Carolyn Bessette-Kennedy’s Jeans Guide

Where to find Carolyn Bessette-Kennedy's jeans today.

Much has been written and said about Carolyn Bessette-Kennedy’s style, and she’s a style icon I find myself returning to frequently. Objectively speaking, she embodies so many 90s trends including minimalism and classical style. But I’m here today to talk specifically about her denim and where to find similar styles and cuts today. So, let’s jump in and talk about Carolyn Bessette-Kennedy’s jeans!

I also post about Carolyn on my Instagram and have a dedicated Pinterest board if you’d like more CHD content on Carolyn. This post contains affiliate links, which means if you click on a link and make a purchase, I may receive a small commission. This post is also based mostly on my observations. I last updated the prices on March 20, 2024, so please note they may be outdated depending on when you are reading this.

Oddly, not too much has been written specifically about Carolyn’s specific denim choices. So, I have to go off history, my observations and the information out there as of now.

CBK Jeans 101: Cuts, Brands, Lengths, Washes, Rise, Distressing and Fabric Content

Carolyn Bessette-Kennedy's Jeans Denim Guide 101

Before jumping in to where similar styles can be found today, let’s talk about what types of jeans Carolyn actually wore. This section covers the basics of what to look for in hunting down Carolyn Bessette-Kennedy’s jeans. Whether it’s buying a brand new pair or finding a pair of vintage Levi’s or Rustlers while thrifting, CHD is here to help you achieve your fashion goals!


Since CBK rose to fame in the 1990s, this was pre-skinny jeans. In the 1980s, Carolyn did wear what we know as skinny jeans today, but they got dropped from the rotation once the 1990s hit. The styles she most favored in terms of jeans were boyfriend, flare and bootcut jeans. From time to time, she also wore cargo jeans and baggier, almost wide leg jeans.

Usually jeans were pretty polished but she sometimes wore pairs with some distressing and whiskers. I appreciate that it looks like she really wore her jeans, which makes sense given her career in public relations with the 90s king of denim, Calvin Klein.


I was able to track down that Carolyn favored Levi’s. Some have written that she specifically liked the popular 517 style. Given that she worked for Calvin Klein, we can also safely assume that she wore their jeans.


Carolyn went back and forth between ankle length jeans in the spring and summer and bootcut jeans in the fall and winter. In regards to just her jeans, I didn’t see any capris or cutoffs with a raw hem. I also didn’t see any super long cuts that became popular in y2k.


Carolyn stuck with medium and dark washes and avoided light washes. Any fading to the wash looks to be natural from wear. Some pairs may have subtle fading through the thighs. She also very rarely wore colored denim.


Most of Carolyn Bessette-Kennedy’s jeans were usually either mid-rise or high-rise. Most jeans of the 90s were high rise by default. Mid-rise jeans typically have a rise of 9″ in the front and high-rise jeans usually have 9.5″ or more. I haven’t seen any extreme high-rise styles on CBK, where the rise would be closer to 10″-12″.


When it came to wearing distressed jeans or not, Carolyn mixed in lightly distressed jeans with more polished looks. From what I can tell, it looks like the more casual distressed and patched jeans were saved for casual vacations in Hyannis Port while polished cuts were for the City. What I love most is that it looks like she actually wore her jeans by the whiskers at the hips.

Fabric Content

From what I can tell by looking at the images, it looks like most of the jeans Carolyn wore were close to 100% cotton. Most of the cuts held their shape as she walked and lived her daily live in New York. This leads me to believe they were probably more stiff than our modern jeans, which tend to have higher percentages of polyester, polyamide and spandex.

Adding more evidence, both Calvin Klein and Levi’s jeans of the 1990s were either 100% cotton or 98-99% cotton and mixed with a small amount of spandex. These fabric content would have added to the wear and whiskers seen on Carolyn’s jeans. Chances are that she didn’t wash them unnecessarily, which is what most denim experts recommend.

Carolyn Bessette-Kennedy Jean Rules

After taking in the basic 101’s of CBK’s preferred denim style, here’s a quick list of rules that you can follow to get her denim look. Of course, I always encourage people to have their own personal style, but if you are going for that Carolyn Bessette-Kennedy look for denim, here’s some rules to consider following.

Everything is polished, even when it’s not perfect. Carolyn picked jeans that wore in very naturally. Hemlines were always finished and the distressing and whiskering was minimal. When picking jeans, go for jeans with a clean look.

No raw or rolled hems. Carolyn went for finished hemlines, so avoid raw hemlines to get her style. Don’t roll them, even on vacation. In lieu of rolling jeans, opt for an ankle crop.

Avoid light washes. Instead, go for medium and dark wash denim. Lighter medium wash is OK for casual vacations.

Show off the waistline. Carolyn almost often tucked in her shirt, which shows off the waistline of the jeans.

Don’t go for an extreme high or extreme low waistline. She went for medium and high rise jeans. However, the high rises were on the low end of high. So, avoid extreme high rise. I also didn’t see any images of her in low rise jeans, which were not popular at the time.

Carolyn Bessette-Kennedy’s Jeans: Where to buy today

Now that we’ve established the basics of Carolyn Bessette-Kennedy’s jeans, let’s jump in and talk about where to find these styles today. CHD is a big proponent of shopping secondhand and thrifting. While the jeans mentioned in this section are new, similar styles can often be found at the thrift store.

Cropped Ankle Length Jeans with a Slight Flare

Carolyn Bessette-Kennedy's Jeans: Cropped with Slight Flare

Similar cropped and slightly flared jeans available to buy now:

  1. Madewell Kick Out Mid Rise Crop Jeans ($55.20)
  2. The Yaya Mid-Rise Crop Flare Jeans by Pilcro ($89.95)
  3. The Hustler Ankle by Mother ($159.60)
  4. Farrah High Waist Kick Flare Crop Jeans by AG ($94)

Bootcut and Straight Cut Jeans

Carolyn Bessette-Kennedy's Jeans: Bootcut Straight Jeans

Similar bootcut and straight cut jeans available today:

  1. Good ’90s high-rise straight-leg jeans by Good American ($96)
  2. Isabel Marant Étoile Belvira Bootcut Jeans ($161.72)
  3. Citizens of Humanity Vidia Mid-Rise Bootcut Jeans ($238)

Casual Boyfriend Jeans

Carolyn Bessette-Kennedy's Jeans: Casual Boyfriend

Similar casual boyfriend jeans available to buy today:

  1. Distressed Boyfriend Jeans by R13 ($495)
  2. Gap Mid Rise ’90s Loose Jeans with Washwell ($79)
  3. Dre Baggy Boyfriend Jeans by rag & bone ($135)

Thanks for reading!

I hope you loved this post. Carolyn Bessette-Kennedy is such a style icon, and I really enjoyed doing this deep dive on her denim choices.

Leave a Comment


  1. Claudia wrote:

    Hey, great article and very informative! Do you by any chance know who designed the jacket she wears in the photo you have up there of Carolyn with an ll bean boat and tote bag?

    Posted 3.26.24 Reply
    • Can't Hardly Dress wrote:

      It took some digging but I found the answer for you! I will make a standalone post now and comment again with the link because it turns out this is a common question on the internet!

      Posted 3.27.24 Reply
    • Can't Hardly Dress wrote:

      Hi CLaudia! I’m back and hope you see this. Here’s the post on what I was able to track down on this coat:

      Posted 3.27.24 Reply