Brite Nite Whitney Party, 1999

On March 9, 1999 John and Carolyn attended "Brite Nite Whitney" at the Whitney, a benefit in aid of the Upper East Side museum. If you'd like to read an awkwardly funny account of the night, the NY Post has an old article up (John is mentioned).

John and Carolyn at the 'Brite Nite Whitney' fundraiser, March 9 1999

"Brite and beautiful black tie" was the dress code and Carolyn gave it her own twist by pairing a men's white dress shirt with a ruffled black skirt by Yohji Yamamoto. Her accessories were a bit bolder - patent strappy sandals and a gold-chain handbag, along with an emerald coloured ring and her wedding band. Makeup and hair was kept sleek and minimal, with Carolyn opting for a sheer lip instead of her usual bright red (Clinique's Black Honey is a good dupe, and Revlon's Fig Jam a less expensive alternative).

My favourite thing about this look has to be the ruffled skirt by Yohji. If I recall correctly, the blogger behind the now defunct Ultimate Carolyn had the same one. The gallery below has a bunch of HQ images where you can really see the detail of the skirt.

Outfit details

Despite it being a look you could still pull off today, this was arguably one of Carolyn's more trendier outfits. The casual top + evening skirt combo was very much a late nineties trend. Sharon Stone had kicked off the whole thing at the past Oscars by pairing a lilac Vera Wang evening skirt with her husband's button down from the Gap, and the April issue of Vogue had covergirls Maggie Rizer and Kate Moss in ball gowns and Calvin Klein tees. And you have to admit the little gold chain mail bag was a very nineties thing as well. What did you think of this look?

Gallery of really HQ images below:

More images at Remembering CBK

P.S. How cute were John and Carolyn at this event?!

Newman's Own George Awards Gala, 1999

What do you get when you throw together a cinema icon and a political lifestyle glossy? Why the Newman's Own/George Awards Gala of course.

Paul Newman, Joanne Woodward,
JFK Jr and Carolyn

On May 19 1999 Paul Newman and John hosted a gala for their respective companies, honouring philanthropic corporations in America. This event was the second annual gathering of Paul's food company "Newman's Own" and John's political magazine "George" ... oh and Carolyn tagged along!

Carolyn wore a ruffled Yohji Yamamoto jacket and pants, nude sandals and her black Comme des Garcons clutch.

I have to admit, I hated this outfit the first time I saw it. I just could not understand why Carolyn, with her refined style and preference for simple lines, would choose a ruffled coat of all things.

John and Carolyn at Newman's Own / George Awards, May 19 1999

But with a bit of time and a learned appreciation for Yohji Yamamoto's designs this has come to be one of my favourite looks on Carolyn! Yamamoto's brilliant craftmanship should be noted in this piece. He managed to beautifully fold ruffles on the front part of a jacket without it being overwhelming - and when have ruffles ever not been overwhelming?! Admittedly, I was never a big fan of this look but it has grown on me so much that its one of my favourite CBK outfits. Carolyn knew how to take risks without resorting to flashy trends, and always wore her looks with an intelligence that seems modern even today.

I've tried looking for runway pictures of this jacket but anything before 2000 is hard to find. It might even have been custom made for CBK. I'll update the post and let you know if I do find something! As always, click below the jump to see more pictures!

Rubin Amanpour Wedding in Italy, 1998

My cousin is getting married this weekend and fortunately, or unfortunately depending on how you see it, I get to be a bridesmaid! Thankfully, the dress isn't bubblegum pink and there aren't any bows (in plain sight) but sadly I don't think it can top this outfit Carolyn wore to a 1998 wedding in Italy. A close friend of John's, diplomat and journalist James Rubin wed anchorwoman Christiane Amanpour in Bracciano. The couple married in a low key wedding and invited some decidedly high profile guests.

Carolyn wore a black ruffled Yohji Yamamoto cocktail dress, patent black Manolo Blahnik heels and accessorize with a black leather envelope clutch. Jewellery was kept to a minimum (pearl earrings) and her hair was pulled back in a low chignon. These heels have got to be one of my favourite pairs of shoes on Carolyn. I love the straps on the back. They were probably Carolyn's favourite too seeing as how she wore them to more than one black tie event. 

The whole look was very classic and I still see women dress like this today. To me Carolyn looks more like Italian aristocracy than a fomer PR girl for Calvin Klein! And like always, she kept her makeup very simple and opted for just red lipstick and mascara. 

I don't know if I'd be bold enough to wear black at a wedding. These days guests always steer in favour of pastel colours ... would it be something you'd try? 

White House Correspondents Dinner, 1999

On Saturday, May 1 1999 John and Carolyn attended the annual White House Correspondents Dinner. Sean Penn was their guest and he, along with Carolyn and John, added some high wattage celebrity presence to the event.

Carolyn wore a beautiful Jean Paul Gaultier pantsuit and necklace and had her hair slicked into a ponytail. Makeup was minimal and she stuck to her tried and true red lipstick and a bit of liner.

This is one of my favourite CBK event outfits, although I find myself saying that a lot, because it is still so modern today. I even remember seeing a similar JPG pantsuit on the runways a few seasons ago but alas I can't find that specific collection.

Anyways, to see all of the pictures I've gathered from this event click the "Read More" link! And if you have any photos to add please let me know :)