Y2K is making a comeback thanks to Gen Zers who are, for some reason, nostalgic about the era of non-existent eyebrows and low rise jeans that did not look flattering on anyone who wasn’t a size 0. Unpleasant memories of the 2000s aside, even I have to begrudgingly admit that there were some really solid fashion trends to come out of that period. To be specific, I’m talking about the 2000s preppy trend, the granddaddy of the 2010s Dark Academia fashion style.
But the resurgence of Y2K has left many fashion icons forgotten. Sure, you get the odd photo of Brenda Song or Paris Hilton in some teen fashion lover’s Pinterest mood board, but fashionistas who remember those years know in their hearts there’s something, someone missing.
This entire time we’ve been bringing back Y2K and we’ve forgotten about the Miss Blair Cornelia Waldorf from the CW Network’s hit series Gossip Girl.
The Fundamentals of a Blair Waldorf Outfit
Blair Waldorf doesn’t need an introduction so let’s jump straight into it. No matter what Blair is wearing, whether it be a patterned dress or a sensible suit, her outfits always have her signature style written all over them. This visual cohesion makes it easy to recognize that an outfit is supposed to be hers. This uniqueness becomes clearer when you look at her clothes side by side with the kind Serena van der Woodsen or Jenny Humphrey wear.
While all three Gossip Girl leads can look very polished, there’s a grungy feel to Jenny’s looks that are easy to miss if you don’t look for them (i.e.- a dark lipstick or a lack of non-black touches on her ultra prep Constance Billard uniform).
On the other hand, you have Serena whose fashion choices always have a carefree boho feel to them. It’s easiest to spot in the scenes where she wears actual boho dresses, but she also prefers long, swaying necklaces and always keeps her hair in a constant state of “I don’t know, the wind just blew on my way here and left my locks like this.”
Not Blair Waldorf.
One of the main things that set her outfits apart is the fact that she never wears jeans. At least, as far as I’m aware. My younger brother is a big Gossip Girl fan and has watched the show in our living room enough times that I’ve seen every single one of Blair’s outfits ad nauseum.
Here’s the thing: she rarely wears jeans. I want to say “never” but I vaguely remember an episode where she wears jeans with a loose top. I don’t think she’s ever worn shorts in the show. It’s always dresses and skirts with her.
On that note, Blair’s hemlines often end roughly a handspan over her knees. Short enough to be cute or suggestive, but never “too short.” Her dresses and skirts often have an A-line cut with some notable exceptions, one of which you’ll see later.
Since Blair is often seen with Serena, it’s impossible to notice that she isn’t exactly as drop-dead sexy as her best friend. This isn’t to say Blair isn’t hot, I mean, come on, it’s Leighton Meester, but she isn’t Serena. Blair’s outfits seem to take this into account.
We often see her wearing stockings in the show, usually solid-colored with maybe a lace or crochet design every now and then. The smart use of stockings instead of Serena’s long socks complements Blair’s figure.
Speaking of figure-suiting clothes, Blair Waldorf’s clothes always fit her perfectly. You never see her in the oversized top and shorts combos that Taylor Momsen’s Jenny rocks or in the daringly small and tight clothes that Serena sometimes wears. Blair’s outfits always look like they’ve been made to her exact measurements, giving everything she wears a clean and polished look.
Of course, we can’t forget the headbands. While Blair wears a number of accessories throughout the show, she never commits the Y2K sin of being overaccessorized to the point that she looks like a Christmas tree. Most of her looks are topped off (literally) with a tasteful headband that no one would bat an eye at even in 2022.
8 of Blair Waldorf’s Best Looks Throughout Gossip Girl
1. Her Ultra Preppy Constance Billard Uniform
This classic Blair Waldorf outfit is just one of the Gossip Girl character’s many riffs on the Constance Billard uniform. Well, “uniform” is a bit of an overstatement since every character in the show seemed to have their own version of it. Still, they’re always recognizable as uniforms which makes the customized versions the characters have of it a great way to communicate their personality.
In Blair’s case, she’s always giving us posh girl.
While none of the other female characters are fashion slobs, Ms. Waldorf is easily the most dressed up out of all of them. Her coats frame her shoulders in a way that adds to her air of confidence and it helps direct your attention to her face.
Aside from the headband, viewers will notice that Blair’s hairstyles tend to vary a lot, but she never uses the same messy look that Jenny does. Her signature hairdo, the one where she wears her brown hair in big, shiny curls, makes her look like she got up at 5:00 in the morning to do it and she’s proud of that.
2. The One Where She Makes Uggs Look Good
It doesn’t matter what time of the year it is. You are never catching Blair in a bad outfit, even if she’s wearing uggs.
Uggs may have been memed to hell and back now for its ties to what is colloquially called “basic b-word” culture, but Blair manages to make it look like the kind of footwear a woman of class and taste would wear.
