Good News + Bad News: Do Our Favorite Style Icons Still Impress?

There are so many women who influenced our style choices during the 80s and 90s. Selecting 6 mainstream ladies to consider was harder than you think. But I laid my heart on my sleeve and gave some tough love to those who used to inspire, and some mad love to those who continue to make my day. Do our favorite style icons still impress us? What do you think? Do they still inspire you, or have you moved on? Let us know.

The bad news:

Do Our Favorite Style Icons Still Impress Anna Wintour

Anna Wintour


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I have defended this woman since she took the helm at US Vogue back in the 80s and have admired her determination, poise and ability to get the job done. She’s always scored bonus points for being mysterious and not pandering to cameras. While I still admire her ability to basically run Conde Nast as Creative Director, I am also starting to feel uncomfortable, in an awkward kind of way. The Kardashian cover, her vague and pathetic defense of Melania’s potential inclusion, and her decision to replace several top editors at Conde’s publications who know their field inside and out with basically, well, kids who are marketers, makes me frustrated and annoyed. It looks desperate, not strategic or innovative.

There is a fine, yet important line between staying relevant and pandering to a crowd that doesn’t even buy the high-end merchandise your magazine(s)/site(s) seem to cover editorially. She can do better. She’s done better.

Do Our Favorite Style Icons Still Impress Gwyneth Paltrow

Gwyneth Paltrow

Oh, dear. Clearly her Oscar shows that some people think she is a fine actress. However, it doesn’t occur to me that her celebrity status gives her anymore insight into food, health or lifestyle than my aunt with good taste. Using celebrity to build a lifestyle brand based on the cost of expensive and headline-making ingredients is anything other than a snake oil-like ploy that’s insulting to educated potential readers. Acting is clearly her forte, so why doesn’t she embrace her talent if money isn’t an issue? Or find a charity or good cause to which she can devote her time? Gwyneth, the idea of “tastemaker” is passé. You’re smart, lovely and still land compelling roles. There’s no need for the rest of it.

Do Our Favorite Style Icons Still Impress Madonna


My feelings have nothing to do with the typical arguments about her wardrobe choice versus her age. What bothers me is that instead of focusing on new music or performance of any kind, she seems to WANT us to be focusing on her sartorial selections. Has she always used fashion as a way of expressing herself? Yes. But what’s different now is that there is no new and exciting music that accompanies a new and exciting wardrobe. Instead she’s copying the kids, both in terms of her music and her wardrobe. Be a leader! It’s why we loved you, or let the wave recede. You can do better. You’re Madonna!

The good news:

Do Our Favorite Style Icons Still Impress Oprah Winfrey


Admit it: She made you laugh, made you cry and well, made it okay for you to admit you could struggle with a pound or two (or 15). The icon was brutally honest about her struggle with her appearance, even revealing how at one point she needed to buy two dresses and have them sewn together for a red-carpet event. And her way to cope with all of it? She recruited experts who taught us (everyone who also struggled) how to better, dress better and well, be better. And nothing has changed. She’s still fabulous, strong and isn’t afraid to be vulnerable to help millions of her viewers. High five.

Do Our Favorite Style Icons Still Impress Cindy Crawford

Cindy Crawford

I love this woman. Perhaps it’s because she looks as though she feels at ease with herself. She reminds me of what used to be true about French women: Aging with the appearance of grace (although we all know that they are rigorous and somewhat fanatical about skincare). She isn’t living vicariously through her daughter (um, think about this Gigi’s mom), isn’t afraid to be photographed sans Photoshop, and is a very, very savvy businesswoman. She’s still queen. Read our interview with Cindy Crawford here!

Do Our Favorite Style Icons Still Impress Gillian Anderson

Gillian Anderson

The 90s are back and so are the X-files. I loved her back in the day. She played a smart, gorgeous woman whose first and foremost goal wasn’t to bag her partner by the third episode. And her “secret weapon” wasn’t her charm, but her brain. Off-screen, she was super cute and unafraid to show her more feline qualities. Well, not only has she maintained an exceptional career as an actress (BBC-lovers know what I mean) bur she looks beyond terrific. Still a powerhouse.

–Tamsin James

Photos: Anna Wintour,   |  Gwyneth Paltrow,  |  Madonna,  |  Oprah,  |  Cindy Crawford,  |  Gillian Anderson 

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