Gossip Girl Fashion: How to Dress Like the New Jenny

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The new Jenny Humphrey from Season 2 of Gossip Girl

I wrote an article about how to dress like Jenny Humphrey earlier this year, but I’ve received tons of emails from you guys wanting an updated version of that article covering Jenny’s new style. As requested, here you go..

Last season on Gossip Girl, Jenny Humphrey didn’t have a distinct style – she mostly dressed like the other girls at school and struggled to fit in. For Season 2, Jenny has a whole new look and has become quite the little fashionista! I’m sure most Gossip Girl fans would agree that she’s looking chicer than ever, rocking a new haircut, lots of eye makeup, and some fabulous new clothes.

In this article you’ll learn everything you need to dress like the new Jenny: her fashion must-haves, how to emulate her style, and even how to get her hair and makeup looks.

Jenny’s New Style

There’s a lot that goes in to the Jenny’s new look. As an up-and-coming fashion designer still under the age of 18, she wants to look sophisticated, fashion-forward, and maybe just a few years older than she is. But Jenny can’t afford a wardrobe filled 100% with designer clothes so she makes most of her clothing herself.

Now you have to remember that this is Gossip Girl we’re talking about, which means Jenny’s exact wardrobe probably costs thousands of dollars. But you can get her looks for less if you understand the basics of her style!

Jenny’s New Fashion Essentials

Last season, Jenny was trying to fit in with the most popular girls at school, so she loved preppy headbands, long coats, and anything designer. These days, Jenny has a more unique style that’s one part rocker chick and one part cutting edge fashionista. Here’s a list of her fashion must-haves:

1. Plaid, Plaid, and More Plaid

Jenny from Gossip Girl wearing plaid

Jenny obviously has a favorite print! Plaid is a hot trend for fall, which explains why Jenny has been rocking plaid constantly in almost every episode this season. As a budding fashion designer trying to prove herself and network in the fashion world, it’s a must that she keep up with the hottest runway trends.

This season, Jenny has been wearing lots of plaid dresses, but she’s occasionally worn a plaid jacket instead. If you want to emulate her style a plaid dress should be top on your list. Pair the dress with dark opaque tights, ankle boots, and a couple of large faux-diamond necklaces and you’ll have Jenny’s look down.

2. Grey & Black

Jenny Humphrey wearing dark colors like grey and black

Grey and black have become two of Jenny’s new staple colors, part of her more sophisticated new look. Shades of grey are basic, minimalist, and ever so New York City chic. Even better: they can be mixed and matched with everything else in your closet!

From her seemingly-vintage leather jacket to her prim and proper grey tweed bolero, Jenny loves to wear black and grey jackets. But she also looks just as chic in a plain heather tee and funky necklace.

As you can see from the pictures, basics don’t have to be boring. Staying within black and grey shades can actually be a chic way to dress. Just make sure to dress up your outfits with some great accessories – we’ll talk more about that later in the article.

3. Pops of Bright Pink

Jenny on Gossip Girl wearing dresses with hot pink

Along with her plaid dresses and shades of grey and black, Jenny has been known to throw in a pop of hot pink to her outfits this season. Last season she wore pops of yellow and purple, but this year it’s all about neon magenta.

An easy way to add a pop of hot pink to your outfit is with a hot pink pashmina scarf like the one Jenny wore in the leftmost photo above. Right now I’m in love with the cashmere scarves from Pashmina International – they’re incredibly soft and cozy! I can picture Jenny wearing this pink & black scarf ($30.25) with a black and white outfit.

Another way to include hot pink in your wardrobe is by wearing a neon pink tulle skirt under your regular skirts like Jenny does in the center photo above. You can find tulle skirts on ebay for next to nothing, or learn how to make one yourself!

4. Piles of Accessories

The new Jenny Humphrey on Gossip Girl loves to pile on accessories and jewelry

The old Jenny Humphrey would have accessorized with a bright colored handbag and a cute headband. The new Jenny, on the other hand, piles on the jewelry and takes a more rock and roll attitude with her accessories.

I love the look of Jenny’s layered necklaces – it’s so easy to do with a few inexpensive pieces from Charlotte Russe or H&M. Get a few necklaces of different lengths and materials – a few beaded ones, a metal one with some bling, and whatever else catches your eye. Then mix ’em all up and wear them together for an effortlessly chic accent to any outfit. Same goes for bracelets – stack them on however you want and pretend it was totally random.

5. Hats

Jenny from Gossip Girl wearing a hat

Jenny wore lots of hats during Season 1 of Gossip Girl, and she’s continued to rock them in Season 2. In the first picture, Jenny is wearing a knit tam hat for a hippie-chic vibe. In the second picture she’s rocking an ultra-trendy bowler hat.

