11 Sleek Style Essentials to Channel Your Inner Carolyn Bessette Kennedy

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11 Sleek Style Essentials to Channel Your Inner Carolyn Bessette Kennedy

American love story: quality basics.

Carolyn Bessette Kennedy wearing sunglasses and a headbandCarolyn Bessette Kennedy wearing sunglasses and a headband

Getty Images

Key Takeaways

  • Carolyn Bessette Kennedy’s classic style, which highlights lots of quality basics, is all the rage right now.
  • We found 11 of her wardrobe essentials that you can still shop today.

I don’t believe in capsule wardrobes, unless that capsule came straight from the mind of Carolyn Bessette Kennedy.

If I was shopping at Calvin Klein in 1990 and forced to choose between everything I own and 10 things the sales-associate-turned-publicity director fully approved of… it would be a hard choice, because I do like my things. Still, those 10 items would likely be all I’d ever need. I’d be a fool not to go for them.

As we obsess over a fictionalized version of CBK’s style every week on American Love Story, it’s nice to remember that many of the ’90s style muse’s favorite pieces still exist, whether in the exact format she found them in or new iterations. Even more excitingly: It’s so easy to work them into your own wardrobe. You don’t have to throw anything you own away, but maybe you’ll end up wanting to? One of the privileges of finding the perfect jeans or white button up or sunglasses is that you no longer need to shop around.

Keep reading to discover 11 (like I said, 10 is tricky!) CBK style essentials.

The Sunglasses: Selima Boutique Aldo Glasses

Selima Optique Aldo SunglassesSelima Optique Aldo Sunglasses

Selima Optique

$520 at Selimaoptique.com

Let’s start off strong with the exact sunglasses our muse held dear (and wore with every outfit). Selima Optique’s Aldo sunglasses (“the frame of choice of the ‘ultimate beautiful person’ as she was voted by her high school classmates,” they explain on their website) are available in four colorways. You can also get a slightly larger version called The Carolyn, or an even bigger pair named CBK depending on your personal eyewear size preferences.

The Headband: C.O. Bigelow Wide Tortoiseshell

C.O. Bigelow Wide HeadbandC.O. Bigelow Wide Headband

C.O. Bigelow

$40 at Bigelowchemists.com

Another exact match from early ’90s NYC: the headbands stocked at the famed C.O. Bigelow drugstore in Greenwich Village. The paparazzi spotted Bessette with her lemon blonde hair pulled back by one of these classic silhouettes more than a few times.

A Crisp White Shirt: Alex Mill Jo Shirt in Cotton Poplin

Alex Mill Jo ShirtAlex Mill Jo Shirt

Alex Mill

$145 at Alexmill.com

Oh, those tailored shirts. This is the sort of wardrobe essential that you might need to try a few options/sizes of—your perfect white button up might be different than someone else’s! But Alex Mill’s “100% crisp-to-the-touch cotton” selection is a perfect place to start. (It even has a little pencil pocket, which is incredibly chic.)

A Boxy Black Tote: Reformation Beatrice Tote Bag

Reformation Beatrice Tote BagReformation Beatrice Tote Bag
$548 at Reformation

Alongside her Birkin, CBK was often seen slinging Prada’s boxy Spazzolato tote over her shoulder. You can find them on resale sites, and fingers crossed another re-edition (they released one in 2022, and that was long before all this madness) is on its way. Otherwise, you could try a similarly boxy black bag! Reformation’s Beatrice has a great rectangular shape with the teeniest bit of slouch.

A Statement Jacket: Nour Hammour Althea Coat

Nour Hammour Althea CoatNour Hammour Althea Coat

Nour Hammour 

$3,200 at Nour-hammour.com

Truthfully, I could choose 10 jackets alone from CBK’s collection. She was so good about a coat, wearing options that ranged from delightfully oversized to fitted and belted, and sometimes even featuring a (rare) pop of color or print. This lengthy pony hair number from Parisian ready-to-wear brand Nour Hammour would feel right at home in the collection.

