The event buzzed with inspirational stories, no-holds-barred opinions, confessions, and plenty of wicked laughter.
To mark the awards' 20th anniversary, Glamour opened the occasion to the public with the help of 92Y. (The ceremony itself is invite-only.) As editor-in-chief Cindi Leive said at the start of the conference, "[Women] need one another's insights to help fulfill our lives."
The Glamour team organized two panels of extraordinary women speakers, plus a special performance from the play "Love, Loss, and What I Wore."
Panelists ranged from media master Arianna Huffington to headline-making model Crystal Renn. All offered lessons they've learned in their work and personal lives.
One of the clearest lessons: Put Brooke Shields and Sherri Shepherd in a room together and you will laugh 'til you cry!
Most participants focused on broad-strokes emotional support, avoiding political agendas.
Read on as StyleList recaps the highlights of each conference segment.
Love Your Work Life
Who Was There: Bobbi Brown, founder of the namesake cosmetics company; Huffington; TV host and author Padma Lakshmi; candy entrepreneur Dylan Lauren; designer Anna Sui; moderated by "20/20" news correspondent Deborah Roberts.
Discussing: How do these high-powered women define success? How do they balance their professional and personal lives?
Highlights: Brown drilled straight to the emotional core of the definition of achievement: "What makes you happy," she said. "To me, that's what true success is."
She also firmly believes "there is no such thing as work/life balance. That does not exist. We do our best but it's never perfect."
Brown shared a story of a moment when both her husband and the designer Jean-Paul Gaultier wanted to go to dinner with her.
"They both had stripes on, very different kinds of stripes!" she laughed. "I remember saying to myself, Pick a door... I remember choosing [my husband] and I've always been happy to have made that choice."
Huffington agreed with the lipstick luminary, chiming in that rather than aiming for perfection, success is "more like making the right choices enough times." She also hopes that by demonstrating a healthier mode of success, women can influence men.
"We women can help men -- first the men in our lives and then men everywhere -- to approach work/life issues in a different way," she asserted.
Best Advice: Lakshmi encouraged women to look for all sorts of people to emulate, including men or women who may have a different background than your own. "You don't need to have somebody exactly like you to learn from their achievements or their failures," she advised.
Huffington called out the female tendency for self-criticism, which she dubs "the obnoxious roommate living in my head." She advocated for women to take a more balanced view.
"We need to learn to come to terms with it. In my case, it was through humor because I was unbelievably self-judgmental," she explained. "[We need to] evaluate ourselves but not judge ourselves."
Huffington also flogged her quest to end sleep deprivation. For one easy fix, avoid keeping a computer or PDA near your bed so that if you get up at night you're not tempted to check your email.
Love Your Body
Who Was There: Reality star Bethenny Frankel; models Renn and Paulina Porizkova; young activist Katherine Schwarzenegger; professor and author Dr. Ann Kearney-Cooke; moderated by nutritionist Keri Glassman.
Discussing: How is the definition of beauty changing? How can women pursue a healthy body image?
Highlights: In one breathtaking moment, Porizkova asked Renn to stand up alongside her to demonstrate their similar sizes and frames. "Here's Crystal, a plus-size model... This is a plus-size model in the year 2010," she said (although Renn is now thinner than she appeared on the cover of her memoir).
Pointing to her own body, which has nearly the same measurements as in her swimsuit heyday, Porizkova deadpanned, "This is an average-size model in 1980. Times have changed."
Renn spoke passionately about her old mental habits of negatively judging the bodies of women she passed on the street. "I was a bully," she confessed. She changed her perspective when she realized, "I'm passing judgment because I'm judging myself... And what type of hell is that to live in?"
The panel also discussed the results of a recent Glamour poll, which concluded that over 40 percent of women are unhappy with their bodies, a percentage that hasn't changed since 1984.
Most panelists thought that increasingly retouched images of women in the media contributed to a sense of falling short.
Schwarzenegger said young women should be prompted to think critically about such images. "It's a matter of showing girls what reality is, what real women look like," she believes.
Of course, as some magazines have experienced, even unretouched images can spark controversy. Kearney-Cook touched on neuroscience findings.
"When neurons fire together, they wire together," she claimed. "Meaning, when you are always criticizing yourself or talking negative about your body, you're sculpting your brain to feel bad about your body.
"Instead, we have to challenge ourselves and say, What are my signature strengths? Not [to think] that I have to have the best body to do the best with the body I have right now."
Best Advice: Renn asked women to share their opinions with magazines and designers. "When you see something you like, absolutely say so. If enough people do it, I really believe something can happen... You have power!" (Glamour magazine's own response to the public acclaim for a plus-size model who appeared in its September 2009 issue is living proof.)
When the inevitable topic of plastic surgery for young women came up, Porizkova burst out, "Don't! Please do not erase your character and who you are in favor of becoming like everybody else." She's equally outspoken about celebs who nip and tuck.
Porizkova believes people should wait until they are older to go under the knife. She acknowledged the temptation, though, admitting that if surgery had been an option when she was a teen, "I would have redone myself from top to toe... I would have looked Swedish, for one."
Schwarzenegger suggested listing your positive attributes whenever your inner critic pipes up. Renn backed her suggestion, challenging women to double the number of positive things for every negative thought.
Frankel exclaimed that it's particularly important for mothers not to say negative things about themselves around their children. At bottom, she said, "It's so self-involved to constantly think about what we look like."
Love, Loss, and What I Wore
Who Was There: Shields; Shepherd; actresses Jamie-Lynn Sigler and Natasha Lyonne; moderated by "What Not to Wear" style expert Stacy London.
Discussing: The emotional power of clothing, style aspirations, and cringe-worthy prom dresses.
Highlights: The actresses read excerpts from the play, then opened up during a warts-and-all Q&A with London.
Shields brought down the house by miming what it takes to remove Spanx, squirming and rolling an imaginary pair down her legs. "Sometimes you have to take them off before you leave the restaurant," she joked.
She also cited her children and her mother as her style inspirations because of their confidence. She confessed, "I would like to dress age-inappropriately... now that I finally look great."
After all, she does still fit into her original Calvins. Is that a hint for a Forever 21 gift card for the holidays?
Sigler spoke for many women when she admitted, "I like to think that every event I go to is a chance to redeem myself for what I wore to my prom." Although the dress wasn't too awful, she recalled, "I wore every hair trend at once."
Shepherd described her clothes as "memory keepers." "That's why I have a job!" cracked London.
Best Advice: Although London's known for her blunt wardrobe assessments, her core message was: "Before you love anything on your skin, you have to love the skin you're in."
Check out another debut inspired by Glamour's Women of the Year awards: nail polish!