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Gossip Girl Fashion – Seasons 3 & 4: Jenny Humphrey



The past few weeks, I’ve been working my way through our original Gossip Girl fashion series to create updated breakdowns of each character’s style from Seasons 3 and 4. And while each character has evolved since Seasons 1 and 2, I think it’s safe to say that little Jenny Humphrey has had the most dramatic style evolution.

In the first season of Gossip Girl, Taylor Momsen’s character was just trying to fit in with the Upper East Side girls she went to school with. Without the funds to wear designer pieces like Blair and Serena, Jenny made her own clothing and did her best to emulate Blair’s style on a budget.

In season 2, Jenny transformed her look with some new style choices. The youngest cast member adopted a rocker chic aesthetic, with dark makeup and a choppy hair style – a transformation that marked the start of Jenny’s love affair with controversial styles.

Jenny’s New Style

These days, the character Jenny Humphrey’s style is a slightly toned-down version of Taylor Momsen’s real-life style. Little J pushes the envelope with super-short dresses, knee-high boots, fishnet stockings and dramatic makeup. All though some of her choices may be a little too over-the-top for an everyday outfit, her style is definitely inspiring.

Jenny’s New Fashion Essentials

Over the past few seasons, Jenny’s style has definitely changed, and so have her closet staples. Gone are the days of school uniforms and plaid. In Jenny’s wardrobe, bright colors are now practically nonexistent. These days, instead of trying the emulate the affluent community that she went to school with, she uses fashion to rebel against them.

Oversized Sweaters

One of Jenny’s favorite go-to pieces is an oversized sweater – usually in a shade of gray or black. A loose sweater is a super versatile piece – wear it with jeans, leggings, tucked into a skirt – the options are endless! Lately Jenny has been a fan of long sweaters worn with fishnet tights and boots (a little scandalous, but sure to garner you some attention).

Product Information: ModCloth, Forever 21, Forever 21, Urban Outfitters

Rock n’ Roll Touches

A major element of Jenny’s style is the rocker accessories and fabrics that she weaves into every outfit. Whether she’s rocking zebra print, a tight leather skirt or a biker jacket, her looks always have attitude. These fitted pieces also work perfectly to balance out her oversized cardigans and sweaters.

Product Information: Forever 21, Forever 21, Forever 21, Revolve Clothing

Finishing Touches

Accessories are perhaps the most important element of Jenny’s scandalous look. She wears dark, subdued clothing – so she uses these “finishing touches” to really attract attention. Jenny’s most important accessories are tights, boots and dramatic makeup. She loves to show off her legs with detailed stockings and unique heeled boots, and rocks plenty of black eyeliner at all times. When she isn’t dressed up, she is also a fan of flat combat-style boots which really epitomize the rocker look.

Product Information: Zappos, Endless, Nordstrom

Jenny’s New Beauty Routine

Since Season 2, Jenny’s hair has undergone a major transformation – from choppy layers to long and straight (and platinum blonde!). Her hair is almost always down with messy waves or crimps towards the ends. Unlike the other Gossip Girls, Jenny doesn’t try to look perfect and put-together.

As for her makeup routine, Jenny tends toward the extreme. Below, I’ve tracked down some great how-to videos to help you get her dramatic look!

Tying it All Together

Jenny Humphrey has gone through a significant style evolution over the last four seasons, as most high school students do! Although her look has become a little scandalous, there’s no arguing that she is confident enough to know herself and her style. She’s a great inspiration just for her risk-taking attitude alone.

Your thoughts?

What do you think of Jenny’s new and old styles? Would you wear the outfits that she’s been wearing so far this season? Do you think they’re appropriate? Jenny is one the the most controversial stars on the show – I want to hear what you guys think! Be sure to leave a comment.

Posted on on November 15, 2010 / Filed Under: Inspiration / Tags: , , , , , , , , , , , , , ,

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26 Responses to “Gossip Girl Fashion – Seasons 3 & 4: Jenny Humphrey”

  1. 1
    November 15th, 2010 at 2:03 pm

    People give Little J so much flack, but I love her. She’s my favorite female character (Chuck being my overall favorite). While I think Taylor dresses too over the top in her daily life, for the most part there are pieces of her “new” Jenny style that I like. I almost wish she’d go back to more of her Season Two look and hair, because now she has those fake extensions. She used to be such a pretty girl, but the costume department is covering her up (not enough with clothing, too much with makeup).

  2. 2
    November 15th, 2010 at 2:15 pm

    I own and love the second Forever 21 sweater. soooo cozy. Love the insight on more ways on how to wear it!

  3. 3
    November 15th, 2010 at 2:30 pm

    I dressed up as jenny humohrey for halloween hah

  4. 4
    November 15th, 2010 at 3:14 pm

    Great post! I like jenny’s style best in seasons 3 and 4!

