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Dolce & Gabbana at the 1997 Grammys
Gwen Stefani’s band, No Doubt, made it to the 1997 Grammy Awards with their ska-pop album “Tragic Kingdom.” Stefani marked the occasion with a pink silky set from Dolce & Gabbana that featured a floor-length dress and matching duster, accented with her signature red lips and platinum hair. Another memorable detail? A glittering bindi, one of several that she often wore during this period.
It’s not just that the appropriative bindi is mega-cringe. This outfit misses the mark because it looks fussy and matronly — a strange choice for the famously glamorous Grammys. The heavy floral pattern almost looks like pajamas, definitely not awards show material. That might be because Stefani was still getting used to red carpets, since No Doubt was still in its ascendency. Stefani even admitted to being a little starstruck. “This is better than prom,” she told an ET reporter on the red carpet. “It feels like we’re at prom, but we’re way older now.” She would eventually get better at dressing like a mega-star, but the early looks were definitely hit or miss.
Blue fur at the 1998 VMAs
For the 1990 MTV Video Music Awards, Gwen Stefani wore a furry blue bikini top that perfectly matched the hue of her hair. She paired it with a black skirt-pant combo and some era-appropriate platform sandals. It’s bad enough that Stefani cherry picks her aesthetic from other cultures, but it’s especially problematic that she does so to signal edginess, as she does with the blue bantu-esque knots that seem intended to signal “punk.” But the outfit isn’t just bad in a symbolic sense. It’s also a serious eyesore.
It’s confusing that her hair color matches her clothing. It’s also not clear what’s happening with the stiff hem on her plastic-looking skirt, which is hovering around her knees like the ring around Neptune. Stefani looks like “The Jetsons” idea of a punk rocker — never a good sign if one is hoping to look chic. The one bright spot? Those towering sandals that are giving us major ’90s nostalgia.
Red gloves at the 2001 Grammys
Gwen Stefani was still balancing her girly impulses against her punk rock reputation in 2001 when she hit the Grammy red carpet in a red ’80s-inspired party dress. While the dress itself is pretty, there’s too much going on with this ensemble, which could be the punchline to the classic riddle: “What’s black, white, and red all over?”
The look featured an overabundance of accessories. The only detail worse than the sheer red gloves — too matchy with the dress — are the fishnet stockings peeking out from beneath the hem, lest we forget Stefani has edge. She accented the look with a white baguette book, introducing a new color and undercutting any sense of cohesion. Finally, Stefani looks stunning makeup-free, so it’s mystifying how she managed to look so severe here. The dark, thin brows and vampy red lipstick aren’t doing this pale pop star any favors.
A faux-hawk at the 2002 Grammys
In many ways, a semi-sheer leopard dress and major bouffant is peak Gwen Stefani style. The ensemble that the “Just A Girl” singer wore for the 2002 Grammy Awards displays some serious ’80s and punk influences. But while it might be on brand, it’s just not a particularly flattering look, even for someone as beautiful as Stefani.
First, the dress seems to be badly fitted, bunching in some places and baggy in others. The harsh band across the hips breaks up the vertical line of the dress, disrupting Stefani’s naturally lithe frame. Then, the ruffled skirt is just too busy when combined with the intense pattern. Leopard print might be timeless, but that doesn’t mean it goes with everything. Then, Stefani’s hair is a mystery unto itself. The high-volume style certainly evokes a mohawk, which is probably what the rocker intended, but it’s a little too “Coneheads”-coded to make the best dressed list.
Sheer black dress at the 2015 American Music Awards
Gwen Stefani hit the red carpet in a sultry sheer black dress, proving she was still an uber-hot pop star, even in her forties. Stefani had just begun enjoying a career renaissance, announcing both a new single and a steamy new romance with Blake Shelton. The sexy dress seemed intended to prove Stefani still had it, despite her recent divorce from Gavin Rossdale, and had all the makings of an unforgettable revenge dress moment. But this odd dress has more red flags than Stefani’s then-new relationship with Shelton.
The dress is bad, starting with the silhouette so bulky that it undercuts any sexy effect the sheer material might offer. The high collar floats strangely above the rest of the dress like a choker, breaking up Stefani’s vertical line. Finally, the color is a harsh contrast against Stefani’s pale skin and platinum blonde hair, and seems to age her. If she wanted to prove she was thriving, she should have chosen something a bit less gloomy.