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How to Dress Like Jenny Humphrey


Gossip Girl's Jenny Humphrey, played by Taylor Momsen

For the last and final part in College Fashion’s Gossip Girl Fashion series, I’m going to break down Jenny Humphrey’s style, and show you how you can easily dress like Jenny.

Jenny, played by actress Taylor Momsen, is the youngest main character on Gossip Girl. She’s the younger sister of the character Dan Humphrey, who was dating Serena van der Woodsen for most of GG’s first season.

Jenny lives in Brooklyn, and hates that she doesn’t have lots of money like the other girls at Constance Billiard School for Girls. Fortunately, Jenny has an eye for fashion and skills with a sewing machine. She’s the ultimate “look for less” girl, and that’s what makes her style so fab to talk about here!

Jenny’s Style

As a high school freshman trying to fit in with uber-rich and fashionable juniors, Jenny’s style is very trend-conscious, yet still affordable. If Little J. can’t buy a designer gown for one of the exclusive parties, you can bet that she’ll show up in a gorgeous replica that she made herself. She’s all about finding designer knockoffs or creating them herself. She’d never wear anything vintage or “last season.”

If you want to dress like Jenny, take note of the latest fashion trends, and if you can’t afford a designer piece, make it yourself, or look for a similar item in a discount store. You also may want to pick up some of Jenny’s own wardrobe must-haves.

Jenny’s Fashion Essentials

Bright Colors

Jenny Humphrey from Gossip Girl's fashion sense: bright colors

Like Serena and Blair, Jenny loves to mix bright pops of color into all of her outfits. Brights were a huge trend this season, and Jenny took notice. Yellow was Jenny’s favorite color this season – from the yellow dress that she wore to __ party, to the yellow trench that she wore on a date with her new boyfriend Asher, she rocked it in nearly every episode. Purple was also big in Jenny’s wardrobe, in the form of purple tights and a purple Valentino purse (middle photo above).

To buy some bright stuff of your own, shop at Bluefly (fabulous accessories & shoes), Asiajam (crazy bright clothing at cheap prices), and for bright basics, Urban Outfitters. Pick up technicolor bags, bright tights, and the most colorful trench coat you can find for maximum Jenny appeal.


Jenny Humphrey from Gossip Girl wears lots of hats

Jenny is the only Gossip Girl cast member known for her winter hat collection. Since she loves plaid, her winter caps are always printed and usually match the rest of her outfit perfectly. Cute hats like Jenny’s are a great way to accessorize in the winter. If you want one of your own, try PacSun or Urban Outfitters during the winter.

Short Skirts

Jenny Humphrey from Gossip Girl wearing short skirts

Because she’s blessed with extremely long, skinny legs, Jenny loves to show them off with short skirts that hit above the knee. She pairs her minis with brightly colored tights in the winter, and bare legs when it gets warmer. For a casual look, Jenny accessorizes with a long jacket and flats or boots. If she’s going for a dressy outfit, mini dresses and skirts go with heels and fitted jackets.

If you want to dress like Jenny, designer mini dresses and skirts are all available at ShopBop , the ultimate online designer store. If you’re looking for something on the lower-end, I recommend both H&M and Forever 21.

Long Jackets & Coats

Jenny Humphrey from Gossip Girl (Taylor Momsen) Jackets

Jenny loves to wear a long pea coat or trench coat over her mini skirts and dresses. This is a really smart idea fashion-wise, because a structured, gorgeous jacket can make an otherwise boring outfit amazing. For example, in the middle photo above, Jenny wears a glittery gold patterned jacket over a solid-colored basic dress. Since most of the dress is covered up, the outfit becomes all about the coat.

A great long jacket is something you should spend a little extra money on, because it will last you many seasons and will work with so many outfits. For a classic jacket like one of Jenny’s, I recommend shopping at J. Crew or Ann Taylor for a basic trench, and Nordstrom for a flashier coat.

Prints & Plaids

Jenny Humphrey from Gossip Girl (Taylor Momsen) wearing prints and plaids

If you love to wear prints, then Jenny’s style is perfect for you. This girl is all about the patterns, paired with simple solid basics in coordinating colors. If you want to get Jenny’s look yourself,

For a similar cropped houndstooth hoodie (middle picture), try Karmaloop.

If you’re looking to cop a plaid jacket of your own, you can buy Burberry jackets at Nordstrom , or cheaper versions at Banana Republic . For the best selection of jackets, shop during late summer and early fall.

Your Thoughts?

What do you think? Is Jenny your Gossip Girl fashion icon, or are you more of a Serena or Blair? Would you wear Jenny’s style of clothing? Let me know what you think in the comments!

Also, if you missed any of the other Gossip Girl fashion articles, here they are in order:

Posted on on June 5, 2008 / Filed Under: Fashion Tips / Tags: , , , ,

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62 Responses to “How to Dress Like Jenny Humphrey”

  1. 1
    June 5th, 2008 at 10:30 pm

    Great post! But I wonder how Jenny can be a budget shopper who owns a Valentino purse. lol.

