I’m back again with some more Gossip Girl outfit rankings, and this week we’re focusing on the Upper East Side’s Bad-Girl-Gone-Good-Gone-Bad-Again-Back-To-Good-Then-Bad- And Oh I Give Up Who Knows, Serena Van Der Woodsen.
Serena’s personality is the antithesis to Blair’s, and so is her style. Whereas Blair was all high fashion all the time, Serena’s looks are often a lot more relaxed, fitting with her carefree personality. Consequently a lot of her outfits are very, very similar, and often quite boring. Serena is neither my favourite character nor my favourite style inspiration, especially in season one, but although in this season she’s usually just wearing some combination of leather jacket and boots she does manage to strike out with something different sometimes (with varying results).
Here, then, are all of Serena Van Der Woodsen’s outfits from season one ranked from “I snooze” to “I would die to own that dress”.
Enjoy, and remember that the same rules apply here as they did for Blair’s outfits – no pajamas, no underwear or bathers and no outfits from film homages.
62
There isn’t anything particularly offensive about this, it’s just ranked lowest on the list because it’s essentially just a sports uniform, and it’s nowhere near as uh … interesting … as Blair’s, so it ends up in bottom place here.
61
Ugh, those mid-calf length saddle tan leather boots are the most 2007 thing I’ve ever seen. I had some pretty much identical to this around that time. I think the outfit would look so much better if they were just a bit taller.
60
Both the shirt and the coat look like something you’d pick up really cheap from a Target, which does not fit Serena’s luxe aesthetic at all. The lemon yellow is also just a really unflattering colour for Serena’s hair.
59
Eric’s expression in this screenshot pretty much sums up how I feel about this outfit.
58
This outfit, the top especially, looks like something a mum would wear.
57
Blair had a similar problem with one of her outfits, but the main thing wrong here is just the lengths of the different items. Individually they aren’t so bad – I quite like the coat, actually – but together they’re a mess. The boots are too long for the coat and the un-tucked top gives Serena’s torso a weird proportion. If the top was tucked in and the boots were shorter, this whole look could be saved. It would be a Christmas miracle.
56
I just really hate those orange gloves. They look like they are part of a superhero costume. I also think the jacket looks like something you’d find shoved into the back corner of an op-shop.
55
A perfectly “meh” outfit. The colour of the top is flattering.
54
Unlike Blair, I actually think Serena’s hair looked really nice with this outfit. The outfit looks alright standing up but the jacket bunches weirdly when she’s sitting down and I honestly just think that’d really annoy me, so I’ve ranked it lower than it probably should be.
53
Ugh, this is a mess. Too much pastel makes the whole outfit look washed out, those boots look like hideous 1960s sci-fi film rejects and don’t get me started on how ugly that snake necklace she’s wearing is – and the fact it’s completely wrong for an outfit like this. My eyes.
52
Everyone needs a quality leather jacket in their wardrobe. Or, if you’re like Serena, you need about fifty of them.
51
This whole outfit is giving off very Edie Sedgwick vibes, and I like the leopard print coat, but the dress looks really cheap.
50
Cardigans with interesting details, like the shoulder details on this one, elevate a simple outfit into something more special.
49
I’m a sucker for stripes but those mid-calf boots strike again!
48
Poor Serena had the worst outfit for the masquerade ball. I like the combination of yellow and black, and I think her hair looked amazing, but the makeup made her look frumpy and her mask was just really unflattering. The whole look managed to transform Serena from the beautiful butterfly she normally is into someone raiding their grandma’s dress-up box.
47
I quite like the matching boots and jacket, actually. Didn’t think I would, but I do. The red scarf is a great contrast to the skirt and really helps the outfit pop.
46
More great leather jackets and a super punky Avril Lavigne-esque tie. Love it.
45
I know I complained a lot about the mid-calf length boots but I actually really love these ones. The rest of the outfit is snooze-ville, though.
44
Aah, the iconic pilot ep outfit. Love the jacket, love the stripes, HATE the scarf.
43
This outfit is alright, but the colour scheme seems a bit too washed-out.
42
Punky Avril Lavigne-esque tie version two – this time with punk Avril Lavigne-esque pins!
