Style Guide [Jenny Humphrey]


Although her character seems to have gone downhill this season, Jenny Humphrey has always been my favorite dressed character on Gossip Girl. I think her best style moments were at the end of Season 2 and the beginning of Season 3. Now at the season finale of the 3rd season, her hair extensions have gone out of whack and make up is far too dark and dramatic. But previously, I think she looked stunning in amazingly put together ensembles and lighter but still bold make up. So this is my guide to dressing like Jenny Humphrey in her prime.

Many people tend to confuse Jenny's style with that of the actress who portrays her, Taylor Momsen. Although its clear that Taylor's rock and roll style [she's got her own band, The Pretty Reckless] has influenced her character's style, there is a clear difference between the two. Jenny's style is more refined but still keeps that rebel chic edge, while Taylor's is more grunge and sometimes very provocative.

Elements of Jenny Humphrey's Style:

1. The Leather Jacket.
This first element is an absolute must. Jenny is rarely seen not rocking a leather jacket. While there are many cuts and styles for leather jackets out there, such the bomber jacket or more of a blazer cut, Jenny always works a motorcycle-cut leather jacket. With it's usually double-breasted lapel, more fitted shape, and excess amounts of zippers and buckles, a leather moto-jacket adds that tough girl edge to Jenny's look.

While her minions are seen wearing metallic or red versions of this jacket, Jenny usually sticks to the classic black leather. If she isn't in a black leather jacket, she's either wearing a dark gray leather moto-jacket, a dark denim moto-jacket, or a black leather moto-vest. If its humid where you live I suggest wearing the vest version and if you are weary of harming animals in the process of wearing leather, there are many convincing faux-leather jackets out there or you could find a denim jacket with the same cut.

2. Textures in Black.
Jenny wears predominately black clothing most of the time, but she keeps it interesting by incorporating different textures of black into her look. Whether it be black sequins, black lace, black fishnets, black satin, black ruffles, or black leather, she mixes a variety of materials to give her ensembles a more luxe feel. For more formal occasions she tends to glam things up in black sequin dresses. On an everyday basis it seems she always wears black sheer, lace, or fishnet stockings. By never wearing flat solid head to toe black, she adds more dimension to her outfits.

3. Layers of Grey.
It seems as if Jenny always has on at least a dozen layers on a casual day. She tends to throw on gray knitted scarves over gray thick bulky sweaters over thin gray tees or tanks and tops it off with gray ribbed beanies and gray fingerless gloves. This element of monochromatic gray is simple to make work because all values of gray will work together, which isn't true for different shades of black. The use of gray creates a neutral canvas for anything else she adds on top. An easy way to mimic Jenny's look is to start collecting an assortment of gray cardigans, tops, and winter accessories. Throw them on without over-thinking it too much to get Jenny's laid back almost effortless look.

4. Red & Blue.
The only deeply saturated colors Jenny wears are red and blue. The blue element is usually attributed to her Constance School uniform, but you can still incorporate navy blue in other ways. Jenny's school outfits barely even seem like she's wearing a uniform at all. At a very close glance you can see the sliver of a blue school tie or a hint of a navy blue pleated skirt. Her Cotillion dress had strips of dark blue worked into the black. Sometimes she is more bold with blue when she works in blue plaid scarves or royal blue ankle boots into her look. While blue is usually the backdrop for her outfits, Jenny uses red as a bold punctuation. A deep red skirt or a blood red bag adds a pop to her ensemble and adds an accent to anything else she is wearing.

5. Muted Pink & Green.
For more dressier occasions when Jenny gets a little bored of her dark ballgowns, she opts for a very muted, almost beige pink or a very light, mint green. An easy way to get Jenny's style if you don't already wear a lot of black or dark clothing is to pull a dress you currently own in one of these shades. Jenny keeps these two otherwise very springy colors from looking too innocent or girly by pairing them with dark make-up and tough-girl accessories.