  2. 2
    June 6th, 2008 at 12:27 pm

    Thank you soooo much – i abso love jennys style. My wardrobe is based on her style and also miley cyrus’s because her dress sense Rocks!!! Do you think that you could do a dress guide for mileys too???? XoXo Lily

  3. 3
    June 6th, 2008 at 3:34 pm

    This is great!
    Do you know where that yellow dress is from?
    Also, where are the things from in the outfit(she’s wearing a polka dot dress with a jacket and a black purse)

  4. 4
    June 6th, 2008 at 3:38 pm

    Do you happen to know where the pink trench coat is from.
    It is under long jackets and coats.

  5. 5
    June 6th, 2008 at 9:12 pm

    i love your site, thank you so much!!!

  6. 6
    June 8th, 2008 at 1:20 pm

    this is really good! i wanna dress like jenny so this is a really big help :) thanks x

  7. 7
    June 9th, 2008 at 6:31 pm

    awe check out lil j :) i think she actually takes more style risks than most of the characters on the show. i can’t believe how young she is in real life.

    p.s. thank you for the wonderful opportunity from tjj maxx/marshalls. i seriously owe you one, i was so excited!:)

  8. 8
    June 10th, 2008 at 11:24 pm

    i love your site a lot….
    i love jenny’s style the most…..

    thanks a LOT!!!!!
    LUV YA…. :)

  9. 9
    June 11th, 2008 at 10:00 am

    Kristy – That’s a really good point, haha. Maybe it’s a knockoff? ;)

    Lily – Glad you liked the Jenny article, and I’ll see what I can do about MIley!

    Carly – Hmm, I don’t know where those are from, but I’ll check around and let you know if I find out.

    Melissa – I’ll look for it!

    Micha – Thank you :)

    Sarah – No prob, hope this helps!

    Lauren – I know, she’s only 15 or so, right? She easily could pass for 18 or older.. scary. And with the TJ Maxx/Marshall’s thing, no problem, anytime! Your blog is one of my favorites, and I knew they’d like it too! :)

    Ezyra – Thanks & you’re welcome! :)

  10. 10
    June 23rd, 2008 at 6:44 pm

    I know its summer, but will those knit tights be in style for the fall? (Pink Coat in Long Jackets) They look really comfy and not a uncomfortable and itchy as other tights.

  11. 11
    July 9th, 2008 at 4:07 pm

    Oh how I wish there were articles like this about The OC cast, even though it’s over. I liked Marissa’s style and Summer’s was also unique.

    Did you ever watch The OC?

  12. 12
    August 18th, 2008 at 5:25 am

    Love little J’s look! Especially when her hair changes from long, in the beginning of the season to short, towards then end. I love how she uses a bow with her hair tossled to one side! So cute!

  13. 13
    August 30th, 2008 at 10:38 pm

    she is my favorite character on the show, particularly because of her fashion sense. i think she dresses the best out of all the girls there.
    gahh i love her.

  14. 14
    August 31st, 2008 at 10:57 pm

    do you know if i would be made fun of for wearing bright colored tights and short skirts at school? would that be too dressy?

  15. 15
    September 1st, 2008 at 3:51 pm

    I love Jenny’s look!

    I was also (like Carly) wondering if you know where the bag is from in the photo where she has on the polka-dotted dress? I know I’ve seen it before, but I can’t remember where!

  16. 16
    September 25th, 2008 at 10:10 am

    love your site. thanks.
    and love gossip girls.

  17. 17
    September 25th, 2008 at 6:32 pm

    omg, i love this, you spent a lot of time on this ;o thanks a lot for this, it was amazing help, but do you know where i could get jenny’s tights in this picture?
    i love them soooo much<33 lol, thank you!!! ((((:

  18. 18
    November 2nd, 2008 at 8:35 pm

    I like this article ! But Jenny Humphrey has change and i prefer her new look . OH can you write an article about her new look ??

    Thanks & Bye

  19. 19
    November 4th, 2008 at 9:37 am

    Please can you talk about the new Jenny’s style. I think his black dress is amazing. She has beautiful wears.

  20. 20
    November 6th, 2008 at 4:36 am

    I personally don’t watch Gossip Girl like the rest of the world and I never will. Just recently I have seen some pictures of Jenny’s new style and I like it.I think you when you have enough time you should do an another article on Jenny’s new style.That would hella rad.

  21. 21
    November 10th, 2008 at 3:03 pm

    I agree with Haylee

  22. 22
    November 12th, 2008 at 6:17 am

    I think that you should do another ‘How to dress like Jenny Humphrey’ article considering the change in her style.

  23. 23
    November 12th, 2008 at 4:24 pm

    I agree with Katya!!
    I really want to see a picture of the outfit she was wearing at the end of the episode of her fashion show. The outfit she was walking down the street in all by herself carrying her sewing machine… The drapery outfit…
    Thanks, J

  24. 24
    November 12th, 2008 at 6:34 pm

    Wow, there seems to be a lot of you who want to see an article about the “new” Jenny! I’ll definitely start work on that. Look for it here soon!

  25. 25
    December 4th, 2008 at 11:56 pm

    For those of you who requested it, here’s an article on how to dress like the new Jenny!

