
Carolyn Bessette-Kennedy’s vacation looks on Martha’s Vineyard are some of my most favorite looks of hers. Her style on the Vineyard was more casual than in New York City. This look is a good example of that–slouchy distressed boyfriend jeans with a patch a knee and a simple oversized white button down. Her hair is also tussled and wavy, likely from the humidity and ocean air. So, beach waves before beach waves were a thing. Along with the black varnish on her toe nails, I love this look so much.
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Slouchy boyfriend jeans with a white boatneck tee

Carolyn also wore these jeans on at least one other occasion on the Vineyard, paired with a long sleeve white long sleeve boatneck tee. This looks like a different occasion potentially since there is no toe nail polish in the image on the right. However, the image is a bit low quality, so I’m not entirely sure.
I love the broken in look that these jeans have, that tells me she likely wore these jeans a lot though these are the only photographs I’ve see of these jeans. It’s possible these jeans were originally sold in a distressed condition or Carolyn may have had someone distress them for her or done it herself. Working for Calvin Klein, it wouldn’t surprise me if she had access to denim customization services.
What style jeans were these?
OK, time to dive in to what jeans these likely were as well as what to look for when replicating this look. As a fashion reseller with 10 years of experience in women’s clothing, including vintage denim, I’ll be using both research and my own knowledge to hunt down what jeans these are!
Levi’s 517s
It is well documented that Carolyn was a big fan of Levi’s and often paired them with high end designer pieces. One of the cuts she wore were the 517’s, and this pair closely fits the bill of the 517s based on the cut.
History of the Levi’s 517s
Introduced originally as a men’s bootcut jean under the orange tab in 1969, the cut was very popular throughout the 1970s. I wasn’t able to track down when the women’s 517s were launched but here’s what makes women’s 517s…517s:
Let’s look at what makes 517’s:
- Subtle flare
- Mid-rise waist that sits at the hips
- Zipper fly
- Small bell leg opening
- Signature stitching on the back pockets featuring a “V” shape and two diagonal lines.
These Boyfriend jeans were likely Levi’s 517s

Given the characteristics of 90s Levi’s 517s, I’m fairly certain Carolyn was likely wearing 517s in these photos. I pulled up a pair of vintage 1990s 517s from Etsy and compared them to the ones Carolyn was wearing. In addition to these similarities, the jeans also have the signature 517 bell flare and mid rise.
Here’s the similarities between the two that I see to confirm these are Levi’s:
- Button looks very similar
- Belt loop placement is the same
- Orange stitching present in both images
- Stitching around the zipper is similar
- Same rivet placement

Taking a look at the same Etsy listing of the vintage 90s 517s, they certainly look very similar to Carolyn’s.
Was the Distressing Original to the jeans?

Whether the distressing on her jeans was original to them, I’m not certain. Distressing certainly existed in the 90s but didn’t gain popularity until the early 2000s. That being said, there is one clue that makes me think Carolyn possibly bought the jeans with the distressing and patch.
Carolyn was 5’9″, well over the average height for American women. There are some suggestions out there that the ideal jean inseam (that’s the measurement from the crotch seam to leg opening) for a 5’9″ woman is 34″. In my research of women’s 517s on Etsy, inseams likely ranged from 25″-32″. Back in the 90s, it wasn’t as common to have short and tall sizes, though if anyone had access to it, it was Carolyn.
All that being said, I want to point of the patch placement on the knee. Typically, patches will hit at the knee but here the patch is above the knee slightly. The jeans also appear as cropped. However, my guess is these aren’t meant to be a cropped style, and rather our very tall Carolyn is wearing a pair with a shorter inseam versus a pair that’s deliberately cropped for her height.
That being said, this is just a guess based on images I have available along with resources on the 517s and my own knowledge.
Get the vacation boyfriend jean look
Now that we’ve gone over what style Carolyn was likely wearing, I’ll share some similar styles. The 517s are still available by Levi’s and the vintage market is going strong. So, if you’re looking for a vintage pair of 90s Levi’s 517s, eBay or Etsy are going to be your best bet. I’m not going to be linking to these marketplaces, because usually these are one off pairs that are gone once purchased.
Sources
These sources were used to help inform this post.