A Pair of Bootcut Jeans: Levi’s Wedgie

Levi's Wedgie Bootcut JeansLevi's Wedgie Bootcut Jeans

Levi’s

$110 at Levi.com

Bessette was a fan of Levi’s 517 bootcut jeans, a chic style introduced in the ’60s that is still sold in men’s sizing. Though the name is far less chic, the Wedgie jean is the modernized women’s bootcut style from the legacy brand. These are made with 1% lycra for a little stretch, so if you want 100% cotton, go for the 517.

A Practical and Chic Heel: Manolo Blahnik Carolyne

Manolo Blahnik Carolyne HeelManolo Blahnik Carolyne Heel

Manolo Blahnik

$995 at Manoloblahnik.com

Though these shoes were named after another famous Carolyn(e), socialite and designer Carolyne Roehm, Bessette helped put the almond-toed slingback on the map. It’s arrived in a thousand colors and finishes over the years, but black will always be classic.

And while you’re at it, you might as well add another pair to the collection. CBK also loved the brand’s Callasli slingback sandals, which remain just as popular today (Hailey Bieber wore them to celebrate her 29th birthday just this fall).

A Black Dress: L’Agence Akiya Satin Maxi Dress

L'AGENCE Akiya Maxi DressL'AGENCE Akiya Maxi Dress

L’AGENCE

$395 at Lagence.com

Now for the perfect black dress, or three. With plenty of events to attend, a gown was a regular necessity for this woman. Somehow, each and every one she wore was so classic I wouldn’t be surprised to see a version of it on store shelves today. This pretty option from L’Agence reminds me of a black silk slip skirt the publicist wore once upon a time, and I think she’d be pleased with the simple scoop neckline as well.

The Long-Sleeved Shirt: Petite Bateau Long Sleeve Crew Neck Tee

Navy long-sleeve TshirtNavy long-sleeve Tshirt

Petite Bateau

$60 at Petitbateau.us

Another staple: simple, high-quality tees—Carolyn liked these from Petit Bateau, which you can still shop today. You’ll need a long-sleeve, a short-sleeve, and a tank-top (again, look for that that scoop neck). Pick up each in navy and white.

A Pair of Tall Boots: Vagabond Leather Tall Boots

Vagabond Leather Tall BootsVagabond Leather Tall Boots

Vagabond

$240 at Vagabond.com

Alongside the heels, Bessette could often be seen wearing a pair of perfectly worn-in tall leather boots. The brown buckled Prada pair she owned was extra special, and these similarly square-toed Vagabond boots remind me a bit of them.

A Bandana: Free People Graceland Solid Hair Scarf

Free People Graceland Hair ScarfFree People Graceland Hair Scarf

Free People

$24 at Freepeople.com

And then there’s the honeymoon bandana. Soft blue and easy as can be to throw in your hair, it’ll look cool with your sunnies, your gown a la Renate Reinsve at the European Film Awards, or your bootcut jeans. Or maybe you can wear it just to keep the tears out of your eyes while you cry watching American Love Story or reading What Remains? I don’t know. There are options here.

Read more:

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If you click on links we provide, we may receive compensation.

11 Sleek Style Essentials to Channel Your Inner Carolyn Bessette Kennedy

American love story: quality basics.

Carolyn Bessette Kennedy wearing sunglasses and a headbandCarolyn Bessette Kennedy wearing sunglasses and a headband

Getty Images

Key Takeaways

  • Carolyn Bessette Kennedy’s classic style, which highlights lots of quality basics, is all the rage right now.
  • We found 11 of her wardrobe essentials that you can still shop today.

I don’t believe in capsule wardrobes, unless that capsule came straight from the mind of Carolyn Bessette Kennedy.

If I was shopping at Calvin Klein in 1990 and forced to choose between everything I own and 10 things the sales-associate-turned-publicity director fully approved of… it would be a hard choice, because I do like my things. Still, those 10 items would likely be all I’d ever need. I’d be a fool not to go for them.

