Gwen Stefani's Style Evolution Has Been A Wild Ride

Gwen Stefani's fearless approach to fashion is iconic. She's never been afraid to push boundaries, and her decades-long desire to express herself in unique ways hasn't gone unnoticed. The "Hollaback Girl' singer was the proud recipient of the Rock Style Award at the 2001 VH1 Fashion Awards, the Style Icon Award at 2014's People Magazine Awards, and the Fashion Icon Award winner at the 2019 E! People's Choice Awards, proving she's never gone out of style. 

Though most associate Stefani's fashion prowess with her early days in the spotlight as No Doubt's front-person, for the singer herself, it started much earlier. The "Used to Love You" hitmaker's fashion flair actually dates back to her childhood, as she told The Hollywood Reporter she grew up watching her great-grandmother, grandmother, and mom make clothes. That later became the catalyst for a dream to start her own clothing line — a dream she's since realized. The star told Glamour she's had plenty of other influences over the years as well, sharing, "Whether it's trying to impress my husband, meeting [her former stylist and now ALC designer] Andrea Lieberman, or going to seeing a Vivienne Westwood fashion show. Anything along that way that's pointed me into a new direction to evolve as style."

But while Stefani has worn the odd outdated trend, her style evolution has truly been a wild ride. One "The Voice" coach has never been afraid to fully embrace. Speaking to The Hollywood Reporter, she said, "By its nature, fashion is always progressing. You can't hold it in one place or stand still. I learned to be very open because you're always evolving; that's what fashion is, too."

When Gwen Stefani first entered the spotlight with No Doubt, she leaned into her feminine side with an edgy twist. For a performance at Los Angeles' The Roxy, she gave us Madonna "Like A Virgin"-era vibes in a white, lace edge crop top, paired with a white, knee-length, polka dot skirt over red and white heart shorts and a pink belt. But, even back then, Stefani knew how to put her own quirky spin on fashion. She added unexpected blue and white long, striped socks with orange bows and flat, navy shoes. During another No Doubt show that year at a California beach, she paired a blue and white striped bikini top with a high-waisted skater skirt, white socks, and quirky purple flats.

Stefani told Glamour she was still in school when No Doubt formed and would often spend class time thinking about her future stage outfits. "As soon as I knew we had a show, I'd be off to the fabric store," she recalled. The singer also spoke to E! News about her early foray into fashion, admitting, "I just was so naïve to the fashion industry and didn't know anything about it. I just was doing my own thing."

Gwen Stefani had an obvious passion for Hollywood glamor in the '90s, which she told The Hollywood Reporter stemmed from her love for old movies. Her passion for the throwback era peeked through during a 1996 Los Angeles performance, where she wore a nude, fur-look jacket with red lipstick that set off her bombshell platinum blond locks — though that isn't Stefani's natural hair color. She paired the bold jacket with a black-and-white striped top (similar stripes were huge in the '50s and '60s) but put her own spin on the classic aesthetic via her more modern and punky, shiny brown pants and chunky boots.

Her penchant for classic Hollywood was no more apparent than at the 1997 American Music Awards though. She wore a long, black dress with sheer mesh over her chest and an over-the-top feather boa. The look gave Marilyn Monroe in "The Seven Year Itch" vibes, which made sense considering Stefani told Teen Vogue she was inspired the late icon. Stefani wore similar hair and makeup to the vintage movie star too, including the red lipstick that became her staple. "I love red lipstick so much because it feels like such a classic but it's still so personal," she told Marie Claire. "My favourite thing to do is recreate looks from different decades, basically anything that's vintage and iconic," she added.

By 1998, Gwen Stefani was all about colorful hair that matched her clothes. She attended the MTV Video Music Awards in a fluffy bra top with rhinestone covered straps, a velvet skirt over pants, and platform flip flops. She also applied gems around her eyes, adopted the '90s super thin brow trend, and wore deep red lipstick. Stefani's outfit missed the mark and she told Vogue it was inspired by Judy Jetson of "The Jetsons." She'd dyed her bob haircut blue and gave Marie Claire more insight into her decision to wear space buns, explaining, "I was in a bit of a weird space personally." She also explained her tresses had become damaged from over styling. "The space buns were the only way to deal with it. I just wanted to help it grow out and that was the easiest way to do it," Stefani shared.

The rockstar also matched her hair to her clothes in a more sophisticated way in 1999 for the "Go" movie premiere. That time, she opted for a less zany look that consisted of a long, black coat over black pants, a white top, and chunky platforms. She'd cut her hair into a voluminous flippy bob (one of the hottest hairstyles of the time) and added dark blue and black streaks that matched her clothes. Stefani told Vogue she didn't have a stylist or makeup artist at the time, admitting, "I know that I was all over the place! So when I look back at what I wore, I see a lot of mess. That was just me making it up as I went."

