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Your Guide to Dressing Like Carolyn Bessette

alannafairey
alannafairey
Jul 03 2023

Your Guide to Dressing Like Carolyn Bessette


It’s been nearly 24 years since she passed away, but the enigmatic Carolyn Bessette is still widely considered a style muse today. Known for her ability to effortlessly combine simplicity and sophistication, Bessette’s fashion choices continue to inspire and captivate the next generation of fashionistas. Want to emulate the style of this original It Girl? I’ve created a comprehensive guide on how to shop like Carolyn Bessette.


Remember: while taking inspiration from Carolyn Bessette’s style, it’s essential to stay true to your own personal taste and adapt her looks to fit your individual style preferences.


Effortless Sophistication

Carolyn Bessette was the poster girl for rocking neutral tones such as black, white, beige, and gray during the nineties. She also favored clean lines and well-fitted clothing. Look for tailored blazers, fitted trousers, and pencil skirts. Choose clothing items that are structured and sophisticated.



Staple Investments

Carolyn was known for her timeless style and was arguably the original ‘quiet luxury’ influencer. Select classic pieces like white button-down blouses, high-waisted black trousers, and tailored coats, since these pieces will never go out of style. You can master Carolyn’s everyday look with a pair of blue Levi’s jeans, a black sleeveless shirt, and a Prada coat, which she had custom-made in three colors. To really capture Carolyn’s look, it is best to avoid trendy or overly embellished garments.



Little Black Dress

Whether she was attending state dinners at the White House or walking the streets of New York City, Carolyn’s ability to elevate the little black dress to new heights remains unmatched. One of the little black dress' greatest strengths is its adaptability, whether it be for formal events, professional settings, or casual outings. Carolyn’s go-to choices were Yohji Yamamoto, Prada, and Calvin Klein.



Minimal Accessories

Carolyn often opted for minimal accessories, letting her outfits speak for themselves. Her style will forever be associated with her love for turtle headbands, which she wore with oval-framed sunglasses. Choose delicate jewelry such as thin gold or silver necklaces, simple hoop earrings, and thin bracelets. Need inspiration? Think Mejuri or Jenny Bird, brands renowned for their minimalism. Avoid chunky or flashy accessories.



Less is More

Carolyn’s makeup mirrored her style in many ways: clean, simple, and fuss-free. Aim for a natural makeup look with a focus on flawless skin and understated shades. Keep your hair neatly styled, and consider a sleek, straight look or a sophisticated updo.



At the core of all of her iconic looks, Carolyn Bessette was effortless and confident. No matter how you choose to recreate one of Carolyn’s looks, remember to carry yourself with poise and confidence, as it can enhance any outfit you wear. Just as Carolyn Bessette did.