In the photo above, you can see that she’s worn it with a pair of white stockings, a clothing item that appears in a handful of her other looks throughout the show. It looks like she’s wearing a navy blue skirt (or dress) over the white stockings. Maybe it’s the navy blue sailor dress we see her wear in episode 18 of season 1.
3. This Gray and Mustard Moment
Did she just walk off a runway or did she just walk off a runway? I don’t want to say Blair was the only person in the show who always looked like she just got out of a photo sesh with Vogue because Chuck Bass does look like that too most of the time. But Vogue is a women’s fashion magazine so maybe it wouldn’t be an injustice to him.
Leighton Meester is wearing a grayish-green ensemble with a surprisingly subdued pop of mustard yellow in this one. As usual, Blair wears a pair of tights, a gold and black printed skirt, and a mustard blouse.
From the little we can see, it looks like the blouse has bishop sleeves and a bow. Something like this blouse, perhaps? And while I can’t figure out which exact bag she’s carrying on her arm, you could probably recreate the look with this Hermes Birkin. Or, if you’re a peasant like me, this lookalike from Kate Spade.
4. Only Blair Waldorf Could Make Victorian Swimsuit Look Sexy
Only Blair Waldorf could pull off a 50s pinup and Victorian schoolboy swimsuit crossover.
Our sassy Upper Eastside queen sports a pair of polka-dotted gloves and a bright red bucket bag. Though conventional fashion wisdom these days tells you not to wear more than three colors at once, Blair manages to make four work. That said, that might have something to do with white being a neutral color and the fact that the red bag and green scarf thingy she wears are both lean towards blue.
5. Blair’s Princess Dress
Let us all take a moment to say chef’s kiss.
Blair wore this pink cupcake and cream fur collar cardigan combo in episode 19 of season 5, where Chuck helps her get out of a sticky legal situation with the Grimaldis. Though Blair always adds a decidedly girly touch to all of her looks, this outfit is just a full-blown girly girl princess fantasy dress that would make Legally Blonde’s Elle Woods proud.
The entire look screams expensive, but don’t let the crown fool you. It’s not the most expensive thing Blair is wearing. That honor goes to the bubblegum pink Oscar de la Renta gown she’s in.
6. Chuck Bass and Blair Waldorf Reminds Us That They Are THE Toxic Power Couple
Business casual? More like business haute couture.
Chuck Bass and Blair Waldorf are the premier toxic duo of Gossip Girl and their personal styles make sure we mentally lump them together. The two are often seen in old money-esque outfits that make them look like they’re off to the races with the British royal family. Sure, they may not be paragons of emotional health, even when they’re together, but damn if they don’t look good standing side by side.
In this photo, Blair wears a sensible charcoal gray pantsuit with dark red lipstick and nails. The noticeable lack of head accessories makes it appear more mature and takes away Blair’s girlish charm. This is business Blair and business Blair is not here to chat about taffeta over tea and macarons. Still, the printed navy blue silk blouse is a subtle and subdued version of the next outfit on this list.
7. This Very 2000s Floral Dress That’s Giving Doja Cat Vibes
Look, there are only three other people I can visualize this dress on and that’s Doja Cat, Elle Woods, and Paris Hilton.
Blair Waldorf is wearing what looks to be a silk and/or chiffon dress with pink and green floral print. This dress is one of Blair’s shorter ones with its hemline ending somewhere in the upper part of her thighs. The hemline also ends in a bubble, giving the dress, which would otherwise look like a shift dress, a bit more structure to fluff the skirt out a bit.
The top half of the dress is where it gets more interesting. I had to look twice because for some reason my brain thinks it’s a scarf tied into a rose-like shape. It is not. That is the actual fabric of the dress pleated to make a flower that matches the one shown on its print. All these little details make it a bright, feminine spring outfit that’s somehow eye-catching yet understated at the same time.
It’s a perfect look for a Y2K wedding guest which is exactly what Blair was in episode 18 of season 1 where she wore it to Lily and Bart’s wedding. Incidentally, the title of the episode is “Much ‘I Do’ About Nothing”, making the midsummer vibes on this outfit spot on.
8. This Lemony Yellow Summer Fit
Outfit #3 on this list was a subdued yellow-accented look fit for fall. This summer outfit, though? It’s taking out the big guns with a lemon yellow and bright orange ensemble that makes Leighton Meester glow in the late afternoon sun.
It takes a lot of fashion know-how to pull off an outfit this loud and bright as the yellow and orange pairing could have easily ended up looking tacky. Instead, Blair manages to make it work by sticking to a classic silhouette and equally classic accessories. The simple orange bag and pumps aren’t visually overwhelming, allowing the eyes to focus instead on the lovely lemon and floral print on Blair Waldorf’s skirt and the ruffles on her solid yellow blouse.