41
Not only is this outfit kinda boring but it makes me feel hungover.
40
Something I never noticed before is that this cardigan is actually Dan’s, worn by him in an earlier episode. I’m giving the outfit extra points for cuteness.
39
Not only do I love the layered necklaces here, I love the aesthetic of studying in layered necklaces. These rich kids honestly never stop, do they?
38
The sparkle adds an interesting element to this outfit, elevating it above ordinary.
37
I really like the pattern on this dress. The colour scheme is a bit so-so, but the pattern saves it.
36
A great necklace and a great overall colour scheme.
35
I think this is probably my favourite of Serena’s endless leather jacket supply. I love not only the beautiful red color but the interesting cut of the jacket.
34
I re-he-heeeeeeaaaally love those shoes.
33
Yellow and black can make you look like a bumblebee or it can make you look absolutely gorgeous. There is no in-between.
32
2007 really was the year of those sleeveless little vests for layering, wasn’t it? I love this one.
31
All of the different shades of grey here are really working in harmony.
30
Serena’s version of this dress is nicer than Blair’s (maybe that’s just because orange is my favourite colour), but I think it would have looked even better paired with black heels.
29
Both the cut and the colour of this dress is lovely. Could have done without the necklace, though.
28
The material of this dress is just so whimsical and lovely.
27
Serena looks great in grey but this dress does look a little bit like a nightie.
26
Serena should have worn more purple because she looks great in it. The outfit is even better because of those sheer tights.
25
I wish Serena wasn’t wearing the leather jacket on top because the one she is wearing underneath is lovely. That fringed bag is also amazing.
24
The deep colour of this dress works well with Serena’s golden locks. I also love the layered necklaces. It’s all a very Gothic kind of look.
23
The coat is so bold and bad-ass, as are the red socks layered over the tights for a pop of colour.
22
I love this outfit’s soft boho vibe. Look at the floral motif on the heels of the shoes!
21
It’s a bit hard to see in this screenshot but one of the necklaces that Serena is wearing here is a little golden bird, and my love for that necklace alone earns this outfit this spot on the list. The dress itself is also very nice.
20
I think this top is just so cute and pairs so nicely with these jeans.
19
I feel like nobody else in the world would suit the vibe of this dress as much as Serena.
18
Not quite as good as Blair’s, but still a great coat none-the-less. I love colourful outerwear.
17
This sweater-dress ensures that not only can you be warm, you can look great doing it.
16
I’ve basically been obsessed with relaxed blazers ever since I saw this outfit.
15
Serena is honestly a vision in this gown. There is so much I love about it that I don’t even know where to begin – the colour, the pattern, the details… ahh, we could be here for hours.
14
The dark colours of this outfit really help that gorgeous headscarf to pop, pop, pop!
13
I think bracelet sleeves are one of the most fashionable things a coat can have. I also love the layering of these earthy browns and different textures.
12
I love this dress! I don’t know what more to say except I love it!!!
11
The pattern of this dress is really interesting, and it’s a very flattering colour.
10
I love the pattern and colours of the top and I think it goes really nicely with the belt and the cardigan.
9
The ultimate rebellious school uniform.
8
It’s a pale colour but it doesn’t make Serena look washed-out like some similar colours do.
7
This outfit has so many interesting and complimentary details. I especially love that necklace.
6
Another amazing gold coat! This outfit is especially good because of the striking contrast created between the black and the white materials.
5
The date might have started off badly but at least Serena got to wear one of the best dresses in the show.
4
What I like most about this dress is its simplicity. It’s kept interesting by the studded detail at the bottom.
3
I love this top. I had one similar and was devastated when it was ruined by some errant soy sauce. I don’t think Serena would ever be as clumsy as me, however.
2
This dress is absolutely stunning. I love the colour, the cut and the material. I also love how Serena treats expensive items like this as if they’re just regular casual clothes, pairing it with a pair of woolen tights as if it’s nothing.
1
The ultimate season one Serena dress. It’s cute, it’s boho, it’s probably incredibly expensive. That’s Serena’s style in a nutshell.
More like this: I Ranked Every One of Blair Waldorf’s Outfits So You Don’t Have To (Season 1 Edition)
