Sign in to wowOwow

Enter the email address that you used when registering at wowOwow.
The password field is case sensitive. Click here if you have forgotten your password.

Please register for wowOwow

Newsletter subscriptions
Sign up to receive wowOwow's weekly newsletter and get our best picks delivered right to your inbox. Our newsletter content is hand-picked by the wowOwow editorial team and provides the top features, news, and commentary from our site. Subscribing to our newsletter is free and safe. We will never share your email or other information with a third-party without your direct consent.
By registering, you indicate that you have read and agree
with our privacy policy and terms of service.
Home › Style

Style | 12/29/2008 9:15 am

wOw Presents: The 15 Over-40 Female Fashion Leaders of 2008 (Photos)

Photo Essay

Play Slideshow
Michelle Obama
Welcome to the First Annual Over-40 wowOwow Best Dressed List!

You may disagree with who is on it, but perhaps you will agree, at least philosophically, with our deciding factors: women in the public eye who support the international fashion industry, who dress age appropriate but who nonetheless take calculated risks, who wear trends but are never victim to them, and most essential of all, they are women who are comfortable in their own skin because, when you are, you can wear anything from sackcloth to silk and make it look good.

Click on through to see who’s made the cut!
Read more about: Anna Wintour, Barbara Walters, Carla Bruni-Sarkozy, Carolina Herrera, Chanel, Daphne Guinness, Diane von Furstenberg, Elle Macpherson, Gucci, Halle Berry, Iman, Kelly Klein, Lee Radziwill, Madonna, Michelle Obama, Sarah Jessica Parker, Vera Wang

29 Reader Comments (so far…) Sign In or Register to comment

Ann Coulter Crazy, Souless, Evil B*tch
Lily, Couldn’t have said it better. I greatly prefer clean-cut, simple and fresh…so I like Michelle’s look most of all…am turned off by overdone ‘look at me’ clothes. Liz Smith always looks classy with a distinct style that suits her. Jackie was the best because her look was simple elegance. Am looking forward to Michelle’s clothes and hope she keeps it uncluttered and youthful. My first trip through college was in design school….so like you, appreciate quality design that whispers, as opposed to screaming.
By Ann Coulter Crazy, Souless, Evil B*tch on 12/29/2008 2:15 pm
Susan B
Madonna looks like a bunch of dillweed on steroids. Interesting, yes. Foolish, absolutely.
By Susan B on 12/29/2008 2:34 pm
Ann Coulter Crazy, Souless, Evil B*tch
Susan, I thought she looked outfitted for a remake of The Flintstones. Maybe designers purposely make their clients look outlandish for the press….then they can knock-off the orginals at lower price points for Madonna wannabees and scoop up the dough.
By Ann Coulter Crazy, Souless, Evil B*tch on 12/29/2008 3:42 pm
Susan B
… or a remake of the Creature from the Black Lagoon. I think you’re right about pushing the outlandish, but as terrific as her body is, she can no longer get away with these kinds of costumes. She does look foolish. Maybe she doesn’t care. It’s her rep.
By Susan B on 12/29/2008 5:00 pm
elaine s
Lee Radziwill looks great. Michelle Obama looks good and I hope she will continue to choose very simple, clean lines - much like Jacqueline Kennedy.
By elaine s on 12/29/2008 3:51 pm
Irish Eyes NY
elaine s: Yup, but I hope Michelle finds herself a designer that will fit her personality and needs. She could certainly do better than she is doing now. The dress on election night was a nightmare. I
By Irish Eyes NY on 12/31/2008 7:10 pm
larry ward
I agree!! Larry ward
By larry ward on 01/01/2009 3:32 pm
Sandbee (FB) 54
I thought maybe someone left Madonna in the fridge too long, I have a few things that look sort of like that when I throw them away.
By Sandbee (FB) 54 on 12/29/2008 4:20 pm
Irish Eyes NY
I agree sandbee: Madonna looks horrible. My opinion of her is very low anyway, I consider her nothing but a tramp.
By Irish Eyes NY on 12/31/2008 7:12 pm
Diana T
Madonna really looks out of place on this series of pics. She is an icon of What Fashion Isn’t. As for Vera Wang, well, time for a make-over, Vera…you have too many good features being hidden by outdated hair and clothes that hide everything.
By Diana T on 12/29/2008 6:01 pm
Buh- Bye
Is Madonna wearing Astroturf?
By Buh- Bye on 12/29/2008 9:26 pm
Frannie Em
PI LOL
By Frannie Em on 12/30/2008 2:44 am
Frannie Em
I know Madonna is now of the horsey set, but isn’t she carrying it a bit far by wearing her horses’ alfalfa? I have to agree with Carmel, when I first saw it I thought of Betty Rubble and Wilma Flintstone.
By Frannie Em on 12/30/2008 2:52 am
Buh- Bye
I have to say, I love her for wearing it, anyway.
By Buh- Bye on 01/04/2009 10:43 am
Chrome Toe
okay… i don’t like what Madonna is wearing in this particular photo but agree with her on the list. and agree with all of the women on this list with the exception of the actual designers like Vera Wang, Caroline Herrera and Kelly Klein. they all have a product to sell and a look that is stale in my opinion. Diane Von Furstenburg (or however it’s spelled) can look fresh but still looks like an advertisement a lot of the time. Lily… i love Barbara Walters in that dress! i think it looks amazing on her. Carla Bruni always looks great. she dresses her age without looking matronly. just enough of a fresh edge to be a musician while still approprite enough to be the first lady of France. But then you’re all saying.. “but she’s wearing pink chaps!” right? lol!!!
By Chrome Toe on 12/29/2008 10:01 pm
12next ›last »