By 2000, Gwen Stefani began branching out beyond No Doubt into solo artistry(she released the track "South Side" with Moby that year). Her outfits represented her ever-increasing stardom, as she dialed up the glitz. At the Radio Music Awards that year, she wore a white tank top with an exposed black bra straps and sparkles over her chest, paired with rhinestone and pinstripe pants. Stefani, who still rocked space buns, later told Vogue of her love for tank tops, "I pretty much only wore tank tops my whole life 'cause, I don't know why, I just think they look cool. I had to be a little bit tomboy with a little bit glamor."

The following year though, Stefani's style had a major upgrade when she began working with a stylist. At the 2001 Billboard Music Awards, she collaborated with Andrea Lieberman on her accessory heavy, sporty, triangle bra top, white jacket, and punky houndstooth pants look. Stefani, who started wearing her hair long and straight, elaborated to The Hollywood Reporter, "Andrea Lieberman, my first stylist and this super gifted New York girl who was so much cooler than me, exposed me to high fashion and designers. She took my ideas and my heart and just made it all that much better."

Gwen Stefani's fashion had taken a grungier, yet glamorous turn by 2002. While performing at Glastonbury music festival, Stefani adopted a similar aesthetic to her 2001 Billboard Music Awards outfit. She wore a black-and-white striped top with exposed red straps, plaid pants with zippers along the legs, and green suspender straps. To complete the look, she added high-top sneakers, a studded belt with a custom belt buckle, and a fabric wristband with full glam makeup. "When I was in No Doubt, I never thought of myself as sexy. Even in my 30s, I was a tomboy," she told InStyle of her lack of uber-feminine pieces.

The following year, Stefani married her first husband, Bush frontman Gavin Rossdale. Although she leaned into a more feminine aesthetic on her special day, in keeping with her quirky fashion taste, her wedding dress was outside-the-box. Though the gown appeared pretty traditional from the top, it faded into pink at the bottom. "I said I wanted it to be over the top, but not traditional — I wanted it to be everything," she told Elle U.K. (via The Cut).

Gwen Stefani released her first solo album, "Love.Angel.Music.Baby," in 2004 and overhauled her aesthetic to represent her new era. She leaned into fashion worn by the Japanese Harajuku subculture, with a focus on classic Lolita styles. She embraced feminine shapes, pastel shades, and lace, as demonstrated by her MTV Europe Music Awards look which included a corset, mini skirt, and plenty of bows. She also swapped the super straight hair and ponytails she'd rocked in the early 2000s to return to her feminine, vintage-inspired curls. She also sported the style during a 2004 "TRL" appearance, posing in a frilly, lower torso baring corset that matched her plaid jacket and shorts. The singer had entered a new makeup era too, as she swapped bright red lipstick for a deep pink shade. 

That same year, Stefani's years of fashion experience were put to good use as she launched her own clothing line, L.A.M.B. In 2005, she dropped the more accessible range, Harajuku Lovers: A Fatal Attraction to Cuteness. That said, Stefani's love for Harajuku fashion drew backlash and allegations of cultural appropriation.

Stefani later told Allure, "That was my Japanese influence and that was a culture that was so rich with tradition, yet so futuristic [with] so much attention to art and detail and discipline and it was fascinating to me." She added, "If [people are] going to criticize me for being a fan of something beautiful and sharing that, then I just think that doesn't feel right. I think it was a beautiful time of creativity..."

Gwen Stefani served iconic celebrity maternity fashion in 2006 after announcing she was expecting her first child. At the time, the star's look evolved past Harajuku aesthetics, as she returned to red lipstick and gravitated toward animal prints (a huge trend at the time). At the Grammys, she wore a one-shoulder maxi dress with an Aztec pattern strip above her growing middle. The ensemble was still in keeping with Stefani's confident fashion flair, as the brown material faded into a gradient green. The dress landed Stefani on multiple best dressed lists and ushered in another new fashion era for the soon-to-be mom.

Around seven months after giving birth, Stefani appeared at a L.A.M.B. event in a structured leopard-print coat. She pulled up the collar on the outwear and paired it with semi-sheer black tights, classic black heels, and a pompadour. She belted the coat to add structure, and the 'fit seemingly represented a more grown-up, sophisticated side of the star.

Two years later, Stefani became pregnant for the second time and opened up about the experience changed her life, which likely influenced her style. "There was nothing left in me. I had no ideas," she told The Hollywood Reporter of trying to balance motherhood, No Doubt, and her fashion line. "I had so much insecurity. I felt like — help!"

By 2010, Gwen Stefani was a mom-of-two andhad adopted a more toned down style. She demonstrated her more demure and sophisticated approach to fashion at that year's Met Gala when she wore a shimmery, champagne dress with sheer tulle over one side of her chest and shoulder. However, Stefani being Stefani, she kept things interesting via an exposed black bra. She also showed a new side to her style in all an black ensemble for the L.A.M.B. Fall 2010 Fashion Presentation. While her jacket and shorts combo with semi-sheer tights and calf-high boots could have been boring, she made the look fashion-forward by opting for a slightly shiny texture. Adding to the interest was the Old Hollywood vibe with her glam; complete with a signature bold red lip and vintage-inspired curls.