6. Jenny's Silhouette.
Each girl on Gossip Girl has her own body feature she plays up. For Serena, its her bombshell curves and tall stature, for Blair its her dainty waist and hourglass figure, and for Jenny its her thin frame and mile long legs. On an everyday basis, Jenny tends to wear very short hemlines with tall heels to show off her legs. She keeps from looking too immodest by wearing looser baggier layers up top. She doesn't have the assets that Serena has, so wearing bigger clothes up top fills her out more. That way the attention goes directly to her barely there skirts and legs that never seem to end. For formal events, Jenny does break out some very form fitting frocks, but because she doesn't have as much as Serena, it doesn't come off as too revealing.

7. Ankle Boots.
This girl seems to perpetually wear high heeled ankle boots 24/7. Sometimes they are metallic and sometimes they are gray, but most of the time they are black. Jenny has a variety of different types of ankle boots. Some lace up the front, some have zippers, some have studs, and some are peep-toe, but all of them have at least a 4 inch heel and go up to right below her ankle. A quick way to add some of Jenny's rebellious edge to your look would be to go pick yourself up a pair of simple black ankle boots. Places such as Aldo, Steve Madden, and Topshop have plenty of Jenny-worthy options.

8. Studded Bags.
While no one can forget that bold purple Valentino bag Jenny wore first season, the third season Jenny seems to always carry a bag made of black leather and covered in metal accents. All of her bags have a very slouchy unstructured shape to them and sport silver spikes, gold studs, or lots and lots of chains and zippers.

9. Mixed Jewelry.
There is an old fashion rule that states that metals should never be mixed when it comes to jewelry. Silver goes with silver. Gold goes with gold. Jenny Humphrey clearly does not follow this guideline. In addition to mixing gold and silver, she throws in rhinestones, pearls, and black beads. Layering jewelry is a must for this girl. With necklaces usually she combines thin silver chains with dainty gold pendant necklaces and strands of pearls. If she isn't wearing many necklaces, she puts the emphasis on large bold dangly earrings or chunky random stacked cuffs.

10. Heavy Makeup & Bleach Blond Hair.
Nicknamed 'Raccoon Eyes' Jenny definitely lives up to her title. On most occasions, Jenny is sporting extremely dark eye makeup. However, unlike the second season Jenny, whose raccoon eyes were the work of thick black eyeliner or black matte eyeshadow, Jenny has moved on to create her raccoon eyes from glossy deep plum, gray, or burgundy eyeshadows. The trick to Jenny's new look is to not concentrate the shadows on the rims of the eye, but to cover the entire eyelid in a soft wash of shadow. Also the eyeliner should be extremely subtle and the eyelashes extremely evident. A lengthening and thickening mascara should do the trick.

My favorite look for Jenny is when she goes lighter on the makeup. When I say lighter, I mean a lighter shade, not a decrease in the amount of makeup she has on. Unlike the first season Jenny who barely had any makeup on at all, now Jenny always looks pretty made up. Her lighter look utilizes soft silver or creamy pink eyeshadows instead of dark hues. Overall her lighter makeup looks kind of dreamy and compliments her pale skin.

For the lips, Jenny usually has very dark lipstick on. Towards the end of the third season, her lips were a kind of matte zombie-esque purple tone that I wasn't a fan of. The girl looks much better with bold red glossy lipgloss or sheer nude lipstick on.

While its a rule to always only emphasize one feature with makeup, the eyes or the lips, Jenny doesn't really follow this guideline either. She'll wear dark eye makeup with dark lips, dark eye makeup with light lips, light eye makeup with dark lips, and sometimes light eye makeup with light lips. The combination I favor the most for Jenny is light silver eye makeup with heavy bold red lips.


I absolutely loved Jenny's lighter curlier hair at the beginning of the third season. She no longer had plain boring Serena-wanna-be golden blond hair or that choppy mullet cut. The perfect hair moment for Jenny was when she first claimed her role as Queen at Constance. Her hair was a respectable length 5 or 6 inches past her shoulders, it looked full and voluminous, and her bangs looked perfectly in place. Later unfortunately her roots always looked a little greasy and her hair extensions looked too long, thin, and ratty.

For Jenny's best hair, I would suggest:

1. First blow dry your hair and take especially good attention to the way your bangs fall.
2. Create a side part and spray your hair with some sort of curl holding spray.
3. Clip up the top half of your hair to reach the bottom layer thoroughly.
4. Curl each .5 inch piece of hair at a time with a 1 inch barrel curler.
5. Let the top half of your hair down and repeat step 4.
6. Flip your hair over and finish with hairspray.

