Little J’s style has definitely evolved over time. | Photos: Pacific Coast News

Welcome to round two of our look back at Gossip Girl’s most iconic fashion moments. Excited? You should be.

Today I’ll be walking you through the style evolution of Jenny Humphrey, played by the always-controversial Taylor Momsen. From sweet little freshman to edgy goth designer, to Constance Queen Bee, Jenny’s transformation was the most dramatic of any character.

And, okay, I’ll admit it: I was sort of glad to see her go after season 4. Those ripped fishnets, frayed extensions, and hissy fits got really old really fast… but of course, now that she’s gone, I actually miss her. Thank goodness she’ll be back for Monday’s series finale!

Below, we’ll take a look at Jenny’s style transformation over the course of the series, and show you how to get her most iconic looks.

Table of Contents

Little J

Coat, Skirt, Blouse, Cardigan, Tights, Socks, Pumps, Headband | Photo: The CW

Our sweet little Jenny started off at Constance as Blair’s most willing minion. Desperate to be popular (and usurp the throne), she pretty much dressed exactly like Blair, but with a more girlish twist. (Not that that’s a bad thing! Imitation is the sincerest form of flattery, after all.)

Pair a plaid skirt with a short-sleeve pussy bow blouse, and voila, you’ve got your very own Constance uniform. Add a Jenny spin with an adorable pair of polka dot socks layered over opaque white tights. Since we’re going for sweet and innocent, add a soft, candy-colored pea coat. Next, prove you’re a worthy minion by sporting a Blair-approved navy headband. Add a bright red cardigan and matching pumps and you’ll definitely be invited to sit on the Met steps. Just don’t sit too high.

Rebel Yell

Dress, Leggings, Jacket, Booties, Clutch, Bangles, Earrings | Photo: The CW