Carolyn Bessette Kennedy’s Looks Are The Perfect Everyday Uniform, Here’s How To Recreate Them For Singapore

There’s been an influx in discourse about Carolyn Bessette Kennedy’s style since FX’s new series Love Story dropped, but this obsession with what the fashion darling wore in the ’90s isn’t new.

It is true that in 2026, the late Calvin Klein executive’s style has become another internet trend, but it is ironic that looking like her is turning into one, considering she is the poster child for timeless dressing—someone who often sported a neutral colour palette and classic silhouettes that wouldn’t look out of place on any street today.

Elizabeth Beller, author of Bessette Kennedy’s biography Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, explains that her style evolved from something more bohemian to take on “a more subdued, simple flavour” for a specific purpose: “Perhaps it was simply the changing tide in fashion, or Carolyn not wanting to give the press anything to write about, or her transformation into what she thought Mrs. John F Kennedy Jr. should look like—a woman Jackie approved of.” 

Her style is not just about wearing what flatters her; it also performs a function, using her widely coveted wardrobe of muted Yohji Yamamoto and Prada basics, well-fitting denim and loafers to shun public attention while looking the part as a member of the elusive Kennedy dynasty. She is, as Beller describes, “refined, discreet and correct”, someone who “always understood the assignment” when dressing for public events.

Despite using fashion to keep a low profile, her outfits are gaining unprecedented scrutiny, yet it is not surprising given that her looks are really the perfect uniform for the contemporary individual—polished yet practical enough to go about daily activities. The secret to her signature style, unlike that of other trends, is not shopping specific brands, pieces, prints, or cuts, but rather a deep understanding of what proportions, colours and materials look best on her and achieves her goal of fitting in, resulting in a rotation of clothing tempered by restraint and utilitarianism.

Below, Bessette Kennedy’s most stylish looks suitable for our sunny weather, and how you can wear them yourself.

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1. For the Office

One of CBK’s most famous outfits is a masterclass in dressing according to your proportions, resulting in a balanced and sleek look. While she wears a black long-sleeved top here, we reckon it’ll work just as well when swapped out with a full length white tee. A beige midi skirt plus a classic boot in supple leather—no statement buckles, no slouch, platform or lug soles—finish the look.

Skirt, $175, COS

From the sheen of the satin and the cut of the skirt to the flow of the material, this skirt from COS is a great alternative to replicate CBK’s look, while having enough allowance at the hem to accommodate the extra bulk boots add.

Skirt, $66, Mango

If it’s the same structured shape you’re looking for, Mango offers a similar-looking pencil skirt in a midi length, which will hide the opening of your boots to create an elongated and seamless silhouette.

Boots, $109, Charles & Keith

Boots are an underrated footwear option, especially on rainy days. Beyond emulating Bessette Kennedy’s style, they also pair well with your favourite pair of culottes or shorts. This knee-high pair has the same classic almond toe and low block heels to give you extra height without discomfort.

Headband Set, $30, Mango

The ’90s style icon is known to be minimal when it comes to accessories, but when she does reach for one, it’s usually her signature tortoiseshell headband. Both options in this set from Mango match well with the rest of this tone-on-tone look.

2. For the Weekend

Contrary to the monochromatic looks we often see online, Bessette Kennedy did wear colour. Here, she wore a printed dress with a leather tote and slingback heels, the perfect easy outfit for a brunch. The key here is to dress up a casual dress with a structured tote and a shoe that is more formal.

Dress, $772, Doen at Farfetch

For the same breezy feel, choose dresses that come in lighter colours and lightweight fabrics such as this sleeveless silk dress from Doen.

Dress, $66, Mango

From the fit-and-flare style to the floral print, this midi dress from Mango is a great alternative that looks just as good as Bessette Kennedy’s Chanel one.

Bag, $576, Osoi at Farfetch

Swap out bags with logos and clasps for ones with minimal adornments. Osoi offers options with the same clean lines and in generous sizes too, so you can keep your hands free while you’re out.

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3. For an Evening Event

Bessette-Kennedy was all about the basics with the occasional twist. At the Brite Night Whitney annual fundraising gala in 1999, she crossed the halves of a white shirt for an asymmetric look, then tucked it into a long black skirt paired with black sandals—a great example of how you can be well-dressed for a formal event without the need for a dress.

Shirt, $159, Massimo Dutti

A good white shirt will take you a long way, especially when it’s Bessette Kennedy’s look that you want. Not all of them are made equal—ones made of rayon and linen, for example, are too slouchy, and any extra embellishments (including logos) are decidedly anti-CBK. This shirt by Massimo Dutti is made of cotton poplin, a lightweight material that gives you that crisp, clean and structured look.

Shirt, $620, Rohe at Farfetch

Let this Rohe shirt do all the work. While this one is not a spitting image of the one Bessette Kennedy wore, the mismatched fastening and open collar achieves what makes her look here extra cool. The pale blue and pinstripes give this one a more casual feel.

Skirt, $185, Entire Studios at Farfetch

Bessette Kennedy’s high-contrast outfit may look simple, but the devil is in the details. The slim fit of her long skirt keeps her look streamlined, while the flare at the bottom adds interest. This skirt from Entire Studios has an asymmetric hem that will give you a similar look.

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4. For Running Errands

Her ultimate wardrobe staple? A pair of bootcut jeans, specifically the Levi’s 517 model. She was spotted wearing it on multiple occasions, with various coats when out and about with JFK Jr., but our favourite look was when she matched them with a black tank and strappy sandals to walk her dog. This stylish yet effortless and practical look is great for just about anything, from running errands to a casual hang out with friends.

Jeans, $340, Ganni at Farfetch

You’ll be hard pressed to find a pair of Levi’s 517s identical to CBK’s, but if it’s her slightly flared, high-rise and cropped look that you’re after, Ganni has a great pair.

Jeans, $95, Levi’s at Lazada

If you prefer more stretch in your denim, try Levi’s. We love that this pair is in a darker wash, making it versatile enough for work and play.

Sandals, $60, Charles & Keith

These sandals are minimal without being boring, and they’re in a tonal colourway just like Bessette Kennedy’s. While flats are a more comfortable option, having a go-to pair of heels can instantly elevate a casual pair of denim.

Sunglasses, $15, H&M

CBK loves tortoiseshell, and so do we. To protect your eyes from the sun, sport a pair of minimal oval-shaped sunglasses, a style often seen on Bessette Kennedy.