Carolyn Bessette Kennedy Style Challenge: A Maximalist's Journey to Minimalism (2026)

I recently embarked on an intriguing challenge: dressing like Carolyn Bessette Kennedy for an entire week. As a self-proclaimed maximalist, this endeavor was initially daunting, given my penchant for excessive jewelry, makeup, nail polish, and bold colors. However, the recent resurgence of interest in her minimalist style, coupled with the popularity of Ryan Murphy's "Love Story: John F. Kennedy Jr. & Carolyn Bessette," prompted me to reevaluate my approach to fashion.

What I discovered was a delightful surprise. By embracing minimalism, I inadvertently crafted a versatile capsule collection from my existing wardrobe. This experience taught me the importance of simplicity and creativity in fashion, allowing me to express myself without relying on constant purchases.

Here's a breakdown of my week-long experiment, showcasing how I recreated Carolyn's iconic looks using only my own possessions.

Day One: The Evening Elegance

I channeled one of Carolyn's most iconic evening ensembles, which she wore to the Whitney Museum of American Art gala in 1999. I started with a crisp white men's button-down shirt and transformed it into a daytime outfit. Paired with a long black silk skirt, reminiscent of her Yohji Yamamoto ensemble, the outfit exuded sophistication. For footwear, I opted for woven leather sandals, paying homage to her signature style.

Day Two: Structured Simplicity

On the second day, I embraced a structured and tailored look. I began with cream jeans and a black cotton button-up from Country Road. To complete the ensemble, I carried my trusty black tech tote from Ganni, adding a touch of practicality to the outfit.

Day Three: Denim Delight

Midweek, I leaned into my love for denim, a nod to Carolyn's well-documented affinity for Levi's. I donned the Ribcage Straight Ankle style, known for its stretch and comfort. Havaianas thongs, reminiscent of those iconic photos of her in New York City, provided both style and support for my arches.

Day Four: Subtle Flares

For the fourth day, I opted for black slacks with a subtle bootleg cut, mirroring Carolyn's preference for a subtle flare. I kept the top simple with a grey knit from Country Road, creating a polished yet understated look. However, I quickly ditched the headband, as my constant need for sunglasses or reading glasses made it impractical.

Day Five: Minimalist Chic

On the final day, I embraced simplicity at its finest. I wore a white T-shirt and a black skirt, which was actually the slip from the satin skirt I wore on Day One. This outfit proved to be incredibly comfortable. I completed the look with a raffia tote, similar to one Carolyn had been seen with, and my trusty thongs and sunglasses.

Reflection and Takeaway

This week-long experiment was not only fun but also incredibly insightful. It taught me the value of embracing minimalism and creativity in fashion. By utilizing what I already own, I discovered a new appreciation for simplicity and the power of self-expression without constant purchases. While I may not fully abandon my maximalist tendencies, I'm definitely embracing this minimalist streak for now.

This experience highlights the importance of reevaluating our wardrobes and exploring new styles. It's a reminder that sometimes, less is indeed more, and that creativity can thrive within the confines of a capsule collection.

Carolyn Bessette Kennedy Style Challenge: A Maximalist's Journey to Minimalism (2026)
Top Articles
Latest Posts
Recommended Articles
Article information

Author: Kerri Lueilwitz

Last Updated:

Views: 5769

Rating: 4.7 / 5 (67 voted)

Reviews: 90% of readers found this page helpful

Author information

Name: Kerri Lueilwitz

Birthday: 1992-10-31

Address: Suite 878 3699 Chantelle Roads, Colebury, NC 68599

Phone: +6111989609516

Job: Chief Farming Manager

Hobby: Mycology, Stone skipping, Dowsing, Whittling, Taxidermy, Sand art, Roller skating

Introduction: My name is Kerri Lueilwitz, I am a courageous, gentle, quaint, thankful, outstanding, brave, vast person who loves writing and wants to share my knowledge and understanding with you.