In May 1997, Carolyn Bessette-Kennedy and John F. Kennedy, Jr, visited Milan, Italy. When looking at photos of Carolyn in Italy, to me, she always looks so laid back and relaxed, not as stressed as she looked in New York City. Her mother’s family was originally from Messina, located in Italy, and I wonder if she felt at home there in some sense. (Though, as an Italian American, I must point out that Milan and Sicily are very different cultures!)
Carolyn wore this outfit on May 15th, and it stuck out to me because she so rarely wore prints. This outfit is simple, comfortable, and elegant, much like most of Carolyn’s looks. I would also go so far as to say this is one of the seemingly rare times where she looked more casual than John. Usually, it was the reverse when the two were out and about.
Let’s dive into the original items that she wore for this look. I’ll also cover how to recreate in an affordable way using products available today.
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The Carolyn Bessette-Kennedy in Milan Look Breakdown
Dress
Let’s start with what attracted me to this look in the first place–the dress! The dress was by the designer, Stephan Janson, a protégé of Yves Saint Laurent and a well-established designer in his own right. He shared that Carolyn told him while shopping on this trip that she preferred black and shades of brown.
Looking at the dress, this is a chocolate brown and white shift cut dress with a geometric pattern, similar to an old landline phone. The collar is a demure ruffle boat neck. The sleeves are a slight bell sleeve. The length hits right above the knee. To me, the fabric appears to be silk. The hem of the dress looks to be a flutter hem.
Sunglasses
The sunglasses appear to be Carolyn’s favorite Aldo sunnies from Selima Optique. The brand also sells a similar style that is dedicated to Carolyn, which are slightly more oversized than the Aldos. Sometimes I wonder how many pairs of the Aldos she had because she wore them so frequently. I feel like I’m always losing my sunglasses!
Bag
Carolyn Bessette-Kennedy carried her trusty black Hermès Birkin bag on this outing in Milan. Some have speculated that Carolyn specifically carried the Hermès Birkin 40, which is often described as the workhorse of Birkin bags.
Sandals
Her sandals were reportedly black Prada thong sandals. I couldn’t find the exact model but they appear to have a 1″-1.5″ platform.
Carolyn Bessette-Kennedy in Milan Look Reimagined
Above, when possible, I linked to the original items that Carolyn Bessette-Kennedy wore in Milan. However, the price points of these items make them pretty much unattainable for most people (this writer included). So, I recreated the look with more affordable options. This isn’t a replication so much as it is a modern reimagining from this writer’s perspective. These items can also, of course, be found secondhand for less.
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Sources
The below sources were used to help write this post along with my original thoughts.