As we obsess over a fictionalized version of CBK’s style every week on American Love Story, it’s nice to remember that many of the ’90s style muse’s favorite pieces still exist, whether in the exact format she found them in or new iterations. Even more excitingly: It’s so easy to work them into your own wardrobe. You don’t have to throw anything you own away, but maybe you’ll end up wanting to? One of the privileges of finding the perfect jeans or white button up or sunglasses is that you no longer need to shop around.

Keep reading to discover 11 (like I said, 10 is tricky!) CBK style essentials.

The Sunglasses: Selima Boutique Aldo Glasses

Selima Optique Aldo SunglassesSelima Optique Aldo Sunglasses

Selima Optique

$520 at Selimaoptique.com

Let’s start off strong with the exact sunglasses our muse held dear (and wore with every outfit). Selima Optique’s Aldo sunglasses (“the frame of choice of the ‘ultimate beautiful person’ as she was voted by her high school classmates,” they explain on their website) are available in four colorways. You can also get a slightly larger version called The Carolyn, or an even bigger pair named CBK depending on your personal eyewear size preferences.

The Headband: C.O. Bigelow Wide Tortoiseshell

C.O. Bigelow Wide HeadbandC.O. Bigelow Wide Headband

C.O. Bigelow

$40 at Bigelowchemists.com

Another exact match from early ’90s NYC: the headbands stocked at the famed C.O. Bigelow drugstore in Greenwich Village. The paparazzi spotted Bessette with her lemon blonde hair pulled back by one of these classic silhouettes more than a few times.

A Crisp White Shirt: Alex Mill Jo Shirt in Cotton Poplin

Alex Mill Jo ShirtAlex Mill Jo Shirt

Alex Mill

$145 at Alexmill.com

Oh, those tailored shirts. This is the sort of wardrobe essential that you might need to try a few options/sizes of—your perfect white button up might be different than someone else’s! But Alex Mill’s “100% crisp-to-the-touch cotton” selection is a perfect place to start. (It even has a little pencil pocket, which is incredibly chic.)

A Boxy Black Tote: Reformation Beatrice Tote Bag

Reformation Beatrice Tote BagReformation Beatrice Tote Bag
$548 at Reformation

Alongside her Birkin, CBK was often seen slinging Prada’s boxy Spazzolato tote over her shoulder. You can find them on resale sites, and fingers crossed another re-edition (they released one in 2022, and that was long before all this madness) is on its way. Otherwise, you could try a similarly boxy black bag! Reformation’s Beatrice has a great rectangular shape with the teeniest bit of slouch.

A Statement Jacket: Nour Hammour Althea Coat

Nour Hammour Althea CoatNour Hammour Althea Coat

Nour Hammour 

$3,200 at Nour-hammour.com

Truthfully, I could choose 10 jackets alone from CBK’s collection. She was so good about a coat, wearing options that ranged from delightfully oversized to fitted and belted, and sometimes even featuring a (rare) pop of color or print. This lengthy pony hair number from Parisian ready-to-wear brand Nour Hammour would feel right at home in the collection.

A Pair of Bootcut Jeans: Levi’s Wedgie

Levi's Wedgie Bootcut JeansLevi's Wedgie Bootcut Jeans

Levi’s

$110 at Levi.com

Bessette was a fan of Levi’s 517 bootcut jeans, a chic style introduced in the ’60s that is still sold in men’s sizing. Though the name is far less chic, the Wedgie jean is the modernized women’s bootcut style from the legacy brand. These are made with 1% lycra for a little stretch, so if you want 100% cotton, go for the 517.

A Practical and Chic Heel: Manolo Blahnik Carolyne

Manolo Blahnik Carolyne HeelManolo Blahnik Carolyne Heel

Manolo Blahnik

$995 at Manoloblahnik.com

Though these shoes were named after another famous Carolyn(e), socialite and designer Carolyne Roehm, Bessette helped put the almond-toed slingback on the map. It’s arrived in a thousand colors and finishes over the years, but black will always be classic.