If you’re looking for a slouchy beanie, this one from Forever 21 is a cute option, as well as this one. If you want a hat that’s similar to Jenny’s in the second picture, look no further than the Forever 21 Ribbon Trimmed Derby Hat – a carbon copy of Jenny’s look for only $16.80!

Jenny’s New Hair and Makeup

Jenny's new hair cut on Gossip Girl

Probably the biggest change in Jenny this season has been her drastic new haircut and dark, smokey eye makeup. Fans seem to either love it or hate it, but very rarely is there anyone who thinks her new look is just “meh.” If you love it, learn how to get the look below.

Jenny’s New Haircut

For season 2, Jenny traded in her long, wavy blonde hair for a shorter, choppier shoulder-length style with heavy bangs. It’s a dramatic look that definitely isn’t for everyone.

If you’re tempted to copy Jenny’s hair style, make sure you will look good with bangs! They aren’t for everyone, and can make some face shapes look wider or less attractive than normal, so cut with caution. If you aren’t sure whether or not bangs are for you, check out this guide and always consult a trusted hairstylist before you go through with it.

How To Style Your Hair Like Jenny

For Jenny’s hairstyle, all you need is the right haircut (see the paragraph above) and a good quality ceramic flat iron. With flat irons you get what you pay for – the more expensive ones damage your hair less and produce better results. I recommend the CHI Turbo, HAI and FHI which are all excellent choices and available on eBay for less than retail price.

Step by step:


Use a good quality protective hair spray or a product like Biosilk Silk Therapy, available at Beauty.com.


Blow dry your hair until it’s completely dry. This is very important – don’t ever straighten wet hair! A hot flat iron can actually BOIL your hair, causing more damage than any conditioner can fix.


Starting at the bottom layers of your hair and working up, use your flat iron to press small sections completely straight.


Finish with a spritz of hairspray.

Jenny’s Makeup

Jenny Humphrey's Makeup

While it looks complicated, Jenny’s new makeup look is actually very easy to achieve. Start with a blank face – use foundation and concealer if you need it to cover any imperfections. Next, apply a loose powder to get rid of any shine. Then apply a peachy pink blush like NARS Orgasm to the apples of your cheeks.

Now for the smokey eye.. start with a wash of shimmery grey eyeshadow like Mac’s Knight Divine from your lash line and into the crease of your eye. Next, apply a thick line of dark black eyeliner on the upper and lower lash lines and on the inner rims of your eyes. Grab a q-tip and smudge this line to get it looking smokey, then blend it with some more of the original grey eyeshadow. Keep blending until you have the desired look, then apply two coats of black mascara.

Finish this look with a nude lip gloss. The focus here is your eyes, so a lighter lip color will balance it out. There you have it – Jenny’s makeup look in a few easy steps.

Your Thoughts?

Now that you know how to get Jenny’s new look, I want to know what you think of it. Do you like Jenny’s makeover, or did you prefer her old style? Would you wear this look yourself?

I want to hear your thoughts, so be sure to leave a comment!

*Photos courtesy of TaylorMomsen.org, The CW, and Taylor-Momsen.net

108 thoughts on “Gossip Girl Fashion: How to Dress Like the New Jenny”

  1. In some of her photes she look stunneing but in others she look horrible but at the moment loveing the new look x woop woop x x

  2. We have Gossip Girl in Germany, too. I like Jenny, and her new style I tried to copy it but here in germany you didn’t were normaly something like that. And you must be very skinny to wear close shorts. Her style is real rock chic something like the old Mischa Barton

  3. well i must say i love jenny 🙂
    she is my favourite and plus she is the one with best taste in fashion, i mean like serena and that have good fashion but not as good as jenny (L)’s her work, i have so many dresses just like hers… ilys it! very much.
    and the goth style is cool, i reckon it suits her well 🙂 and im just like her i must say.
    you no you love me xo xo gossip girl.

  4. i owuld like to see the new new jenny its not as much goth the style were she has the long hear and dresses with a match or serena and blair

  5. Wow, she really, really, really looks like Joan Jett with that hair, clothing and make-up! Only two things parting them is the age and the haircolor!

  6. ehm hi , look do you guys have NOTHING better to do than sit here & say tht her eyes look like raccoons , seriously nearly every comment critising her is the same , so tbh yous should just shut up , i love the new jenny ecspeically her hair & make-up . in a few weeks im getting my hair like tht . i love her clothes aswell
    bye (: !

  7. i think her new look is awsome. i luv the way her eyes look. her clothing is awsome too. all in all she rocks the look.


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