Skip to content

Kirsten Krupps

glitter mixed with rock 'n' roll

  • Home
  • About
  • Blog
    • Fashion
    • Beauty
    • Personal
    • Fitness + Health
    • Home
    • Marketing
    • Music
    • Photography
    • Food + Drinks
  • Shop My Posts
  • Amazon Storefront
  • Benable
  • Favorite Stores
  • Discount Codes
  • Contact
  • Home
  • About
  • Blog
    • Fashion
    • Beauty
    • Personal
    • Fitness + Health
    • Home
    • Marketing
    • Music
    • Photography
    • Food + Drinks
  • Shop My Posts
  • Amazon Storefront
  • Benable
  • Favorite Stores
  • Discount Codes
  • Contact
Fashion

How to Dress Like Jenny Humphrey from Gossip Girl

How to Dress Like Jenny Humphrey from Gossip Girl

Gossip Girl, the iconic television series that took us on a rollercoaster ride through the glamorous lives of Manhattan’s elite, has left an indelible mark on pop culture. While Blair Waldorf may have reigned supreme as the Upper East Side’s Queen Bee, another character who made waves with her unique fashion sense was Jenny Humphrey. With her fearless style and evolving looks, Jenny showed us that fashion is a powerful form of self-expression. Below, I’ll delve into the fashion secrets that will help you dress like Jenny Humphrey and embrace your own edgy, rebellious style. You’ll also find some Jenny-inspired items for your own wardrobe, both from the 2000s and more updated styles, as well.

THIS POST MAY CONTAIN AFFILIATE LINKS, WHICH MEANS I RECEIVE A COMMISSION IF YOU CLICK + PURCHASE SOMETHING. PLEASE VIEW THE DISCLOSURE POLICY FOR MORE DETAILS. THANK YOU FOR YOUR SUPPORT + HAPPY SHOPPING!

Embrace Edginess: Jenny Humphrey is synonymous with edgy, punk-inspired looks that evolved over the series. To recreate her rebellious style, incorporate leather jackets, studded accessories, and bold prints into your wardrobe. Fishnet stockings, ripped denim, and graphic tees are staples that can help you channel Jenny’s rockstar vibes.

Play with Layers: As Jenny’s character developed, so did her sense of style. She mastered the art of layering, often pairing unexpected items to create visually intriguing ensembles. Experiment with pairing oversized sweaters with tights, a mini skirt, and chunky combat boots. This juxtaposition of different textures and styles captures Jenny’s fearless approach to fashion.

DIY and Customization: One of the most appealing aspects of Jenny’s fashion sense was her knack for DIY and customization. Follow in her footsteps by distressing your jeans, adding patches to denim jackets, or creating unique designs on plain t-shirts. Let your creativity run wild and give your wardrobe a personal touch that’s reminiscent of Jenny’s inventive style.

GOSSIP GIRL, Taylor Momsen, ‘How to Succeed in Bassness’, (Season 3, ep. 307, aired October 26, 2009). 2007-. photo: Giovanni Rufino / © The CW / Courtesy Everett Collection

Footwear with Attitude: Complete your Jenny Humphrey-inspired look with footwear that exudes attitude. Think ankle boots, combat boots, and chunky platforms. These bold choices add an extra dose of confidence to your outfits, just like Jenny’s bold and audacious demeanor.

Confidence is Key: Jenny Humphrey’s style wasn’t just about the clothes; it was about how she carried herself. Embrace her confident, no-nonsense attitude when you wear her outfits. Own every look with self-assuredness, and remember that true style comes from within.

Photo courtesy of reddit.

Jenny Humphrey’s fashion journey on Gossip Girl showcased the power of self-expression through clothing. Whether she was sporting a preppy ensemble, experimenting with layers, or embracing her punk-rock spirit, Jenny’s style was a testament to individuality and creativity. By incorporating elements of her iconic looks into your own wardrobe, you can channel your inner Queen Bee and create a unique style that reflects your personality and attitude. So, go ahead and rock those headbands, layer on those textures, and own your edgy, rebellious fashion sense – just like Jenny Humphrey. XOXO.