And while you’re at it, you might as well add another pair to the collection. CBK also loved the brand’s Callasli slingback sandals, which remain just as popular today (Hailey Bieber wore them to celebrate her 29th birthday just this fall).

A Black Dress: L’Agence Akiya Satin Maxi Dress

L'AGENCE Akiya Maxi DressL'AGENCE Akiya Maxi Dress

L’AGENCE

$395 at Lagence.com

Now for the perfect black dress, or three. With plenty of events to attend, a gown was a regular necessity for this woman. Somehow, each and every one she wore was so classic I wouldn’t be surprised to see a version of it on store shelves today. This pretty option from L’Agence reminds me of a black silk slip skirt the publicist wore once upon a time, and I think she’d be pleased with the simple scoop neckline as well.

The Long-Sleeved Shirt: Petite Bateau Long Sleeve Crew Neck Tee

Navy long-sleeve TshirtNavy long-sleeve Tshirt

Petite Bateau

$60 at Petitbateau.us

Another staple: simple, high-quality tees—Carolyn liked these from Petit Bateau, which you can still shop today. You’ll need a long-sleeve, a short-sleeve, and a tank-top (again, look for that that scoop neck). Pick up each in navy and white.

A Pair of Tall Boots: Vagabond Leather Tall Boots

Vagabond Leather Tall BootsVagabond Leather Tall Boots

Vagabond

$240 at Vagabond.com

Alongside the heels, Bessette could often be seen wearing a pair of perfectly worn-in tall leather boots. The brown buckled Prada pair she owned was extra special, and these similarly square-toed Vagabond boots remind me a bit of them.

A Bandana: Free People Graceland Solid Hair Scarf

Free People Graceland Hair ScarfFree People Graceland Hair Scarf

Free People

$24 at Freepeople.com

And then there’s the honeymoon bandana. Soft blue and easy as can be to throw in your hair, it’ll look cool with your sunnies, your gown a la Renate Reinsve at the European Film Awards, or your bootcut jeans. Or maybe you can wear it just to keep the tears out of your eyes while you cry watching American Love Story or reading What Remains? I don’t know. There are options here.

Read more:
Carolyn Bessette Kennedy wearing sunglasses and a headbandCarolyn Bessette Kennedy wearing sunglasses and a headband

Getty Images

Key Takeaways

  • Carolyn Bessette Kennedy’s classic style, which highlights lots of quality basics, is all the rage right now.
  • We found 11 of her wardrobe essentials that you can still shop today.

I don’t believe in capsule wardrobes, unless that capsule came straight from the mind of Carolyn Bessette Kennedy.

If I was shopping at Calvin Klein in 1990 and forced to choose between everything I own and 10 things the sales-associate-turned-publicity director fully approved of… it would be a hard choice, because I do like my things. Still, those 10 items would likely be all I’d ever need. I’d be a fool not to go for them.

As we obsess over a fictionalized version of CBK’s style every week on American Love Story, it’s nice to remember that many of the ’90s style muse’s favorite pieces still exist, whether in the exact format she found them in or new iterations. Even more excitingly: It’s so easy to work them into your own wardrobe. You don’t have to throw anything you own away, but maybe you’ll end up wanting to? One of the privileges of finding the perfect jeans or white button up or sunglasses is that you no longer need to shop around.

Keep reading to discover 11 (like I said, 10 is tricky!) CBK style essentials.

The Sunglasses: Selima Boutique Aldo Glasses

Selima Optique Aldo SunglassesSelima Optique Aldo Sunglasses

Selima Optique

$520 at Selimaoptique.com

Let’s start off strong with the exact sunglasses our muse held dear (and wore with every outfit). Selima Optique’s Aldo sunglasses (“the frame of choice of the ‘ultimate beautiful person’ as she was voted by her high school classmates,” they explain on their website) are available in four colorways. You can also get a slightly larger version called The Carolyn, or an even bigger pair named CBK depending on your personal eyewear size preferences.

