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Gossip Girl: Jenny Humphrey - Recreate The Makeup Looks Of Your Favourite Upper East Siders

Updated: Aug 2, 2019

Disclaimer: This article contains spoilers for all 6 seasons of Gossip Girl

Hey Upper Eastsiders, Gossip Girl here. And I have the biggest news ever

It's time to pull out your headbands because Gossip Girl is returning for a 10 episode on HBO's new streaming service in 2020. I am a huge fan of Gossip Girl so when I heard the news I knew I had to create a Miss Makeup post about it (or should I say 3?). The next 4 Miss Makeup posts are dedicated to Manhattan's elite our Queen B Blair Waldorf, Serena Van Der Woodsen, Little J (Jenny Humphrey) and Vanessa Abrams. Each product will feature 5 of the characters most iconic makeup looks, steps on how to recreate the look and recommended products (some which the shows makeup artist actually used on the actresses when filming the show!)

All images courtesy of Netflix/The CW unless stated otherwise

Look 1: Jenny's First Appearance (Season 1, Episode 1)

Our innocent Little J is first seen at Grand Central Station with Dan, coming home to their dad Rufus. If only we knew who she would turn out to be in the next few seasons...


- Lightly dust a peachy blush on the apples of the cheeks

- A medium coverage foundation or BB cream will work as a natural and youthful base


1. Dust an icy white shade along the entire eyelid

2. Using windshield wiper motions to brush a nude brown eyeshadow into the crease

3. Brush the same shade along the outer corner from the middle of the lid

4. Tap a shimmery white shade into the tear duct

5. Dust the same shade along the brow bone

6. Use the same brown shade from earlier to wing the eyeshadow down to the lower lash line

7. Coat lashes in a brown mascara


- Dab a hot pink lip gloss from the centre of the lips to the outer corners

Look 2: Little J's First Taste Of Royalty (Season 1, Episode 14)

Near the end of the first season, Jenny starts to dress more like the other Constance students on the Upper East Side. Her makeup becomes bolder and her clothes start to look more expensive. In this episode in particular she has taken over Blair's spot as Queen B. Yes it's the episode where she dumps the yogurt on Blair's head.


- Apply blush to the apples of the cheeks and lightly on the forehead to balance the look

- Concealer under eyes and dot the concealer along the nose, chin and forehead


- Use natural brown and beige shades for the eyeshadow look

- Apply a thick charcoal line along the lower and upper lash line using eyeliner


- Apply a pink lipstick

- Dab a clear gloss over the lipstick for Jenny's glassy look

Look 3: That Photo Shoot With Agnes (Season 2, Episode 8)

After befriending Agnes, Jenny started to make some questionable makeup and outfit decisions. She went from preppy to grunge in a matter of episodes. This episode had one of Jenny's wildest moments when she swapped outfits with Agnes at a bar and took part in that out of the blue photoshoot.


- A simple base of foundation, concealer and blush will allow the eyeshadow look to pop


- Don't be shy with the eyeliner and mascara for this look

- The bolder and more pigmented the eyeshadows are the better

- Charcoal grey and shimmer eyeshadows are recommended


- Apply a clear or nude lip to balance with the eyeshadow look

Look 4: Her Cotillion Date With Nate (Season 3, Episode 9)

Jenny really upped the glam for her mature cotillion look. The episode begins with the minions suggesting guys that Jenny should take ask her escort. But after a drama filled series of events she ends being escorted by Nate Archibald (pictured to the right of the first image)


- Apply a decent amount of red or pink blush that will be brought out by the lipstick colour

- Brush a deep bronzer across the forehead and cheeks for Jenny's glowing skin


- Draw a thick line on the lash lines using a charcoal black eyeliner pencil

- A mix of silver, grey and shimmery eyeshadows are essential to replicating this look


- Apply a pigmented red liquid lipstick for this bold lip look


Recommended Products:

- Milani Baked Blush: Dolce Pink (Source of the first image)

- Sephora Collection Long Lasting Eyeliner: Black (Source of the second image)

- Bobbi Brown Nude Lip Gloss (Source of the third image)

- BYS Eyeshadow Palette: Smokey (Source of the fourth image)


I hope that you enjoyed reading this post as much as I enjoyed writing it. I love being able to write about beauty looks from Gossip Girl characters so expect many more articles about them soon. Who are your favourite characters and what other makeup looks should I write about?

To read more Gossip Girl related posts check out our 'Gossip Girl' section on the Blog page or click the links below

Blair Waldorf:

You know you love me

- xoxo Miss Makeup

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