  26. 26
    December 14th, 2008 at 4:48 pm

    I personally love jenny´s style, but think they should do another web on Jennys Style considering her new look.

  27. 27
    February 1st, 2009 at 4:16 am

    I absolutely LOVE her style!!!!! I like this style better than her new style though…
    Do you know where the pink trench coat is from???

  28. 28
    April 22nd, 2009 at 9:30 pm

    thanks for this! its great!

    i went into this store i dont normally go to, and i found this awesome plaid skirt that looks almost exactly like a skirt jenny wore in one of the episodes, only this one is purple. :]

  29. 29
    June 8th, 2009 at 3:23 am

    i like the new jenny MUCH betta bcos she is exactly like me. In fact im taking her picture 2 the hairdressers 2moro and getting her exact cut. i rly dnt like the whole ‘preppy’ look. its too colourful and i hav a lot of black and grey in my wardrobe. Also no offense but if i wore thi stuff in public i would look like a geek again NO OFFENSE.
    but the new season 2 jenny has her own style and no she has not got raccoon eyes.

  30. 30
    July 24th, 2009 at 8:38 pm

    You are probably the only person that really covers the character’s style. I pretty much dress like a mix of Blair and Jenny.

  31. 31
    September 23rd, 2009 at 8:36 am

    I prefer Jenny’s new style! Jenny just looked like another copy of “serena van der woodsen” in her previous style. She now looks like a dash of rock and roll chick with still the same sophistication to create the new look of “JENNY!”

  32. 32
    November 5th, 2009 at 8:39 am

    Grande piccola J!!!! Cmq ki è ke mi sa dire più o meno dove si possono trovare i vestiti alla jenny humprey??

  33. 33
    November 25th, 2009 at 4:24 pm

    hey does anyone know were i can get the plaid dress that jenny wears i love it!!

  34. 34
    November 30th, 2009 at 1:15 pm

    i loved this but could you do jenny in series 3! i love it PLEEEEAAASEE x

  35. 35
    January 1st, 2010 at 12:07 pm

    salut j’adore le style de jenny j’ai le meme meme je lui resemble

  36. 36
    January 5th, 2010 at 6:54 pm

    you can also try checking out this sure youll love it..they have lots of clothes worn by the cast of gossip girl.. especially blake,serena,jenny and vanessa

  37. 37
    January 10th, 2010 at 9:14 pm

    i really2x loveeeeee jenny’s rockin roll styles……
    am crazy bout 8,,,,,,,anyway,looks lyk avril lavigne
    has 8’s super tyt rival hahahahha………

  38. 38
    March 17th, 2010 at 12:09 pm

    were can i buy a cropped houndstooth jacket from in egland croydon?
    (gr8 article by the way)

  39. 39
    April 16th, 2010 at 12:25 am

    Great article

  40. 40
    April 18th, 2010 at 11:41 am

    hey u r totally right but 1 ting u 4got 2 mention dat jenny never wears the same ting twice !!! xoxo gossip girl (fan)

  41. 41
    April 28th, 2010 at 9:42 pm

    there’s a Longchamp bag like jenny’s from Rufus Getting Married on eBay now!

  42. 42
    May 29th, 2010 at 12:11 pm

    Jenny’s not like that anymore. she’s more into black clothing now.

  43. 43
    June 2nd, 2010 at 10:35 am

    Does anyone know where Jenny gets the “necklace” thing she wears with her uniform?

  44. 44
    June 3rd, 2010 at 11:34 pm

    Can you get pictures of all her outfits from season one ?
    I really love the way she dresses –
    Hit me up
    Thanks :D

  45. 45
    June 14th, 2010 at 12:09 pm

    i love this article. i tried the karmaloop place but couldnt find the cropped jacket so do u know any other places? thank you xx

  46. 46
    June 20th, 2010 at 8:04 am

    really great post xxx but as sarah says ^^^^^ do you know another place to buy the houstoooth jacket? cos the karmaloop place didnt have it

  47. 47
    June 21st, 2010 at 11:01 pm

    Holy crap, she used to look so cute.

  48. 48
    July 6th, 2010 at 9:09 pm

    good guide, but you forgot her staple fashion accessory: her high knee socks, as well as her tights! she wore those so many times from what i can remember in season 1! she was so much cuter season 1 rather than her rock n roll style in season 2 and 3. her style is kinda quirky but i love it!

  49. 49
    October 1st, 2010 at 5:29 pm

    love Jennys girl next door style, i like her new one better, but im more of a blair.
    —-<3—- arielle

  50. 50
    October 3rd, 2010 at 8:16 pm

    I miss the old Jenny when she wore vintage dresses since that makes her stand out. Her NEW style now is similar to Georgina and Jenny does not look good with black eye makeup. SHe looks like a raccoon.

  51. 51
    November 2nd, 2010 at 7:32 am

    Aw I had forgot how cute she was in the first season! Much preferered her character like this :-)

  52. 52
    November 17th, 2010 at 2:09 pm

    @Lottie: I completely agree! She was just so much more likable. Aw, old Jenny!

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