I’ve watched Gossip Girl a lot. I’m not ashamed to admit it. I’m going to watch the hell out of the new series as an absolute guilty pleasure.
There are many things to love about the soapy series, from its fancy soirees to the absolute balls-to-the-wall bonkers plot-lines (Bart Bass coming back from the dead, anyone?). The best thing about Gossip Girl is the fashion, however, and no character is more fashionable than Blair Waldorf, the Queen of the Upper East Side who we all loved to hate at first and then we came to love.
Blair’s style in season one can be described in one word: preppy. Blue, red and white makes up the bulk of her wardrobe, along with ballet flats, gorgeous coats and of course her iconic headbands. But with so many amazing looks, which ones are the best?
Well, wonder no more, as I’ve done the hard work for you and gone ahead and rated all of Blair’s outfits from season one from “meh” to “I would do anything to have this exact outfit in my wardrobe right now.”
Just one point of clarification before we begin: I omitted any outfit that was based on something from a film (like the Breakfast at Tiffany‘s outfits) because they aren’t outfits created just for Blair and as such I thought they couldn’t be fairly judged against her other outfits. I also omitted pajamas, underwear and bathers, as they can’t be judged against actual outfits and therefore would all be at the top of the list anyway.
Enjoy!
67
This outfit is just ugly on so many levels. The colours don’t go together at all, the headband looks like either a weird scarf or snakeskin??? (either way, both things Blair wouldn’t ever choose) and the hair just seems wrong too. All-in-all, this is the worst outfit of the season, and one of the worst in general for Blair (although the absolute worst is in another season, so just you wait for that!)
66
This outfit is just boring, and I hate the combination of colours. [Miranda Priestley voice] That’s all.
65
The perfect outfit for when you’ve got to write an apologetic essay to your principal at 3, then head to work at Wall Street at 4.
64
The main reason this outfit is so low on the list is not so much because of the dress itself (it’s just fine, really), but because I hate the hairstyle so much and I never want to remember how every girl looked like this in 2007 because it still haunts me.
63
The green headband doesn’t fit with the purple and grey tones of the rest of the outfit. The dress and turtle-neck are pretty cute, but the coat looks really cheap and like something you could buy from Target.
62
Too many polka-dots. I can understand how this outfit is attempting to be “cute”, but again: Too. Many. Polka-dots.
61
Blair is supposed to be known for her cutting-edge sense of fashion. I suppose she forgot about that when she put this outfit together.
60
I just hate the shoes in this outfit and no I cannot explain why. They just make me weirdly uncomfortable.
59
The perfect outfit for a funeral! Too bad she’s planning a get-together with friends.
58
I like the gold necklace over the black turtle-neck, and her hair is gorgeous.
57
I actually like this dress better than the one Blair’s mum tells her to wear to the Kiss on the Lips party. It’s simple and classic and the detail around the waist make it interesting. You shouldn’t have listened to Eleanor, Blair!
56
I like the shoes but it’s a bit weird to wear a jacket and tie to a party, isn’t it?
55
I just have one question: why are you wearing a belt like this to do sports?
54
The reason why I don’t rate this outfit super highly is because the length of the everything seems off. Either the jacket needs to be shorter or the skirt does. Is that just me? Do you all see what I’m seeing here?
53
I don’t think this outfit is inherently “bad”, there are just so many other better variations of them (red tights, blue skirt/shorts, white shirt) in this season that I’ve put this one pretty low on the list.
52
Honestly I just think this dress is just really boring. The colours are meh, the pattern and material are meh, the style is meh. It’s worn during a flashback, not a dream sequence, but I’d understand if it was a dream sequence because this dress is putting me right to sleep.
51
I don’t like the length of the cardigan, and it feels like there’s just too much going on in this outfit. The textured tights, the ruffles, the necklace, the belt, the heels… argh, it’s exhausting!
50
Just take that coat off and this outfit would instantly be 100% better.
49
This is such a Badass Bitch outfit and I love it. Replacing the fascinator with sunglasses was literally an earth-shattering moment for Teenage Me.
48
I think some small improvements could make this outfit better. I’d get rid of the white pearls and change the eye-makeup to silver instead of gold. I think the dress is cute, especially with the little bow detail, but it’s really the styling that’s dragging it down.
47
I love the cape and the headband. It’s aaaaalmost too much with all the different patterns but it just works. Just.
46
Hair? Amazing. Coat? Gorgeous. Belt? Stunning.
45
It’s an interesting pattern on the dress. It’s also nice to see Blair in something less preppy for once in this season.
44
This outfit honestly really divides me. On one hand I adore the leather coat, and think it’s one of the Baddest Bitch things Blair wears in this entire season, but I really, really hate the boots. So. Much. They aren’t bad enough to ruin the whole outfit, but I unfortunately can’t rate it higher because of them.
43
The pattern on the dress is so interesting and I love the shoes too. I definitely don’t think this is an outfit that would work for many, but because it’s Blair of course it does.
42
My favourite thing about this outfit is the hair and the shoes (the latter of which unfortunately aren’t in the picture but are pretty much the best shoes ever featured on Gossip Girl).
41
I think the pink cardigan looks really good with the light blue top. The shorts would have been better if they were high-waisted, but it was 2007 so nothing then was high-waisted. I guess I can forgive it.