Hope this entry was helpful in evaluating Jenny Humphrey's style and that you feel inspired to incorporate a few of her elements into your wardrobe. Be sure to watch more my next entry which will present many outfits inspired by Jenny and demonstrate the elements I have described here. Until then!


[Photo credits:


  1. Stunning post, darling!
    Love her style, especially all those booties!


  2. This was a great post, thought it also made me boil with anger inside. I hate Jenny Humphrey! I miss innocent little J, not this self-pitying bitch who has no sense of her own actions that she's become.

    I do enjoy pieces of her wardrobe from time to time. Mostly the (lol) leather jackets and the shoes. Oh, and that YSL Roady.

  3. What a comprehensive list you've put together here! I totally agree that her extensions are ridiculous now, but she has always had the best style on Gossip Girl.

  4. This was one amazing post girl! Loving how you described her style so accurately! And I'm totally with you, Jenny was an amazing style icon in the show, I don't know what's up with all this black/dark make up and almost goth style she's baring lately. =)


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  6. Oh boy. This girl's legs are just to die for.

  7. wow she does have some great styling in the show.. haha but must admit not a huge fan of her, although i do love the outfits and they look really good on her!


  8. oh and HER "style" that is ... ;)

  9. oh I love her jackets and red lips!

  10. thank you so much for your comment!
    I really like Taylor Momsen's style!


  11. WOW. What a fantastic post! Well-done.

    I've always kind of liked Jenny's style, even as she started to enter her "angsty teenage rebellion stage" (as I will now call it). My friends hate it, but there's this rad edginess to it.

    Thanks so much for stopping by!

  12. Great post! very detailed. I love her just got out of bed hair waves. I wish my hair looked like that.

    Checking out your blog, very cute! I'm now following. Please check out (and hopefully follow) my blog as well.


  13. I have officially given up on watching Gossip Girl! It was too dramatic for me, haha. But I love this post! Jenny's the underdog, and she's got such badass style.

  14. Since I never watched Gossip Girl I had no idea who Jenny was but glad I read this post.She has this rockish attitude and her style is so creative.Leather jackets are my favorite and I love the grey beanie.
    Tokyo and Seoul Dreams

  15. sh looks cute
    i like her outfits she looks amazing

  16. oh i love her outfits too she has a perfect mix of rocker-edgy but hot.

    would love you to visit Passport Glamour & follow if you like

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    enter the giveaway!

  17. woww you have made a great report! you have such a great blog! I'm following you! :)


  18. OMG, thank you for this heaven!!! I adore her style, all signature items are my faves also - jackets, booties, black and grey... total love!

  19. This has to be the best post I've seen on jenny's style, loved every bit of it! I found this of searching on google.

  20. Bookmarking this because though I'm not a huge fan of Jenny's character, I've always loved her style, especially when she started to break out from the girl who was trying to fit in in the first season. When she started being herself, you saw the transition in the way she wore clothes as well! Great post, doll. :) I really love this.


  21. do you know what kind of ray-bans she wears in #4 Red and blue the first photo?

    I love the post! I've been trying to match jenny's style for a while know and I love how in depth your style profile was. I'm only sad that I found it so late!!

  22. Jenny's style is inspiring and I love it. I adored her style since season 2 and as the seasons go by her sense of fashion has gone extreme. Everything she wears from top to bottom is awesome however I do stress that most of the clothing that she wears are over the limit of most budget, it doesn't change the fact her clothing are the best! Although her makeup can be over the top, everything from top to bottom is amazing I love her hair, jewellery and especially the clothes!!

  23. Awesome blog, I loved Jenny season 2 and 3, and the stylists on the show are very talented to create such different looks (Blair and Jenny- polar opposites) but still be very on trend with the current styles. I love love love how they dressed Jenny- the love affair starting when she started rockin' the mullet, her personal style changed so much. Then her season 3 style was a huge inspiration for my own style finishing up high school and moving out into the world- you worded it perfectly with rebel chic.

    By far the best post I've ever found on Jenny's style :)

  24. a very great post, i really love jennys style in he third season, esspecially her hair, wioch I found bad in the second one.


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