The Headband: C.O. Bigelow Wide Tortoiseshell

C.O. Bigelow Wide HeadbandC.O. Bigelow Wide Headband

C.O. Bigelow

$40 at Bigelowchemists.com

Another exact match from early ’90s NYC: the headbands stocked at the famed C.O. Bigelow drugstore in Greenwich Village. The paparazzi spotted Bessette with her lemon blonde hair pulled back by one of these classic silhouettes more than a few times.

A Crisp White Shirt: Alex Mill Jo Shirt in Cotton Poplin

Alex Mill Jo ShirtAlex Mill Jo Shirt

Alex Mill

$145 at Alexmill.com

Oh, those tailored shirts. This is the sort of wardrobe essential that you might need to try a few options/sizes of—your perfect white button up might be different than someone else’s! But Alex Mill’s “100% crisp-to-the-touch cotton” selection is a perfect place to start. (It even has a little pencil pocket, which is incredibly chic.)

A Boxy Black Tote: Reformation Beatrice Tote Bag

Reformation Beatrice Tote BagReformation Beatrice Tote Bag
$548 at Reformation

Alongside her Birkin, CBK was often seen slinging Prada’s boxy Spazzolato tote over her shoulder. You can find them on resale sites, and fingers crossed another re-edition (they released one in 2022, and that was long before all this madness) is on its way. Otherwise, you could try a similarly boxy black bag! Reformation’s Beatrice has a great rectangular shape with the teeniest bit of slouch.

A Statement Jacket: Nour Hammour Althea Coat

Nour Hammour Althea CoatNour Hammour Althea Coat

Nour Hammour 

$3,200 at Nour-hammour.com

Truthfully, I could choose 10 jackets alone from CBK’s collection. She was so good about a coat, wearing options that ranged from delightfully oversized to fitted and belted, and sometimes even featuring a (rare) pop of color or print. This lengthy pony hair number from Parisian ready-to-wear brand Nour Hammour would feel right at home in the collection.

A Pair of Bootcut Jeans: Levi’s Wedgie

Levi's Wedgie Bootcut JeansLevi's Wedgie Bootcut Jeans

Levi’s

$110 at Levi.com

Bessette was a fan of Levi’s 517 bootcut jeans, a chic style introduced in the ’60s that is still sold in men’s sizing. Though the name is far less chic, the Wedgie jean is the modernized women’s bootcut style from the legacy brand. These are made with 1% lycra for a little stretch, so if you want 100% cotton, go for the 517.

A Practical and Chic Heel: Manolo Blahnik Carolyne

Manolo Blahnik Carolyne HeelManolo Blahnik Carolyne Heel

Manolo Blahnik

$995 at Manoloblahnik.com

Though these shoes were named after another famous Carolyn(e), socialite and designer Carolyne Roehm, Bessette helped put the almond-toed slingback on the map. It’s arrived in a thousand colors and finishes over the years, but black will always be classic.

And while you’re at it, you might as well add another pair to the collection. CBK also loved the brand’s Callasli slingback sandals, which remain just as popular today (Hailey Bieber wore them to celebrate her 29th birthday just this fall).

A Black Dress: L’Agence Akiya Satin Maxi Dress

L'AGENCE Akiya Maxi DressL'AGENCE Akiya Maxi Dress

L’AGENCE

$395 at Lagence.com

Now for the perfect black dress, or three. With plenty of events to attend, a gown was a regular necessity for this woman. Somehow, each and every one she wore was so classic I wouldn’t be surprised to see a version of it on store shelves today. This pretty option from L’Agence reminds me of a black silk slip skirt the publicist wore once upon a time, and I think she’d be pleased with the simple scoop neckline as well.

