We wrote an article about how to dress like Jenny Humphrey earlier this year, but we'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. We’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 weÄre 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:

Plaid, plaid, and more 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.

Grey & 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.

Pops of bright 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!

Piles of accessories

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.


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!

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