When it comes to the best dressed fictional characters, Serena Van Der Woodsen from “Gossip Girl” is definitely at the top of the list. Van Der Woodsen is portrayed by the equally (if more) stylish Blake Lively and she did a great job bringing the character to life. To be quite honest, everyone on this show dressed impeccably but I gravitated towards Serena’s style more than the others. I wanted to go through all of her outfits and find the twenty best ones through the show’s six-year run. So in no particular order, here are her best outfits. SPOILER WARNING AHEAD!!!
1/20
First, I have to start with her iconic pilot fit. She is wearing a button-down brown leather jacket, a black and white striped shirt, dark wash jeans, a chunky belt, a yellow ascot, and Louis Vuitton luggage.
2/20
I am so incredibly obsessed with these wide-leg pink pants. I have tried to find the perfect replicas forever and I just can’t succeed. Serena wore this outfit on a trip to Paris with Blair where the two friends decided to go shopping. She paired the pants with a tan-colored tank top, chunky teal jewelry, an oversized bag, and a hat.
3/20
Serena wore this gorgeous shimmery orange gown to a polo event. The dress is one-shouldered and has an intricately braided belt. I love the slight shimmer that the dress has and the color is really unique.
4/20
Next, I have this red-orange dress that she and Blair stole from Blair’s mother’s store. Blair wore the matching blue one and the dresses are so fun and compliment each other so well.
5/20
This short, burgundy, bodycon dress is one of the lesser glamorous dresses on this list, but it still is so pretty. I think the cutouts on the top are very unique. She paired the dress with gold strappy heels and a gray clutch.
6/20
This outfit is one of my favorites and I was shocked to hear that many people actually hate it. She wears this beautiful gold bomber jacket with accentuated shoulder pads. She pairs it with a simple white tank top and electric blue, cropped pants and wore studded brown heels with a gray crossbody bag.
7/20
I can’t make a list of her best outfits and not include the cotillion dress that she wore in season 1. It is a ruched gold gown that is almost kind of ugly, but somehow she makes it work. The top has glittery gold detailing which adds a bit of pizazz to the gown. No matter what you think of the gown, she wears it in one of the most iconic episodes of the entire show, so you have to have at least some appreciation for it.
8/20
I am so incredibly obsessed with this Georges Chakra pink mini dress that she wore in the Paris episode. I searched and searched and searched all over the internet in hopes to find one, but was unsuccessful. The dress is blush pink chiffon, with a glittery rose gold cage detailing all over the front. She pairs it with a gray blazer, hat, and printed crossbody for a perfect Parisian look.
9/20
This was one of Serena’s more toned-down looks, but it is still effortlessly chic. The purple striped blazer is so sophisticated and she pairs it with a white blouse, dark jeans, knee-high brown boots, and a crocodile purse..
10/20
What an iconic look from one of the most iconic episodes. Serena’s white party dress that she wore in the Hamptons is incredibly elegant and beautiful. Her hair is done up in a messy but gorgeous updo with long beaded headbands and accessories to match.
11/20
Jenny Packham is one of my favorite designers and this dress is definitely one of her most unique. This entire look is not something that I think you would typically see Serena in but she totally pulls it off. I love how the black and white pattern is contrasted with the bright blue on the collar and belt.
12/20
This sparkly, strapless, black dress is one of Serena’s most elegant looks. It is not too over the top and not too understated which is why I love it.
13/20
Talk about an iconic outfit in yet another iconic episode. I’m talking about the infamous Thanksgiving episode where revelations are thrown left and right as the food is being served to Jason Derulo’s “Whatcha Say.” At first glance, the outfit appears to be a dress, but it is actually a jumpsuit!! The mesh on the bodice is so intricate and the entire look is so fun for a less than fun episode.
14/20
This is another Jenny Packham gown that I am so incredibly obsessed with. The beading on the shoulder is so intricately and beautifully done and the brightness of the coral really compliments Serena’s complexion.
15/20
Serena really nails this 1920s inspired look for Chuck’s Halloween party. The beading on this gown is so complex and the dress looks like a piece of art. I love the mini cape that she wears with it and the sparkly fishnet tights.
16/20
One of her simpler dresses is this bright blue one that she wore while walking the streets of New York. I love the brightness of the dress and the contrast of her pink heels. She paired the dress with dangly earrings and a patterned purse.
17/20
Serena wears this bridesmaids dress to her mother’s wedding to Bart Bass, Chuck’s father. The dress is equal parts beautiful and ugly. The pattern is a lot to take in and the insane amount of ruffles really make this dress. The jarring black belt and flower on the collar tie the dress together.
18/20
This is my all-time favorite look from Serena. This gray beaded, lace, and chiffon gown is so gorgeous and Serena really pulls it off. She holds a small black clutch and pairs the dress with gray drop earrings. The draping of the gray fabric on the bodice is so fun and this whole look screams class and elegance.
19/20
I so wish we could have seen more of this gorgeous gold gown that Serena wore in the 1970s themed episode. This gown has a cowl neck and is floor-length. She wears a chunky gold necklace to match the gown and a ton of gold bangles. Her hair is perfectly teased and curled in such a disco fashion and she really plays the part perfectly.
20/20
To end my list, I have to include her incredibly unique wedding gown that she wears to marry Dan Humphrey. The dress is GOLD which really is Serena’s color. It is very unorthodox for a wedding gown but is perfect for her. The white chiffon skirt is absolutely gorgeous and the entire look is a work of art. It was designed by Georges Chakra. She wore dramatic earrings and had her hair up in an elegant updo. The look may not be my favorite for a wedding dress, but it is perfect for Serena.
Serena Van Der Woodsen is one of the best dressed fictional characters of all time. She may not have been the best character with the best personality, but she sure did know how to dress. Blake Lively did an incredible job bringing her to life and I could not think of a more fashionable person to portray her.