The Long-Sleeved Shirt: Petite Bateau Long Sleeve Crew Neck Tee

Navy long-sleeve TshirtNavy long-sleeve Tshirt

Petite Bateau

$60 at Petitbateau.us

Another staple: simple, high-quality tees—Carolyn liked these from Petit Bateau, which you can still shop today. You’ll need a long-sleeve, a short-sleeve, and a tank-top (again, look for that that scoop neck). Pick up each in navy and white.

A Pair of Tall Boots: Vagabond Leather Tall Boots

Vagabond Leather Tall BootsVagabond Leather Tall Boots

Vagabond

$240 at Vagabond.com

Alongside the heels, Bessette could often be seen wearing a pair of perfectly worn-in tall leather boots. The brown buckled Prada pair she owned was extra special, and these similarly square-toed Vagabond boots remind me a bit of them.

A Bandana: Free People Graceland Solid Hair Scarf

Free People Graceland Hair ScarfFree People Graceland Hair Scarf

Free People

$24 at Freepeople.com

And then there’s the honeymoon bandana. Soft blue and easy as can be to throw in your hair, it’ll look cool with your sunnies, your gown a la Renate Reinsve at the European Film Awards, or your bootcut jeans. Or maybe you can wear it just to keep the tears out of your eyes while you cry watching American Love Story or reading What Remains? I don’t know. There are options here.

Key Takeaways

  • Carolyn Bessette Kennedy’s classic style, which highlights lots of quality basics, is all the rage right now.
  • We found 11 of her wardrobe essentials that you can still shop today.

I don’t believe in capsule wardrobes, unless that capsule came straight from the mind of Carolyn Bessette Kennedy.

If I was shopping at Calvin Klein in 1990 and forced to choose between everything I own and 10 things the sales-associate-turned-publicity director fully approved of… it would be a hard choice, because I do like my things. Still, those 10 items would likely be all I’d ever need. I’d be a fool not to go for them.

As we obsess over a fictionalized version of CBK’s style every week on American Love Story, it’s nice to remember that many of the ’90s style muse’s favorite pieces still exist, whether in the exact format she found them in or new iterations. Even more excitingly: It’s so easy to work them into your own wardrobe. You don’t have to throw anything you own away, but maybe you’ll end up wanting to? One of the privileges of finding the perfect jeans or white button up or sunglasses is that you no longer need to shop around.

Keep reading to discover 11 (like I said, 10 is tricky!) CBK style essentials.

The Sunglasses: Selima Boutique Aldo Glasses

Selima Optique Aldo SunglassesSelima Optique Aldo Sunglasses

Selima Optique

$520 at Selimaoptique.com

Let’s start off strong with the exact sunglasses our muse held dear (and wore with every outfit). Selima Optique’s Aldo sunglasses (“the frame of choice of the ‘ultimate beautiful person’ as she was voted by her high school classmates,” they explain on their website) are available in four colorways. You can also get a slightly larger version called The Carolyn, or an even bigger pair named CBK depending on your personal eyewear size preferences.

The Headband: C.O. Bigelow Wide Tortoiseshell

C.O. Bigelow Wide HeadbandC.O. Bigelow Wide Headband

C.O. Bigelow

$40 at Bigelowchemists.com

Another exact match from early ’90s NYC: the headbands stocked at the famed C.O. Bigelow drugstore in Greenwich Village. The paparazzi spotted Bessette with her lemon blonde hair pulled back by one of these classic silhouettes more than a few times.

A Crisp White Shirt: Alex Mill Jo Shirt in Cotton Poplin

Alex Mill Jo ShirtAlex Mill Jo Shirt

Alex Mill

$145 at Alexmill.com

Oh, those tailored shirts. This is the sort of wardrobe essential that you might need to try a few options/sizes of—your perfect white button up might be different than someone else’s! But Alex Mill’s “100% crisp-to-the-touch cotton” selection is a perfect place to start. (It even has a little pencil pocket, which is incredibly chic.)

