How to Dress Like Jenny Humphrey

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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:

37 thoughts on “How to Dress Like Jenny Humphrey”

  1. 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!:)

  2. 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?

  3. 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

  4. 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

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

  6. 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!”

  7. 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.

  8. 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???

  9. 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.

  10. 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! 🙂

  11. 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


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