Now toasting the 20-year mark, the annual ceremony honors inspiring, accomplished women from all spheres. Movie stars, heads of state, activists, rockers, media innovators, and sports icons took the stage. Some of the dazzling dames even claim more than one of these titles.
The red carpet sometimes felt like a reunion, as old friends made beelines for each other. This made for eye-popping visions, as when actress Kate Hudson, wearing moonlight-platinum Lanvin, hugged Glamour cover girl Fergie, a firecracker in a tight, crimson Zac Posen gown, slit to the thigh, and flame-edged Casadei pumps.
Both glittered with Cartier diamonds, from Hudson's bangle to Fergie's whopping platinum-set cocktail ring.
Poured into a simple yet slinky, black stretch wool L'Wren Scott dress, Julia Roberts caught up with Queen Rania of Jordan, who wore a sequined Halston column. Their conversation was down-to-earth, focused on their families.
Turning to the cameras, Roberts urged women "not to be afraid of 30, be less afraid of 40."
With designer Donatella Versace as an honoree, there was a lot of Versace love in the house. Hilary Swank, caging her curves in an Atelier Versace gown with a bronze mesh torso, called the brand her "good luck charm."
Donatella herself wore a nude goddess gown from her Spring 2011 collection, featuring micropleats and long fringe tiers on the skirt. She told StyleList the modern idea of glamour is "more subtle" than in the past, needing only key ingredients like "shiny hair and confidence!"
"Mad Men" star Elisabeth Moss went a kickier route, with a short, strapless, bright blue Reem Acra dress paired with contrasting yellow peep-toe heels.
She revealed to StyleList that when she wants to feel glamorous, "a great pair of heels and curling my hair does the trick." Give that girl a Hot Tools curling iron and she's ready to roll!
Designer Tory Burch, shimmering in a sequin-striped dress from her namesake line, has even simpler rules for feeling glamorous. "Get some sleep! And drink a lot of water," she said.
Burch custom-designed a plunging black gown for honoree and Olympic skier Lindsey Vonn. "I'm just hoping everything stays in," confessed Vonn.
Once the presenters and award recipients started rotating to the podium, they shared heartfelt words of appreciation and encouragement.
The hottest power pair was Oprah Winfrey and Roberts. Winfrey, wearing a strong-shouldered suit with a floral-motif blouse, introduced the "Eat Pray Love" actress by gushing, "Being around her makes you want to live your life at full volume, full blast."
High praise indeed from the "live your best life" guru!
Winfrey continued, "She once told me that her home and her family is the harbor of her life... More than wealth, more than awards, feeling that kind of harbor, feeling that kind of peace... is what really makes you a powerful woman."
Roberts accepted her award with one of her charmingly off-the-cuff speeches. Holding the swooping red statuette, she joked, "Is it a brooch? Or for the hair?... Have a few drinks, we'll figure it out."
She then offered a mix of advice: "Know when to say yes. Know when to say no. Don't tuck your hair like this [behind the ear], it never looks good."
Surprise guest Janet Jackson co-presented Versace's award and spoke movingly of their emotional connection through the loss of a brother.
"We were dressed in Versace [at Michael's funeral]," she said, "which means we were dressed in love."
Jackson walked the red carpet in a sleek black Versace gown topped with a black fur, her hair curved into a short, sharp bob, the better to set off her huge, swingy gold hoop earrings.
Rock progeny Kelly Osbourne, poised in a Matthew Williamson minidress, championed honoree Constance McMillen, the teenager who stood up for equal rights when she was not allowed to attend the prom with her girlfriend.
"As most of you know, I kinda know how to dance now," rasped Osbourne, referring to her "Dancing With the Stars" stint. "So, Constance, f--- the prom, 'cuz you get to dance with me tonight!"
The last standing ovation of the night was reserved for the Lifetime Achievement Award winner, Cher.
Her ensemble was relatively sedate, with a black leather jacket, a long black skirt, and fishnets -- not a feather in sight. Perhaps she's taking a glitz breather after filming "Burlesque"?
Her co-star and presenter, Stanley Tucci, quipped, "I got to be very well acquainted with her and I'm exhausted." He went on to quote a Cher-ism: "As Cher once said, until you're ready to look foolish, you never have the possibility of being great."
Taking the microphone, the straight-shooting star looked back at her early determination.
"Sixty years ago, two things happened to me: I tried to run away from home on my tricycle," she recalled. "And I went to see 'Cinderella' in Grauman's Chinese Theatre, and I decided that that's what I was going to do. I was gonna sing and dance and be an actress."
The current Vanity Fair cover woman voiced a forceful wish: "What I would want for everyone, and especially women, is that you don't take no for an answer, because no is just some bull---- word that someone made up."
You can learn more about the honorees at Glamour's Web site.
This year's charitable partnership will benefit recipients Dr. Hawa Abdi and her daughters, doctors Amina Mohamed and Deqo Mohamed. These Somali women run a massive refugee camp, the only shelter for thousands of women and children. As Julia Roberts says, know when to say yes.
For a recap of another star-studded Glamour event, read on!