Another week, another Gossip Girl outfit ranking. This week’s focus is on Jenny Humphrey (arguably the worst Gossip Girl character, but Vanessa is close behind – more about her next week!)
Out of all of the characters in Gossip Girl nobody changes their personal style as much as Jenny Humphrey does. Even within the eighteen episodes of the first season we see her outfits go from eccentric thrift pieces to refined Imitation-Waldorf and back again. This style evolution mirrors a personal crisis that Jenny has throughout the season, where she is desperate to fit in with the rich girls and carve out an identity for herself.
Here then are all of the outfits that she wears in season one, ranked from “boring” to “not bad, Little J.” As always I didn’t bother with pajamas and things like that – a lot of Jenny’s outfits in this season are boring enough as it is. Enjoy!
46
There’s nothing much to say about this outfit. It’s literally just a plan singlet. Let’s move on to something more interesting.
45
I like all the constituent parts of this outfit, I just don’t like them all together. I don’t think the pink coat looks very nice with the green tights, and the shoes are just too much.
44
When Jenny put this dress on for the first time she said “I don’t feel right” and I have to agree. This just isn’t a nice dress at all.
43
The little jacket is cute because I love houndstooth, but the rest of it is pretty meh.
42
I really like this top and think it’s really cute but my god is that brooch ugly. I can’t focus on anything else except how much I want to set destroy that brooch under my shoe.
41
Who relaxes at home in gold jewellery like this?
40
Vanessa got this gown for Jenny from a theater or something and it really does look like a costume. An ugly one.
39
This hoodie is really cute.
38
I love these pants. I used to have a pair almost exactly like them but they got old and broke. RIP to those pants I loved so much.
37
This coat is pretty nice and I don’t even mind the pattern-mixing all that much.
36
You see, I like this dress – I think it’s a really nice colour and material. But are those straps part of the dress or are they bra straps? It’s been nearly 15 years and I’m still demanding answers.
35
No wonder Blair didn’t want this dress and gave it to Jenny. It’s pretty boring. I like that necklace though.
34
The reason this outfit is here on the list is because I have absolutely no opinion about it, in contrast to some of the other outfits that have elements that I actively hate about them.
33
Generic school outfit but really cute shoes.
32
I like the colour and the embroidery detail of this top.
31
More lovely houndstooth.
30
The dress is nice enough but the best part is that gorgeous accompaniment… the burgundy coat (Nate’s pretty nice too).
29
Silver and yellow is an interesting colour combination. I quite like it here – the piping isn’t enough to overdo it.
28
This dress verges on being a bit 2007 for my liking but I do really like the colour of it and the flowing skirt.
27
I love this coat – the flower applique detail on the collar is a work of art. However, Jenny wears this coat a lot this episode (for thematic reasons) and there are nicer outfits featuring it. I do like the bold red of the blouse, though.
26
I think the pattern and colour of this dress is nice but it also looks a bit too much like a Sunday craft project Jenny whipped up on her sewing machine.
25
This dress also looks like something Jenny made on her sewing machine in five minutes but I like the material so I’ll give it a pass. The red belt also accessorizes it really well.
24
Another dress made by Jenny but this one doesn’t look like a craft project. It’s sleek and stylish and still looks just as good today as it did back then.
23
I just think denim overalls are really cool.
22
I love pretty much everything about this outfit – the cute dress and even cuter tights, the necklace, the jacket, the boots. It’s funky without being over the top. Also I never thought I’d use the word “funky” in 2021 but here we are.
21
I think Jenny probably has the best necklaces out of anyone in this season. Here’s another good one.
20
And another good necklace!
19
Because she’s a Humphrey Jenny is legally required to wear plaid at least 20 times in a season, but when the pieces are this nice that’s not a law that’s difficult to follow.
18
The material of her bag is the thing I like most about this outfit.
17
I just think this outfit looks so warm and cozy. I love the colour scheme too.
16
This is hands-down the best jumper on the entire show.
15
See, I told you there were nicer outfits with this coat. I think it looks much nicer when not paired with something bright red.
14
I think that the belt is a stylish way to tie all of the elements of this outfit together.
13
I’m not a huge fan of boot-cut jeans, but I have to admit that these ones really work with this outfit. That jacket also has such a lovely flowing shape.
12
Love the necklace (remember how I said Jenny has the best in the season?) and the blue looks great with her hair colour.
11
Red is a great colour to pair with the rest of this outfit.
10
This coat is such a delight! I could make some comment about it being like a ray of sunshine (because it’s yellow, get it?) but I’ll spare you that.
9
It’s that lovely blue coat again, this time with an equally lovely scarf.
8
I love the mixing of patterns and colours on this dress. It looks so fun and summery and pretty!
7
Pink and blue pastel is always a winning combination. I wonder where everyone on the show gets those super bright tights. I’ve literally never seen any for sale before?
6
I love that plaid jacket but also look at that bag! It’s fitting that Jenny’s in a gallery right now because that bag deserves a place in it.
5
I love clothes with interesting details, like patterns or cut-outs. The pattern on this is so cool!
4
I’m a sucker for any red outwear – coats, cardigans, hats, you name it, I love it.
3
See? Look how fantastic this coat is! And those double gold headbands are the perfect accessory.
2
This dress is gorgeous. I wonder if those floral appliques were put on by hand?
1
I love the cut and the colour of this bolero cardigan so much. It works so well with the skirt and the tights. Sometimes the colour combinations of Jenny’s outfits can be too much but everything here is working together in perfect harmony.
More like this: I Ranked All of Blair Waldorf’s Outfits So You Don’t Have To – Season 1 Edition