40
The red and blue work really well on this outfit. I wish the shoes were red, though. Can’t you just imagine that? Wouldn’t red shoes just be perfect?
39
This outfit is a great example of Blair’s preppy style in this season, but there are still better ones.
38
The outfit looks much better with the necklace Blair gets later on in the episode, but before that it’s kind of boring. As the Queen of Over-Accessorizing it’s kind of weird to see Blair without even a pair of earrings.
37
I think this is a really nice outfit, but it’s not a Blair outfit. Blair wouldn’t wear plaid like that, nor jeans. The whole thing is too casual, and it honestly seems more like something season 1 Jenny would wear instead. 
36
If you’re going to get stood-up by your “friends”, at least you can look great whilst doing it!
35
As the seasons go on, Blair wears more and more pencil-skirts. This is one of the first she wears, though, and it sets the precedent. I love the muted colour-tones of this whole outfit.
34
This is a nice dress, but it’s the shoes that really make this outfit something more special.
33
This outfit is styled for a clothing advertisement but I think it works as an outfit in its own right, especially for someone like Blair.
32
I’m a sucker for anything orange, especially a dress with a pattern as cool as this one.
31
This dress is okay, but it would be better without that giant bow. Sorry, but I rate Serena’s dress more than this one of Blair’s.
30
This is all such a Look with a capital “L”.
29
This is such a pretty dress. The way it sparkles reminds me of the ocean at night.
28
I know this is an outfit for a specific purpose (in this case ice-skating) but I think it’s lovely none-the-less. I actually own a skirt nearly identical to this one because I loved the one Blair wears here so much!
27
My favourite thing about this outfit are the details. The bracelet sleeves on the dress, the black lace trim, the texture of the material, the lace-patterned tights… I could go on and on.
26
This outfit is a preppy dream.
25
All of the navy and red here almost borders on Too Much but it works.
24
I would die for this coat. Straight-up just die for it.
23
Everything about this outfit is really pretty and dainty.
22
If you’re going to rock up to a party without an invitation this sure is the outfit to do it in.
21
One of the first outfits we see Blair wearing in the show, instantly encapsulating her prim-and-proper aesthetic.
20
I love all of the different lace working together in harmony on this outfit.
19
I know I said before that Blair Waldorf doesn’t do jeans, but I think they really work here. It might just be me being totally blinded with love for that green jacket, though…
18
The yellow coat works so well with the darker colours of the rest of the outfit. When Blair forays into colours beyond navy and red, she does a good job. This whole outfit just pops!
17
The green coat is to die for and all of the colours in play here really compliment each other.
16
The gold details on the cardigan really elevate it to something special, as do the ruffles on the shirt.
15
I think the top is really sweet and I like the layering. The green shoes also transform it from being something too casual for Blair.
14
This dress is an icon, amongst the best in Blair’s wardrobe. Styling it with black tights and headband also ensures that the white lace really pops.
13
The pattern of the dress would be enough to land it this top spot, but then there’s the hair, which is perfection (and which I spent an unfortunate amount of time trying to replicate when I was younger).
12
The BOOTS. The TIGHTS. I am in HEAVEN.
11
The mixture of patterns here really works because they are similar colours, and the cardigan ties it all together nicely. I also love the sparkly detail on the cardigan – it’s these interesting things that can turn something rather mundane, like a white cardigan, into something special.
10
This is a perfect Christmas outfit: festive with the gold, white and red without being in your face about it.
9
I love the contrast between the black and white stripes and ruffles and the red cardigan. Both pieces compliment each other so, so well.
8
Everything about this outfit works so well. The blue shorts, belt, tie and piping on the shirt is brought out brilliantly against the white shirt. I also love the necklace as it turns this from a regular preppy school outfit into something more high-society.
7
I love the pattern on this dress and the softness of the colours. I also think this is one of Blair’s best headbands this season.
6
I love everything about this outfit! The dress is one of my favourites of Blair’s – I love the colour and the little bow detail. I also love the coat, and think it goes perfectly with the dress, not overshadowing it at all. I also love the hair and the headband! *Chef’s kiss*
5
What a delightfully divine dress! Who cares about being jilted by Chuck Bass when you’ve got this outfit to wear!
4
My favourite thing about this outfit is actually the shoes – I think those ruby-red sandals would make even Dorothy envious! They pair so nicely with the dress, which is such a flattering style and lovely colour.
3
My favourite of Blair’s dresses from season 1! I’m still as envious today as I was back then that I don’t own it myself. I love the colours, the details and those short sleeves. It’s the epitome of Blair’s 60s-inspired style – what a gorgeous outfit!
2
I love this coat so much. The bell sleeves really set it out from the rest, as does the colour and the black piping. I’ll search until the end of my days for a coat just like this one.
1
Not only is this the best outfit that Blair wears in the first season, it’s one of the best outfits she wears across the entire series. I don’t think anything encapsulates her preppy style better than this outfit, and I’ve spent at least half of my life tracking down the various components of it for myself. I remember the first time I saw this episode I did my hair exactly the same as this the next day, and Blair’s style has been an inspiration to me ever since. This is it. This is the one. The best of Blair Waldorf’s outfits (for season one at least).
More like this: I Ranked All of Serena Van Der Woodsen’s Outfits So You Don’t Have To (Season 1 Edition)
