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Music’s Most Fashionable Women

by Neph Basedow – August 27, 2009

Cheeky salutes music’s most trendsetting women…

Gwen Stefani

Earning the title of Music’s Most Fashionable Woman, Gwen Stefani dominates the fusion of fashion and music. As frontwoman for pop-punk outfit, No Doubt, and successful solo artist, Stefani has set herself apart from her contemporaries, thanks to her diverse and innovative personal style. When No Doubt hit the scene in the mid-1990s, Stefani introduced her punk rock-influenced sense of style, which often consisted of plaid pants, tanks and tummy shirts. But as Stefani ventured into her solo career, she became a fashion mogul – even starting her own fashion line, L.A.M.B., which has become a respected fashion staple in many high-end stores. She now mixes classic retro looks, like glamorous dresses, platinum hair and cherry red lipstick, or edgy rock looks, like short-shorts and ankle boots. She is known for her love of cutting-edge Japanese (“Harajuku”) fashion, which has inspired many looks in her L.A.M.B. collections. Stefani’s progressive looks inspire women all over the world. She undoubtedly deserves the title of Music’s Most Fashionable Woman.

Jenny Lewis

As frontwoman for the otherwise all-boy rock band, Rilo Kiley, Jenny Lewis holds her own in terms of rocking the stage, as well as her own style. The child-star turned musician (you might remember her from Troop Beverly Hills) is known for her offbeat sense of fashion. An innovator through and through, Lewis blends her natural girl-next-door look with a retro throwback, and often rocks short-shorts, hot pants and unitards while onstage with her band. When Lewis began her solo career (with the Watson Twins), she often opted for a Loretta Lynn inspired look, donning feminine vintage dresses. The petite songstress proves she can balance a style just as chic as her tunes.

Katy Perry

She may be the newest songstress to the bunch, but the pop vixen has already earned attention for her bold fashion ensembles. Pop’s newest “it” girl often incorporates audacious pieces onstage – remember the outrageous Manish Arora carousel bubble dress she wore to last year’s European Music Awards? Perry oozes confidence and femininity, choosing dresses over pants, and bright splashes of color over drab neutrals. She incorporates her fun, youthful personality into her sense of style, integrating jumpers, rompers and frilly skirts. Although she’s new to the scene, Perry has quickly become an overnight trendsetter – and we can’t wait to see what she wears next.

Karen O

The Yeah Yeah Yeahs’ frontwoman dominates live performances with her fierce onstage persona. Although she oozes ‘androgynous Brooklyn hipster’, this frontwoman is on the cutting-edge of rock and roll fashion. Karen O embraces 80’s style, including tattered tees, torn stockings and token red lipstick. She often enhances her personal style by painting her face with matching color palettes. Karen O’s edgy and confident looks regard her as a style icon for women in rock and roll.

Zooey Deschanel

Perhaps the most fashionably understated of the group, this actress/songstress is known for her corky yet natural beauty and style. Deschanel opts for classic and feminine looks, like vintage-inspired dresses and lace pieces. As 50% of the rock-folk outfit, She & Him (with M Ward), Deschanel pairs her indie music with indie looks, including ribbon headbands and ruffled dresses. The 500 Days of Summer star has been turning heads for her blockbuster hits, mounting music career and her effortless sense of style – she’s our favorite triple threat.

About the Author: Neph Basedow

Neph is a New York native, Austin transplant and self-admitted music fanatic. After obtaining her degree in government and music at the University of Texas at Austin, Neph relocated to Chicago and is now embracing the 'flair' of the Midwest and the magic of its local music scene. A musician since age 10 and an avid show-goer, she is passionate about all things music. She loves discovering and supporting local artists and enjoys frequenting the city's independent music venues. Think your music sounds good? Let our Cheeky Soundgood decide. Contact Neph at for inquiries and submissions.