Since the 1990s, Gwen Stefani has held the title of style icon, transforming her look numerous times throughout her illustrious career as both a worldwide celebrity and creator behind L.A.M.B. Despite this, she hasn’t shied away from making bold sartorial decisions. However, these adventurous picks have occasionally resulted in missteps—moments when she revisited passé styles that did little to advance her aesthetic boundaries and rather anchored her firmly in past fashions. Given that she’s part of Generation X, it isn’t entirely unexpected for Stefani to experience occasional wardrobe mishaps; after all, her sense of fashion continues to evolve, presenting fresh opportunities for stylish success alongside potential pitfalls.
During the peak of her career with the band No Doubt, Stefani embraced the grunge persona before transitioning into her vibrant “HarajukuGirls” era. This was later succeeded by a less overtly bold but still striking look associated with her “The Voice.” Throughout these phases, she consistently challenged boundaries and frequently impressed audiences. Consequently, her appearance has always captivated us. To illustrate,
Stefani’s actual hair color isn’t platinum blonde; it’s surprisingly distinct from that.
. To take things up another notch,
Stefani has also chosen to wear wigs throughout the years, contributing to her frequently changing hair colors.
Despite her nearly flawless image, Stefani has some questionable moments stored away in the old archives that she probably regrets.
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Gwen Stefani’s flowery outfit at the 1997 Grammy Awards resembled curtains from the 1970s.
Given her knack for pushing boundaries in style, Gwen Stefani’s ensemble at the 1997 Grammy Awards came as quite a surprise. Designed by Dolce & Gabbana, one might have assumed that pairing Stefani with this renowned Italian fashion brand would result in brilliance, yet it didn’t pan out that way. She opted for a long pastel pink gown paired with an eye-catching, oversized butter-yellow floral jacket featuring entirely distinct patterns. This look resembled attire more suited to grandmothers from the seventies. Despite her usual prowess in executing bold outfits, even she struggled to salvage the dowdy nature of this particular getup.
Gwen Stefani’s Ensemble for the Rolling Stones Show was a Combination of Poor Choices
Although the boxy blazer trend made a comeback in the 2020s, it’s not surprising that this quintessentially ’90s aesthetic fell out of favor, particularly when we consider an ensemble worn by Gwen Stefani during a 1998 Rolling Stones performance. Her choice seems like she aimed to evoke earlier styles but ended up presenting more as a mishmash of ‘90s trends taken too far. She paired a gray blazer with wide-legged trousers, chunky black footwear, and Bantu knots—hairstyles originating from the Zulu people of South Africa, which were culturally appropriated here. This particular mix felt dissonant; the blazer appeared matronly and overly structured against the large, loose-fitting bottoms. Even the heavy-duty shoes failed to enhance the overall appearance.
The Combination of Tiered Skirts and Pantaloons Can Be Challenging for Everyone
Pulling off pants underneath a skirt has always been risky, and this combination hasn’t worked well for most people. Even during its peak in the ‘90s and early 2000s, it remained challenging. In 1998, at the MTV Video Music Awards, Stefani’s take on this trend highlighted exactly why such styling should remain part of history. Her outfit included a dark skirt worn over loose black trousers. Adding another layer typical of the era, she complemented these with a fluffy light-blue bra-top matching her dyed hair, along with chunky platforms. Although we must admit Stefani made quite an impact with this bold ensemble, the overall effect did not benefit her image and reinforced our desire never to see this fashion return.
In 2001, Gwen Stefani’s outfit was an overwhelming mix of everything that went wrong during the early years of the decade.
Gwen Stefani made quite an entrance at the 2001 VH1 Vogue Fashion Awards in New York City, stepping out in what can only be described as the most outrageous ensemble conceivable—complete with every trend that didn’t survive beyond Y2K. Her getup was brimming with layers of mesh fabric adorning both her upper and lower body, complemented by fishnet tights. The pièce de résistance? A herringbone-patterned blazer, which looks just as outdated as another retro style: chevron patterns. These designs deserve nothing less than being stored away for good. To complete this chaotic look, she paired high-waisted, flowing capri pants with bright red and white heels. Nope, thank you very much.
Gwen Stefani opts for a nautical-themed ensemble at the 2004 Grammy Awards.
In the 2000s, nautical fashion was everywhere, so it’s no shock that Gwen Stefani, the reigning queen of fashion, jumped on board when the trend was at its height. Nevertheless, her interpretation of this maritime theme at the Grammys in 2004 remains etched in memory—though perhaps more for all the wrong reasons.
Dressed in a monochrome ensemble, she transformed herself into a modern-day siren with high-waisted, wide-leg pants featuring numerous buttons adorning the midsection paired with a snug, frilled blouse. Although the contrasting materials from the billowy halter neck and sleek bottoms created an interesting visual appeal, it seems almost unimaginable today to picture her wearing such attire again.
Her mane of hair cascaded wildly over one shoulder, embodying a disheveled yet quintessentially ’00s aesthetic—and ultimately resulting in what could be considered one of Stefani’s least flattering red carpet moments.
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