17 Simple, Classic Pieces If You’re Sick Of Your Wardrobe And Want To Dress More Like Carolyn Bessette Kennedy
by The Candidly Team
More than perhaps any other woman, when we look back at the luminous Carolyn Bessette Kennedy, we are astonished by how every outfit she wore in 1999, would make her the chicest person in any room today, 25 years later.
We get a fair amount of hate when we invoke her iconic and enduring fashion, as if it’s trivial to discuss the clothes of someone who died so young. But Carolyn’s now seminal wardrobe is, in part, why people still talk about her and write about her today.
So in a sea of fashionable celebrities, why does she stand out?
Well. Carolyn dressed very simply. Everything she wore was trend proof and classic. She barely wore jewelry. And every piece fit impeccably.
See? She just had an eye. She only ever seemed to use 2 different purses, and there’s a story that even though she bought a Prada ski suit, she asked them to remove the logo.
Being remembered for your outfits 25 years on isn’t trivial. It’s art. Clothes can be art. And if Carolyn were alive today, she may have launched her own line of impeccable basics, and we would have been writing about them now. But today we settle for a list of 17 pieces from some of our favorite brands—who we would bet have also been inspired by her sartorial choices—all chosen to reflect her classic simplicity.
1. J.Crew Garçon classic shirt in cotton poplin
We must start with a crisp, white button down shirt. And this one in poplin cotton and with elongated cuffs means you can wear it to your fanciest events or with jeans.
Price: $98
2. Quince 100% Washable Silk Maxi Skirt
With a truly astounding price, this WASHABLE silk skirt is a full maxi on most of us who aren’t model-height, and we love it paired with the shirt above.
Price: $80
3. Dolce Vita Odela Heels
The point, the open sides, the unbelievable comfort, the low, unassuming heel—these are the fancy black heels you can actually walk (or dance) all day in.
Price: $120
4. Quince Cotton Modal Muscle Tank
A perfectly cut muscle tank can make a simple pair of jeans look unbelievably chic.
Price: $15
5. Madewell Kick Out Crop Jeans
Annnnnd these are the jeans. They are that classic, cropped, bootcut style that we all love and yet, can never find. A mere bonus is that when you slip them on for the first time, they feel as though you’ve had them forever.
Price: $138
6. Margaux The Flat Sandal
The brilliance of Carolyn’s footwear was that it was always impeccable, but also clearly comfort was a priority. Her go-to sandals were Prada and out of our price range, but this brand Margaux makes exquisitely made shoes that are so mind-blowingly comfortable you sort of won’t believe it. Yes, we sacrificed the heel but we still feel city-sexy in these flat sandals with all the visible foot showing through.
Price: $225
7. Z Supply Modern Slub Tee
A simple, tissue-thin, perfectly cut t-shirt is an essential. And this is our favorite.
Price: $39
8. The Kit High-Rise Wide-Leg Utility Trouser Jeans by Pilcro
Actual carpenter jeans are flattering on almost no one, but these near-magic jeans were recommended to us by one of our readers who called them the “real life sisterhood of the traveling pants” and we were SHOCKED by how well they fit and flatter. Shocked.
Price: $148
9. J.Crew Gwyneth pleated slip skirt
Truthfully, we never saw Carolyn in a full skirt, but this tight-pleat and camel color is so chic and so minimalist-cool, we had to include it. The comfort in the elasticated waist is unmatched—especially on period day when you just want to wear your jammies but also have to go to work and “see people.”
Price: $64.50
10. Marcella Yvonne Top
Quite simply, the perfect, stretchy black top that looks good with literally everything. That big wide neckline is deeply flattering, and the extra long sleeve makes your entire upper body look long and lithe.
Price: $78
11. Marcella Vesey Pencil Skirt
And of course a perfect black pencil skirt is required. This one is our favorite because it’s beautifully stretchy.
Price: $88
12. The Soleil Slim Strapless Ruched Dress
Little known fact: strapless is actually MORE flattering than sleeveless. And this dress hits at the perfect spot under the arm that magically does NOT create lumps and bulges. The stretch crepe fabric glides over the tummy and the rump to create a gorgeous hourglass on literally any body type. It’s truly our favorite LBD.
Price: $170
13. Marcella Olympia Bolero
Subtly inspired by Carolyn’s sheer gloves worn during the most beautiful wedding dress moment perhaps in history, this bolero takes any outfit to stratospheric chicness levels. We also love it when we’re feeling self-conscious about our arms in warm weather but don’t want to sweat in long sleeves.
Price: $78
14. Marcella Norah Blazer
A black blazer is also one of those must-have, quiet luxury staples. And this one is somehow both oversized and therefore comfortable for layering, but also gorgeously cut and therefore makes us look polished.
Price: $245
15. Madewell Medium Silk Bandana
A bandana for greasy hair is a genius way of looking supremely stylish, while not succumbing to the lazy bun every, single day of our non-bathing lives. And there is no brand making better cotton bandanas than Madewell. We have maybe 14? We also roll them up lengthways to create a headband-y look.
Price: $48
16. The Junie High Rise Wide Leg Flare Pants By Maeve
Sleek, wide-leg, form-fitting, black pants that move with you is an essential component of an elevated-basics wardrobe. This one is our favorite. It also comes in cream, which seems scary, but isn’t.
Price: $128
17. Quince Mongolian Cashmere Crewneck Sweater
A cashmere pullover is a classic girl’s best friend. This flawless one from Quince costs 3-4x less than anywhere else, which means we get to buy it in 3-4 colors, no?
Price: $50
BONUS: THE ACCESSORIES
Evita Peroni Wide Headband
Carolyn bought her plastic headbands at C. O. Bigelow in NYC, but we love this brand easily found on Amazon because they don’t give us a headache.
Price: $38
Le Specs Outta Love Sunglasses
Perhaps the one giveaway that her style was honed in the 90s is these sunglasses she wore. But, since the 90s are back, we love them.
Price: $65
L.L. Bean Boat and Tote® Open-Top
There are so many new bag companies that make fancy leather goods or logo-filled monstrosities. This basic, perennially perfect L.L. Bean canvas bag was a pragmatic favorite of Carolyn’s, proving that sometimes, most of the time in fact, the simple choice, is the best choice.
Price: $35
At The Candidly, we try a lot of stuff so you don’t have to. We only recommend things we truly love, and that we think you’ll love, too. All products are chosen independently by our creative team, and all details reflect the price and availability of products at the time of publication. If you buy something we link to, The Candidly may earn a commission.
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