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Rihanna shined bright Monday night at the 2014 CFDA Awards, where the 26-year-old was named ‘Fashion Icon of the Year.’

The honor, which was presented by Vogue magazine Editor-in-Chief Anna Wintour, solidified the pop singer’s status as a fashion luminary.

Meanwhile, Wintour praised the pop star for her effortless head-to-toe looks and stunning ensembles.

“Rihanna speaks to her fans with her every look,” Wintour said. “And what she says to them — and I include all of us in that group — is that it’s fun to feel a little boyish one day and dress up like a dazzling diva the next. I think that’s what she was going for tonight,” she joked.

Wintour was referring to Rihanna’s grand entrance that evening wearing a glittering mesh gown that was sheer enough to leave little to the imagination. The dress was designed by Adam Selman, who made the gown out of 216,000 pieces of twinkling cut glass and embedded crystals.

Rihanna channeled famous jazz singer Josephine Baker for the look, which came complete with a matching cap and gloves along with a pale pink fur stole — collectively making it one of her boldest fashion looks yet.

“The point is to be audacious, even jaw-dropping or button-pushing — and yes, we know she enjoys pushing buttons — while remaining true to yourself,” Wintour said.

The CFDA Awards are an annual event that “recognizes the outstanding contributions made to American fashion by individuals from all areas of the industry and related arts, with awards being given for design excellence.”

The evening brought out some of fashion’s most influential leaders, designers and celebrities. Among the attendees was Solange Knowles, who made her first public appearance since the scandalous footage of her fighting Jay Z in an elevator was released.

The “Losing You” singer arrived at the awards with light make-up, big hair and a shimmering, metallic floor-length gown.

Activist Bethann Hardison was also honored for her efforts to help racially diversify the fashion industry.

Upon accepting her award, Rihanna credited fashion for always being her “defense mechanism.”

“I think fashion has been an outlet for me to express myself, to speak up, to say who I am and to be very loud about it at times,” she said. “And I just like to have fun with it.”

Rihanna’s key advice to being so fashion forward? Don’t follow rules.

“There are rules,” she said. “But rules are meant to be broken.”

Take a look at Rihanna’s style evolution in the slideshow above — and tell us: which was your favorite look?

Follow Lilly Workneh on Twitter @Lilly_Works