  5. 5
    November 15th, 2010 at 3:33 pm

    The oversized sweaters makes me feel like Jenny/Taylor has an eating disorder. She looks way too skinny nowadays. And the corpse style makeup doesn’t help. I miss the old Jenny style from season 1

  6. 6
    November 15th, 2010 at 4:00 pm

    i love both the new and old jenny! i try to make my style a very toned down version of her look.

  7. 7
    November 15th, 2010 at 4:35 pm

    I like her-both old and new-she’s just pretty!

    Jordan, FYI, the costume/makeup department is not exactly who to blame since this is basically how she wants to dress/make up. Taylor/Little J in season 1 is the image her old manager wanted her to be. I believe she fired him and that’s why she now can dress like a real her.

  8. 8
    November 15th, 2010 at 4:36 pm

    I like lil J’s sweaters because they look so cute and comfortable but she did not change her style that much.

  9. 9
    November 15th, 2010 at 4:58 pm

    While I love gossip girl, I hate their use of hair extensions! I think Jenny style changed in the show because she wanted to promote herself as a singer. Little J should looks less like Madonna and more like Carolina Herrera in my opinion.

  10. 10
    November 15th, 2010 at 5:17 pm

    Not mad about her style, but I love the items you picked out!

  11. 11
    November 15th, 2010 at 5:30 pm

    While I generally think Taylor Momsen dresses inappropriately, I think you did a really good job using her general style and pieces of her style. I think if one were to choose just one aspect of her style, it could totally work (rather than wearing all of them at once).

  12. 12
    November 15th, 2010 at 5:57 pm

    By far she has did a 360 I dont like her style now its a little to much for her age its not even Goth I’m just loss for words her style just got a little rebel with out a cause

  13. 13
    November 15th, 2010 at 6:11 pm

    While I love Gossip Girl, Jenny/Taylor’s fashion style is not an inspiration for me at all. She looks really inappropriate for her age and I only liked her in season one…looking forward to more GG inspired posts though. Maybe you could do Nate next kinda like the Chuck inspired post :)

  14. 14
    November 15th, 2010 at 6:30 pm

    While I agree with a lot of the comments about the age-appropriateness of her outfits, Little J is my favourite girl in terms of style.
    Her look is always fun and a little punky and that is the kind of style I love both myself and on other people.
    I think you’ve done a really good job of her style here :]]]
    I love her hair now too- it really makes me want to grow mine!!

    Charlotte xxx

  15. 15
    November 15th, 2010 at 7:43 pm

    I’m with Rin. Jenny’s – and Taylor’s – style is usually pretty trashy & inapprop, but I like the ways you chose to feature the good parts in more tasteful ways.

  16. 16
    November 15th, 2010 at 8:44 pm

    Yeahh I actually think that Jenny’s look is fine, Taylor’s in real life is just disastrous…. But one can really get a good inspiration out of this post!

  17. 17
    November 16th, 2010 at 1:09 am

    I love Jenny Humphrey’s7 Taylor Momsen’s Style :D It’s just awesome!

  18. 18
    November 16th, 2010 at 7:47 am

    I really, really wish i could dress like Jenny/taylor Momsen
    her style is amazing! but its too inapropriate for where i live (Dubai, in the middle east, a Muslim Country)
    plus i just dont have the guts
    I just keep stockpiling articles like this till i work up the nerve :D

  19. 19
    November 16th, 2010 at 10:33 am

    her hair is so much better than the old choppy haircut, but still, its too long and looks odd – would be much cuter and healthier with 6 inches cut off.

    i see no point to jenny’s character this season.

  20. 20
    November 16th, 2010 at 1:19 pm

    I totally love Jenny’s style. Mine is sometimes pretty similar to hers. Anyway I think both Taylor and Jenny have changed alot and not really in a good way.

  21. 21
    November 17th, 2010 at 12:07 pm

    The skirts are a little too short for my taste, but the breakdown of her style is totally wearable and that’s what I love about it!

  22. 22
    November 17th, 2010 at 2:07 pm

    You did a great job picking out similar pieces to hers, but no, just no. I’m a Jenny hater, sorry.

  23. 23
    November 19th, 2010 at 10:09 pm

    I don’t really like Jenny that much either. But I really liked her style in the first season. After she went for the rocker look, I didnt like it much because it is just not the way that I would dress.

  24. 24
    November 22nd, 2010 at 5:55 pm

    I never really noticed her outfits in the 3rd season because I was so grossed out by her hair.. True story. Why won’t she just chop off those long, icky parts??

    I liked her style in both season 1 and 2. Cool clothes, healthy hair.. Miss those days!

  25. 25
    December 3rd, 2010 at 6:18 pm

    I just LOVE her new style! It is so awesome! I would deffenetly wear it1 ;]

  26. 26
    August 17th, 2012 at 10:40 pm

    She’s the upper east side edgy queen, and I really love her style in season 3! Some people criticize her hair and make up, but I think it looks great on her… well, maybe the makeup is a little over the top. But I hate that they doesn’t give Jenny enough importance in the story… I wanted to see Jenny in her paper of new constance’s queen, breaking hearts… living high school, not fighting over Nate Archibald… pfff

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