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 OutfittersUrbanOutfitters - NEW LOGO 88x31. Pick up technicolor bags, bright tights, and the most colorful trench coat you can find for maximum Jenny appeal.

Hats

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 Beckersurf.com 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:

Filed Under: Fashion Tips / Tags: , , , ,


25 Responses to “How To Dress Like Jenny Humphrey”


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

    Kristy - June 5th, 2008 at 10:30 pm

  2. 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

    Lily - June 6th, 2008 at 12:27 pm

  3. 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)
    Thanks!

    carly - June 6th, 2008 at 3:34 pm

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

    melissa - June 6th, 2008 at 3:38 pm

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

    micha - June 6th, 2008 at 9:12 pm

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

    sarah - June 8th, 2008 at 1:20 pm

  7. 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!:)

    lauren - June 9th, 2008 at 6:31 pm

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

    thanks a LOT!!!!!
    LUV YA…. :)

    ezyra - June 10th, 2008 at 11:24 pm

  9. 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! :)

    Briana - June 11th, 2008 at 10:00 am

  10. [...] How To Dress Like Jenny Humphrey (9) [...]

    How To Dress Like Georgina Sparks - June 16th, 2008 at 9:01 am

  11. 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.

    Julie - June 23rd, 2008 at 6:44 pm

  12. 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?

    Jessica - July 9th, 2008 at 4:07 pm

  13. 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!

    Linda - August 18th, 2008 at 5:25 am

  14. 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.

    elle - August 30th, 2008 at 10:38 pm

  15. 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?

    victoria - August 31st, 2008 at 10:57 pm

  16. 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!

    Alycia - September 1st, 2008 at 3:51 pm

  17. love your site. thanks.
    and love gossip girls.

    sandra - September 25th, 2008 at 10:10 am

  18. 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?
    http://www.hollywoodtoday.net/wp-content/uploads/2008/04/gossipgirlcast-2.jpg
    i love them soooo much<33 lol, thank you!!! ((((:

    hanna - September 25th, 2008 at 6:32 pm

  19. 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

    Inès - November 2nd, 2008 at 8:35 pm

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

    MIsstigri - November 4th, 2008 at 9:37 am

  21. 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.

    Haylee - November 6th, 2008 at 4:36 am

  22. I agree with Haylee

    MIsstigri - November 10th, 2008 at 3:03 pm

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

    Katya - November 12th, 2008 at 6:17 am

  24. 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

    Jordan Marie - November 12th, 2008 at 4:24 pm

  25. 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!

    Briana - November 12th, 2008 at 6:34 pm

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