Meet The Fashion Favorite Breaking Down Blair Waldorf’s Best Looks

To live in New York is to frequently reference two television shows. Any sexcapade quickly leads to the self-identification of one of four characters (I’m sure I don’t have to name them), but for all the rest of your experiences and preferences—personal style, taste in men, work ethic—only two women matter: Blair and Serena.


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To know New York fashion is to love Tyler McCall. The editor (formerly of Teen Vogue and WWD, currently residing at Fashionista), has become one of the industry’s most beloved mainstays…she’s also, for the record, a Blair. While for many of us being Blair Waldorf or Serena van der Woodsen is innate, often undiscussed but starkly obvious, McCall wears her Blair-dedication daily. The editor stops short of cosplay, instead updating Blair’s trademark Upper East Side prep with the Instagram gen’s embrace of high-low (with more head accessories).


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I prefer @chanelofficial snow to just about any other. ❄️⛄️📷: @katcollings

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Speaking of the social platform, McCall has dutifully utilized hers to take her love for Blair Waldorf one step further: breaking down actress Leighton Meester’s costumes over Gossip Girl‘s five-year run. Frankly, it’s a public service. We caught up with McCall to discuss headbands, the best of Blair’s bold femininity, and why Gossip Girl‘ still hits—even seven years 0n.


‘Are you a Blair or a Serena?’ is a question much of our generation can relate to. What is it about Blair that you connect with?

First of all, I’m very a Type A, controlling, bossy person. I could not relate to Serena’s freewheeling spirit (or her unbrushed hair—girl, you can afford a Mason Pearson!). Blair was a character who valued control over everything else, oftentimes to a fault. And, on a purely surface level, I also felt like she had the far superior wardrobe.


Why do you think Gossip Girl’s popularity is so enduring?

It was just such a perfect time capsule of that era. At least, that’s why I think it’s remained so popular with people who watched it while it was on air. I think Netflix has also given it a whole new life with people who weren’t quite of age when it was first on television. It’s also just eye candy! Between a good-looking cast, beautiful sets, and killer costumes, there’s very little to find fault in—at least, until it gets to the plot lines of later seasons.


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Hello Upper East Siders, and welcome to another #WaldorfWednesday! There’s Royal Baby buzz in the air, so let’s talk about a royal baby of a different sort: Blair Waldorf’s brief pregnancy arc. I know we all want to forget about the storyline as quickly as Blair apparently forgot she lost a baby after a paparazzi-caused car-crash (what WAS that?!) but it happened and we just have to deal with that. —– This may be our first season 5 outfit, because I hate literally everything about season 5! But in episode 8, “All the Pretty Sources,” Blair goes for maternity chic in this tangerine sequined dress by Christian Dior. Orange is not one of Blair’s usual colors, but I really dig it; it pops well against the “Breakfast at Tiffany’s”-themed bridal shower decor. It’s interesting because the dress itself is from Fall 2008, which means it’s not quite “vintage” enough for the 2011 airdate. I’d be curious to hear why Blair is wearing a dress several seasons old when, at this point, she was typically wearing stuff straight from the runway. —– Of course, between the bow and the sequins, you know I love it anyway. Because of where the bust sits, it rather naturally gives the illusion of a pregnant belly (or a good shape for someone trying to disguise one). She pairs it with the ballerina clutch from VBH and a pair of platform heels, both in an incomprehensibly ugly greyish-nude snakeskin. I can’t figure out why you’d do that to this gorgeous dress! —– The makeup is good! I love the matchy-matchy lip, and the cat-eye is sleek. I also like the updo; pearl earrings are a bit predictable here, but this is season five so, we’ll go with it. You know you love me!

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What is the process behind dissecting BW’s outfit?

I do a lot of Internet research! At the time it was airing, it was so popular that fashion and celebrity websites would document the outfits on the show, especially Serena and Blair’s. There are also great credits to be found on Pinterest. I usually have a starting point—I’ll remember a certain dress was Marc by Marc Jacobs, for example—and I’ll Google around with different combinations to find other credits. Also, there are great Poshmark and eBay shops that stock items worn on the show, so they’ve been great resources. And Tumblr! There used to be an active community of fans on Tumblr, so I try and comb through their archives.



How has Blair’s sartorial choices informed your own?

Well, Blair got me way into headbands, for sure, both then and now. I cannot tell you how thrilled I am that hair accessories are making a big comeback. Sometimes I’ll try and curl my hair like hers too, but that’s a fool’s errand with my hair so it’s rare. I’d say the biggest influence is that I lean into dressing really feminine and pulled together, trying to color-coordinate stuff or find a fun accessory to make an outfit pop. I think maybe that’s not the coolest way to dress today, but it makes me happy.


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Hello Upper East Siders, and welcome to another #WaldorfWednesday! It’s weirdly challenging to find truly spring lewks from Blair, I think because the show would have stopped filming in late winter/early spring when things still would be chilly in New York. But I like this look from season two’s “The Wrath of the Con” in which Blair gives Georgina a very Waldorf makeover to try and trick Poppy into admitting she scammed people by pretending she’s a Texan oil heiress. (You had to be there.) —– The foundation for the look is this “Yasmin” floral blouse from Diane von Furstenberg, and it’s REALLY hard to tell, but there are baby pops of yellow in there – remember that in a minute. It’s a very deep cut, so it comes with a matching tank top layer underneath to keep things classy. Her pink tweed skirt is the “Ainsley” style from Tibi (can you imagine Tibi making something like this today?) and truly, the giant bow across the front is a Boss Move. —– She accessorizes with white tights — I think I’ve made my feelings on that clear here — and yellow pumps, plus some pearl jewelry and a bow bracelet that looks like a Rachel Leigh “Audrey” style worn by B in blue in episode 2×02. Every shot of Blair Waldorf makes me want to bust out my curling iron and a good lip gloss. You know you love me!

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What’s your favorite Blair Waldorf fashion moment, and what about it works so well?

This is such a hard question for me. I still think one of my all-time favorites is the brown Marc by Marc Jacobs dress from the first season’s Thanksgiving episodes. I might be biased because, a) Gossip Girl always did fantastic Thanksgiving episodes and b) that episode, “Blair Waldorf Must Pie,” is a top five all time Gossip Girl episode. It was so feminine—the bow motif on the tights! I had a pair just like them from Forever 21 that I wore until they were completely torn up—and honestly, so uptight, not a curl out of place, that I think it said so much about Blair and what she was going through in that moment, which is the genius of great costume design. There’s a great moment in the episode where Dorota is helping her get dressed and she says, “With pearls,” to indicate Blair needs a pearl necklace, and I love that moment. Eric Daman was just so brilliant on this show.


But, because I’m just completely obsessed, let’s round out the top five: this Moschino dress from season four in Paris, this Catherine Malandrino dress from season two, this Marc by Marc dress from season one, and this Alice + Olivia dress from season two. I think. Ugh, wait, can I get a top ten?!


Are there any more recent shows in which fashion plays a primary role that you think Gossip Girl has informed?

I think Gossip Girl changed the game in terms of what was expected from these glossy teen shows, for sure. I can’t imagine what The O.C. would be like if it had come after Gossip Girl. I mean, that show already had crazy Chanel and stuff, but I feel like Marissa Cooper especially would just be over-the-top insane. It also made it acceptable for these high-fashion brands to loan out to television, which I think was more game-changing than anything else. Obviously it owes a huge credit to Sex and the City in that regard, but Gossip Girl became this huge, highly-papped phenomenon in the digital age, which opened brands’ eyes to the power of television.

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