The Stunning Style Transformation Of Taylor Momsen

Taylor Momsen entered the spotlight at just three years old when she starred in the national commercial for Shake 'n Bake bread crumbs back in 1997. Of course, she is mostly recognized for her breakout roles as Cindy Lou Who in the 2000 film "How the Grinch Stole Christmas" and her character Jenny Humphrey in CW's popular TV series "Gossip Girl." Despite Momsen's promising career as an actor, the young teen had other plans in mind — namely, a vision that involved a mic in one hand and a guitar in the other. Momsen abandoned her acting career to pursue her dream of becoming a rockstar, which she realized in 2009 when she formed her band The Pretty Reckless, and with it came a dramatic style transformation that, to this day, surprises fans who still associate Momsen with her sweet character from "How the Grinch Stole Christmas."

That said, Momsen quickly removed herself from that angelic persona, as she is now known for her signature platinum-blond hair and lingerie-inspired rock and roll outfits. The actor has always shown a propensity for fashion, even before the raccoon eyes and platform boots era. "I grew up always needing to express myself," she once told InLove Magazine. "It's a constant need for an outlet for my imagination. Whether writing songs or creating a look, it's all about being creative and using that to express how I feel at any given time. Fashion is the outside appearance of my inner feeling. Or, I can use it to change my mood. It's fun for the imagination." As such, we're taking you all the way back to 2006 to see just how much Momsen's style has evolved over the years.

In 2006, 13-year-old Taylor Momsen attended the Warner Brothers Network All-Star Party wearing a red-and-gold Eastern-inspired ensemble with a chunky necklace and brunette hair. The former actor has naturally dirty-blond locks with dark roots, so her brunette hairdo wasn't a bad look at all. She resembled a young Michelle Trachtenberg — who has undergone her own stunning style transformation — due to her chocolate-brown strands and bright blue eyes.

However, her split with blond hair didn't last long, as she nabbed a major role in the cult-classic teen series "Gossip Girl." Following her work in various kids' films, such as "Spy Kids: The Island of Lost Dreams," Momsen landed her first grownup role in the CW show, where she played Jenny Humphrey or Little J. While attending a CW Network event with her fellow castmates, Momsen donned a floral pink minidress with silver jewelry. This was her pre-teen period, so her style at the time involved a wardrobe of girly dresses, pink lip gloss, and a light swipe of eyeliner. Spoiler alert: Momsen's girly phase ends here.

Everyone goes through an angsty teen phase, but they all pale in comparison to Taylor Momsen's complete 180-degree style revamp from cute little sister to adolescent Courtney Love. At the 25th Annual William S. Paley TV festival in 2008, Taylor Momsen displayed her new glam rock style, which reflected her taste in music and her rockstar aspirations. That year, she adopted a more neutral wardrobe, tossing out anything and everything that contained pink or florals. Her upgraded style featured tons of punk rock colors, such as gray, black, white, and red, which progressed into 2009.

Not everyone can say that they lived out their teenage dream of leading a rock band and starring in their own music videos — but Momsen certainly can. The year 2009 turned into one of the most defining periods of Momsen's life due to the formation of her band The Pretty Reckless, in which she acts as both lead singer and rhythm guitarist. To complement her new gig as a 16-year-old female rocker, the "My Medicine" singer upgraded her wardrobe once again by implementing what has now become her signature look: pearl blond hair and a smudged smokey eye. In 2009, her go-to looks involved a combination of heavy eye makeup, front bangs, a shag haircut, and grunge rock apparel.

In 2010, Taylor Momsen showcased her vampy new look while attending the Bon Jovi secret gig in Spain, complete with red-tipped stockings, a leather moto jacket, and waist-length super-long hair extensions. At this point, Momsen had added racy lingerie to her everyday wardrobe. Most of her performances featured lacy bralettes, garter belts, choker necklaces, and minidresses with corset bodices. The "Heaven Knows" artist inspired a great deal of outrage when she debuted her provocative, lingerie-inspired clothing choices — at the age of 17, no less.

