with these curated Gossip Girl character outfits.
![](https://nyunews.com/wp-content/uploads/2025/02/vday-gossipgirl-blair-1-600x400.png)
Blair Waldorf
We’re starting off strong with the Queen B herself: Blair Waldorf. With a Chanel bag, kitten heels and a houndstooth tweed set — all in a light bubblegum pink, of course — this outfit inspired by Waldorf lives up to her preppy, chic personality and style. Waldorf’s fashion, which features many quintessential Upper East Side outfits, emphasizes combining timeless pieces with a statement touch. Tweed, which first entered the fashion spotlight in the early 19th century, remains in style today. And since the ’20s, quaint Mary Jane shoes have continued to appear in everything from designer collections to school uniforms. Even if you don’t have a Chanel bag casually sitting in your closet like Waldorf, you can still opt for a pink monochromatic color palette to add the essence of Valentine’s Day to this otherwise classic outfit.
![](https://nyunews.com/wp-content/uploads/2025/02/serena-600x400.png)
Serena van der Woodsen
The ultimate carefree, glamorous it girl, Serena van der Woodsen’s natural poise is reflected in her effortless style. She’s often spotted in a brown suede or leather jacket, which is best paired with a black bodycon dress, black slingback heels and a cheetah bag. These pieces remain staples in New York City fashion. Without even trying, van der Woodsen is always the star of the show, and channeling her polished yet spunky style will give you the confidence to nail any Valentine’s Day date.
![](https://nyunews.com/wp-content/uploads/2025/02/vday-gossipgirl-jenny-1-600x400.png)
Jenny Humphrey
In the first season of “Gossip Girl,” Jenny Humphrey’s style is cheerful and full of color. However, as the aspiring fashion designer and Brooklyn native begins to grow out of her shell as one of the show’s younger characters, her style begins to incorporate more edgy pieces. Jenny’s Valentine’s Day look embodies this transformation, combining a bold heart-shaped purse and tall black boots with a black pleated skirt, collared white shirt and leather jacket. Use this outfit as inspiration if you’re looking for an edgier Valentine’s look.
![](https://nyunews.com/wp-content/uploads/2025/02/vday-gossipgirl-dan-1-600x400.png)
Dan Humphrey
Simple, laid-back style is a must for Dan Humphrey, who is always spotted with his signature messenger bag and cup of coffee. Like Humphrey himself, this look isn’t afraid to challenge norms. While most “Gossip Girl” characters might wear designer brands for even the simplest outfits, Humphrey would probably reject the idea of splurging on a fancy outfit just for one day of the year. There’s no shame in using the tried-and-true sneakers, jeans and a sweater formula to create an easy, yet put-together look. Try adding a white collared shirt beneath your sweater for a bit of preppy Upper East Side flair.
![](https://nyunews.com/wp-content/uploads/2025/02/nate-600x400.png)
Nate Archibald
To capture the charm of Nate Archibald, whose effortless sophistication channels a nautical style, pair light-colored jeans and brown loafers with a bright poplin shirt. This outfit works for both formal dates and group get-togethers for Valentine’s Day. To combat the cold weather, throw on a wool dress coat or trench coat on top.
Contact Jada Lee at [email protected].