Meeting The Press, 1996

In 1996 fresh from their honeymoon in Turkey John F Kennedy Jr. introduced his new wife to the press. The newly hyphenated Mrs. Carolyn Bessette-Kennedy stepped out from her NYC apartment and suddenly all eyes were on the newest inductee to the Kennedy family. 

For her first 'official appearance' Carolyn wore a long camel skirt, black sweater and her patent Prada bag and brown leather Prada boots. 

I loved this outfit for many reasons. First, because of the colour palette. I'm a simple girl, black and camel account for about 60 percent of my wardrobe, so I loved that Carolyn combined the two colours here. Second, her hair and makeup is flawless and although you can just see how uncomfortable she is facing all those cameras and lights (who wouldn't be) she is so quintessentially Carolyn. And lastly, the fact that this outfit is so timeless. Who doesn't see woman at work trying to embody this simple and streamlined look in the office? A sweater, skirt and boots combine to make a powerful first statement. 

As always, click the "Read More" link for all 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?