P.S. If you’re wanting to dress like Taylor Momsen, the actress who played Jenny Humphrey, I’ve got you covered! See How to Dress Like Taylor Momsen from The Pretty Reckless here.

Shop Jenny Humphrey Inspired Items:

SHARE THIS
dress likeedgyfashiongossip girlJenny Humphreyoutfitrocker chicshopshopping
About Kirsten

About Kirsten

glitter mixed with rock n roll 🤘🏻 mother of dachshunds 🐾 marketer + photographer 📷 obsessed w/style, makeup, halloween, sushi, working out, + hp ✨ IL » ATX

Related Posts

Your Edgy Beach Vacation Capsule Wardrobe: What to Pack for Sun, Sand, and Style
Your Edgy Beach Vacation Capsule Wardrobe: What to Pack for Sun, Sand, and Style
Rock Your Summer: The Ultimate Edgy Capsule Wardrobe for 2025
Rock Your Summer: The Ultimate Edgy Capsule Wardrobe for 2025
How to Wear a Band Tee Four Different Ways
How to Wear a Band Tee Four Different Ways
Unboxing My FabFitFun Spring 2025 Box: Luxe Skincare, Chic Jewelry & More!
Unboxing My FabFitFun Spring 2025 Box: Luxe Skincare, Chic Jewelry & More!

Post navigation

Bridal Fashion and Accessories on Amazon: Bachelorette, Rehearsal Dinner, + More
Fall 2023 Fashion I’m Excited About

3 comments

  1. Pingback: How to Dress Like a Rock Star » Kirsten Krupps
  2. SSS Facebook says:
    February 1, 2025 at 1:55 pm

    Loved this post! Jenny’s style is such a fun mix of edgy and chic. I really appreciate the tips on how to incorporate her looks into everyday outfits. Can’t wait to try out some of these ideas!

    Reply
  3. OK WIN LOGIN says:
    May 2, 2025 at 12:00 pm

    I absolutely loved this post! Jenny’s style has such a fun mix of edgy and chic, and you captured it perfectly. I’m especially inspired by the suggestions for layering accessories. Can’t wait to try out some of these looks!

    Reply

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

About Me

About Me

Kirsten Krupps

Welcome to my rock n roll fashion and lifestyle blog. I'm pretty sure I was a rockstar in a past life and my sense of style derives directly from that. »

Shop My Posts

Follow Me on Instagram

NOLA, you were fun! We’ll be back to explore som NOLA, you were fun! We’ll be back to explore some more and eat some amazing food 🙌🏻 #nola #neworleans
a lil girls day is always necessary ✨ a lil girls day is always necessary ✨
🥂 🥂
POV: you drive a mini cooper #minicooper #minicoop POV: you drive a mini cooper #minicooper #minicooperconvertible #minicooperjcw #zestyyellowmini #zestyyellow #minicooperclub
Hanging out with the pups while supporting a good Hanging out with the pups while supporting a good cause… a great Saturday in my opinion @barksforbeers @divinecaninestexas
Meet Citrina 😜🍋‍🟩 #mini #minicooper #mi Meet Citrina 😜🍋‍🟩 #mini #minicooper #minicooperjcw #minicooperconvertible #zestyyellow #minicooperclub

Sign Up for the Newsletter

Get monthly tips, freebies, and sales delivered to your inbox.



Fashion

Beauty

Personal

Fitness

Home

Marketing

Music

Photo
graphy

Food
+ Drink

  • Legal
  • FAQs
  • Categories
  • Contact
Copyright © 2025 | All Rights Reserved | Fashion, Beauty, + Lifestyle Blogger in Austin, TX
Manage Cookie Consent
To provide the best experiences, we use technologies like cookies to store and/or access device information. Consenting to these technologies will allow us to process data such as browsing behavior or unique IDs on this site. Not consenting or withdrawing consent, may adversely affect certain features and functions.
Functional Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes. The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.
Manage options Manage services Manage {vendor_count} vendors Read more about these purposes
View preferences
{title} {title} {title}