In 2014, Stefani spoke to Glamour about how her fashion stages had little to do with her age. "For me, fashion is not really about age as much as it is reflecting your personality. Your personality is what it is," she said. "I don't see that as I've grown and aged and matured in my life that I have much of a different personality, so I feel like there's definitely an evolution of style."

Following years of colorful outfits, Gwen Stefani wore more black in 2015. One of her more memorable looks from this era came when she walked the Grammys red carpet in a strapless, structured jumpsuit with a half-sheer embellished panel over her torso. She paired it with simple black pumps and made the rare decision to swap her signature red lipstick for a glossy, nude pink. The "Cool" singer also opted for a dark ensemble for the Gwen Stefani In Concert event, but incorporated multiple different finishes to reflect her creative approach to fashion. She wore high-waisted fishnets under a black top and jacket with exaggerated ruffles on her shoulders, cropped leather-look pants, and leopard-print heels. The star wore nude lipstick and had also been experimenting with her hair, as she'd cut her locks into a choppy bob and added dark blue and black dye (which may have been a nod to her late '90s 'do).

The move toward darker shades may have reflected a difficult time in her personal life. Stefani filed for divorce from Gavin Rossdale that year and has been open about how difficult she found their split. "When my family fell apart it was a catastrophe. How do you pick yourself up from that?" she told The Guardian.

Gwen Stefani started dating country singer Blake Shelton in late 2015 and his down-home, casual style seemingly influenced hers. This was best represented by what appeared to be a newfound love for camo print. In 2016, she was spotted leaving "The Late Show With Stephen Colbert" in fishnet stockings under slouchy pants with this pattern, yet she stayed true to her glam style via cut-out stilettos, a sheer mesh top over a black bra, and a structured, long black coat that demonstrated the blending of two worlds.

We also saw the star in more overtly feminine pieces during this time, as seen with her 2016 Billboard Music Awards gown. Her glamorous, embellished dress had crystals over a sheer illusion material, and Stefani opted for more neutral makeup for the event (which proved she's a celebrity who totally transforms without eyeliner). "The Voice" coach spoke to Vogue about her new style era, sharing, "Ever since I met my husband, that part of me has really come out in my fashion more than ever — the femininity that I didn't really embrace for a lot of years, just because of being in a band with all guys and being on stage."

By 2019, Gwen Stefani's Oklahoma lifestyle had seeped further into her fashion choices. She wore a red plaid shirt and pencil skirt with white, fringed cowboy-inspired boots (with a stiletto twist, of course) while at SiriusXM Studios. She also posed alongside Blake Shelton on Instagram wearing a green and blue western-inspired jacket, fishnets, a white cowboy hat, and hot pink boots. Stefani's glow-down was deemed one of the most dramatic in celebrity fashion history, and not everyone was convinced by her country style. "Trying wayyy too hard to be/look country ....sorry!" one Instagram user commented on her upload. "Please!! Dont lose yourself Gwen," another wrote.

Although one could argue one of the biggest red flags in Stefani and Shelton's relationship is the fact that her lifestyle and look changed when they started dating, the "Hollaback Girl" singer has made it clear her new aesthetic was authentic to her. She was awarded the Fashion Icon Award at the E! People's Choice Awards that year and told E! News, "It just proves that if you just are true to who you are and just follow your own passion that weird things can happen...I love fashion. It never gets old for me."

Behind the scenes, Stefani appeared to favor comfort over fashion (and who could blame her?). It seems her husband is on the same page. "Gwen and I have done so much traveling and touring and work the first half of our lives that now we're like, 'Hey, I'm good to put my sweatpants on at 6 p.m. and watch 'Ozark' eight times. That's our life now, and we love it," Shelton told People.

Gwen Stefani's new lifestyle collided with her old one in a major way at Audacy's Leading Ladies event in 2005, where she walked the red carpet in Oklahoma-inspired woodland print boots, baggy camo pants, and a matching jacket. But the singer hadn't lost her sparkle (literally). She added an unexpected finish via a sheer, sparkly top and seemingly doubled up on fishnets, which had been her go-to for years. Stefani rocked a similar aesthetic at Wango Tango music festival via a cropped, frilly, green jacket over a white top, which was tucked into her blue jeans with sparkly fringe over her thighs. She also sported embellished stiletto boots, creating a look that wouldn't be out of place at a country music event.

It seems this star's fashion will only continue to evolve as she does. And Stefani has no problem with that. "Fashion and makeup are such an extension of our personalities and who we are at the time and who we want to be," the style icon told Vogue. But whatever Stefani wants to be next, she'll never not be a style icon.