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.

Table of Contents

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