The following years saw an escalation of her sexy vampire looks. However, when asked about her revealing stage 'fits, Momsen explained that her style comes from a place of self-expression and her love for rock and roll, rather than a need to rebel or separate herself from her past work as a child actor. "I've always said rock and roll represents freedom," Momsen told InLove Magazine. "Freedom from everyday life, freedom from restraints, freedom from suppression. It's where my imagination can thrive. It's how I express myself with no boundaries. Plus, loud guitars and drums are awesome." So, how did she come to develop this bold personal aesthetic? "I like fashion. I like dark colors. I like makeup. Being in the public eye forces you to figure out how to put it all together, I guess," she said to Interview Magazine in 2010.

Taylor Momsen eventually toned down her female Ozzy Osbourne vibe off-stage — a bat once landed on her dress mid-performance, if you didn't know — so her outfits at various public events were considerably less racy between 2013 and 2015. While attending the Helmut Lang show during the Spring 2014 Mercedes-Benz Fashion Week in September of 2013, the "Death by Rock and Roll" singer donned an all-black Helmut Lang ensemble with Dr. Martens Gilda Boots. She styled her icy pearl strands in loose waves and traded her usual black kohl for a coating of unconventional red eyeshadow underneath her bottom lid. Momsen has always loved designer fashion and we're not alone when we say that she would have made a stellar model with her height and runway looks.

However, performing with The Pretty Reckless is her true calling. Her distinctive voice and compelling stage presence remind us of another iconic female singer: Stevie Nicks. Momsen channeled Nicks' witchy and whimsical energy in 2014 during a performance in Nottingham, England, where she donned a sheer gold filigree cape, blond curls, and black leggings. Her Stevie Nicks phase was short-lived, but the photo will go down in history.

When asked by InLove Magazine about her everyday style, Taylor Monsen said, "I've always described it as how I'm feeling at the moment. It's really a hodgepodge of the palette I have to work with. My everyday style usually is relaxed, baggy, and comfortable." What she failed to mention, however, is that her casual, everyday wardrobe falls somewhere between '90s grunge and early 2000s indie sleaze. In a photo posted on December 14, 2021, the "25" artist was seen posing on the streets of New York City wearing an oversized leather jacket, gray sweatpants, and calf-length lace-up combat boots. Does it get any more grunge than that? She paired her relaxed ensemble with silver jewelry, slim sunnies, and her perpetually tousled tresses.

She gave fans another glimpse into her casual, off-duty rockstar look in another Instagram photo shared on June 16, 2022. In the mid-rehearsal bathroom selfie, Momsen took a snapshot of her ripped denim, studded belt, black zip-up hoodie, and a tangled jumble of silver chain necklaces. The Pretty Reckless musician knows how to rock edgy street style while keeping fans on their toes with her unique fashion choices, including her retro Italian film star sunglasses, pink iPhone pop socket, and prickly beanie hat. Momsen's multi-faceted outfits are never boring, that's for sure.

At this point, Taylor Momsen wears her signature smokey eye so often that we wonder if fans would even realize it's her without it. To be fair, the smudged kohl eyeliner and eyeshadow combo has become her trademark look, and she clearly intends to keep it that way. In a photo posted via Instagram on February 3, 2023, Momsen applied a sparkly silver eyeshadow over her kohl-rimmed eyes to match her bedazzled minidress, sleek leather jacket, and knee-high boots.

When she doesn't appear in full Pretty Reckless fashion, Momsen often reaches for black sunnies, rendering her virtually unrecognizable, which is a smart decision as far as disguises go. In an Instagram photo posted on April 14 this year, Momsen sports her jumbo sunglasses, along with an oversized faux leather jacket, platform boots, and what appears to be carmine corduroy pants. Note how the "Just Tonight" singer is so creative with her goth-rock color palette to the point that blood red is the closest she'll come to light spring attire — and it somehow works. It's that very creativity and attitude toward fashion, beauty, and lifestyle that makes Momsen a trendsetter within rock culture.