Estelle’s Style Evolution – 10 Memorable Looks

Grammy Award-winning songbird Estelle is among the most popular English soul singers to make it big internationally. However, she didn’t make it there alone. Thanks to support from John Legend, Kanye West and her fans across the globe, Estelle went from being named the Best Newcomer in England to carrying away a coveted Grammy Award in America just three years later.


The following is a look at the evolution of Estelle’s fashion sense from the early 00s to today!

  1. Estelle breaks out – Estelle’s first break-out singles, “1980” and “Free,” helped her win the MOBO Award for Best Newcomer in 2004. She stepped out in a green mini dress and you could clearly see this was her first appearance on the red carpet. The dress is tacky and looks cheap. She was desperately looking for her fashion style.


2. Estelle poses backstage in the awards room at the MOBO Awards 2005, the tenth anniversary of the annual music event. She wore a knee length beige dress this time, still not feeling it though for an award ceremony.

MOBO Awards 2005 - Awards Room

3. Estelle attends MOBO Awards at Wembley Arena on October 15, 2008 in London, England. She wore a black and grey floral bubble dress.


4. Grammy winner

Estelle didn’t become a household name in the States until “American Boy,” her 2008 collaboration with Kanye West. The song was nominated for Song of the Year and won Best Rap/Sung Collaboration at the 51st Annual Grammy Awards in 2009. She wore a one sleeve metallic mini dress. It was definitely memorable.


5. Singer Estelle arrives for the 2010 Victoria’s Secret Fashion Show looking fab. Her makeup was on point and her black blouse and gold sequined mini skirt were everything!!!


6. At the 2010 Ween Awards, the singer wore a black halter jumpsuit with a white clutch. What I love about the jumpsuit, though, is how it’s belted at the waist and it’s not too flowy. Gives it more of a formal look. Hot, Estelle!


7. Estelle was a vision of beauty at the 2013 Grammy awards. Her hair was in a retro updo and her dress chic. The long sleeved crop top and long mermaid skirt made for a playful look for the award ceremony.

LOS ANGELES, CA - FEBRUARY 10: Singer Estelle attends the 55th Annual GRAMMY Awards at STAPLES Center on February 10, 2013 in Los Angeles, California. (Photo by Steve Granitz/WireImage)

8. In 2014 was the Gabrielle’s Angel Foundation Hosts Angel Ball where Estelle wore a lovely fitting grey floral dress and matched it with a maroon clutch. The look is quite average, nothing too special to note.


9. Estelle shows off her curves on the red carpet at the 2015 Billboard Music Awards in a see through black gown. Although she looked uncomfortable with the look, she rocked it and looked like a superstar.

2015 Billboard Music Awards Arrivals

10. This year Estelle stepped out for the Black women in Hollywood Awards Luncheon looking like she has truly come into her skin. She looked amazing in a maroon fitting dress with colorful embellishments. She kept the accessories simple and her makeup and hair was on point!


Over the years, Estelle has gone through many changes, from short hair to long hair and fierce fashion looks.

Estelles fashion evolution is evident, and we cannot wait to see it on the 10th of July at the Ngong Racecourse where she will be performing at the Blankets and Wine.

Will you be there?? Share your plans below.


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