A Boxy Black Tote: Reformation Beatrice Tote Bag

Reformation Beatrice Tote BagReformation Beatrice Tote Bag
$548 at Reformation

Alongside her Birkin, CBK was often seen slinging Prada’s boxy Spazzolato tote over her shoulder. You can find them on resale sites, and fingers crossed another re-edition (they released one in 2022, and that was long before all this madness) is on its way. Otherwise, you could try a similarly boxy black bag! Reformation’s Beatrice has a great rectangular shape with the teeniest bit of slouch.

A Statement Jacket: Nour Hammour Althea Coat

Nour Hammour Althea CoatNour Hammour Althea Coat

Nour Hammour 

$3,200 at Nour-hammour.com

Truthfully, I could choose 10 jackets alone from CBK’s collection. She was so good about a coat, wearing options that ranged from delightfully oversized to fitted and belted, and sometimes even featuring a (rare) pop of color or print. This lengthy pony hair number from Parisian ready-to-wear brand Nour Hammour would feel right at home in the collection.

A Pair of Bootcut Jeans: Levi’s Wedgie

Levi's Wedgie Bootcut JeansLevi's Wedgie Bootcut Jeans

Levi’s

$110 at Levi.com

Bessette was a fan of Levi’s 517 bootcut jeans, a chic style introduced in the ’60s that is still sold in men’s sizing. Though the name is far less chic, the Wedgie jean is the modernized women’s bootcut style from the legacy brand. These are made with 1% lycra for a little stretch, so if you want 100% cotton, go for the 517.

A Practical and Chic Heel: Manolo Blahnik Carolyne

Manolo Blahnik Carolyne HeelManolo Blahnik Carolyne Heel

Manolo Blahnik

$995 at Manoloblahnik.com

Though these shoes were named after another famous Carolyn(e), socialite and designer Carolyne Roehm, Bessette helped put the almond-toed slingback on the map. It’s arrived in a thousand colors and finishes over the years, but black will always be classic.

And while you’re at it, you might as well add another pair to the collection. CBK also loved the brand’s Callasli slingback sandals, which remain just as popular today (Hailey Bieber wore them to celebrate her 29th birthday just this fall).

A Black Dress: L’Agence Akiya Satin Maxi Dress

L'AGENCE Akiya Maxi DressL'AGENCE Akiya Maxi Dress

L’AGENCE

$395 at Lagence.com

Now for the perfect black dress, or three. With plenty of events to attend, a gown was a regular necessity for this woman. Somehow, each and every one she wore was so classic I wouldn’t be surprised to see a version of it on store shelves today. This pretty option from L’Agence reminds me of a black silk slip skirt the publicist wore once upon a time, and I think she’d be pleased with the simple scoop neckline as well.

The Long-Sleeved Shirt: Petite Bateau Long Sleeve Crew Neck Tee

Navy long-sleeve TshirtNavy long-sleeve Tshirt

Petite Bateau

$60 at Petitbateau.us

Another staple: simple, high-quality tees—Carolyn liked these from Petit Bateau, which you can still shop today. You’ll need a long-sleeve, a short-sleeve, and a tank-top (again, look for that that scoop neck). Pick up each in navy and white.

A Pair of Tall Boots: Vagabond Leather Tall Boots

Vagabond Leather Tall BootsVagabond Leather Tall Boots

Vagabond

$240 at Vagabond.com

Alongside the heels, Bessette could often be seen wearing a pair of perfectly worn-in tall leather boots. The brown buckled Prada pair she owned was extra special, and these similarly square-toed Vagabond boots remind me a bit of them.

A Bandana: Free People Graceland Solid Hair Scarf

Free People Graceland Hair ScarfFree People Graceland Hair Scarf

Free People

$24 at Freepeople.com

And then there’s the honeymoon bandana. Soft blue and easy as can be to throw in your hair, it’ll look cool with your sunnies, your gown a la Renate Reinsve at the European Film Awards, or your bootcut jeans. Or maybe you can wear it just to keep the tears out of your eyes while you cry watching American Love Story or reading What Remains? I don’t know. There are options here.

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2026-02-24 15:10:38

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