The Thoughtful Accessories

"In a way, Carolyn Bessette Kennedy was the original street style icon. While her special-occasion looks were always effortlessly elegant, the candid photos of her on the street in New York City are the ones I reference when I need my own sense of sartorial inspiration—especially in the fall. Kennedy's accessory game was unmatched. She would often pair her well-tailored wool coats with tortoiseshell headbands, oversized bags, and knee-high leather boots of the highest quality. Eagle-eyed fans will be looking for these details come airtime." — Bianca Betancourt, culture editor

Va-Va-Voom in Versace

"I love this bright white tweed Versace gown that Carolyn wore to the Fire & Ice Ball in Los Angeles in 1998. It's a silhouette that would still stun today. Her sleek blowout and classic red lip pulls the entire look together. This photo also serves as a reminder that Carolyn's hair was a powerful accessory in its own right!"— B.B.

The Wedding Dress

"I think one of the most iconic outfits to nail is her wedding look—it’s obviously one of the most important moments for the couple. Designed by Narciso Rodriguez, this simple white silk gown fit like a dream, and the sheer gloves and matching veil add a layer of elegance. The tailoring of the dress, the quality of the fabric, the construction of the garments—these are the details that make the difference between something off-the-rack and custom-designed couture. It’s all about the execution!"— Olivia Alchek, senior designer

The Statement Outerwear

"Whenever I think of Carolyn Bessette Kennedy’s style, a few iconic pieces of outerwear immediately come to mind—each one adding an elegant, statement-making touch to her otherwise minimalist wardrobe. There was the red belted Prada coat, one of the few boldly colored items she regularly wore, and the furry black Anne Demeulemeester piece, but nothing beats the leopard-print coat she was famously photographed in while walking her dog and JFK Jr. by her side. Styled simply with blue jeans and black heeled boots, it remains the perfect example of how a single bold pattern can elevate even the most pared-back look. It’s effortlessly cool, distinctly ’90s, and quintessentially CBK."— Ariana Marsh, senior features editor

The Feminine Dresses

"You might picture Carolyn Bessette-Kennedy in crisp neutral tops and deconstructed Yohji Yamamoto coats, but from time to time, she proved she was also a fan of a great print. (Just turn to her snakeskin Prada heels or her plaid winter coats for proof.) One of my favorite things about CBK is that she knew how to make looking fabulous seem easy, and often that can be accomplished with the perfect dress. In this paparazzi shot, our quiet luxury queen wears a Chanel by Karl Lagerfield design pulled from the house’s 1996 Cruise collection. The playful piece features a bright pattern of hand-drawn flowers in pink, purple, and yellow. Bessette-Kennedy dressed up the youthful design with some of her usual luxurious accessories, including a patent leather shoulder bag and some strappy slingbacks with bows on the toes—both in black."—Joel Calfee, assistant editor

The Sleek Denim

"Carolyn Bessette-Kennedy’s wardrobe was full of designer pieces, from Helmut Lang and Calvin Klein to Yohji Yamamoto and Jil Sander. But her day-to-day looks—in particular, this casual dog-walking outfit—prove that you don’t necessarily need to break the bank to make a statement. All you need is an eye for elegant shapes, quality materials, and timeless staples. Jeans and a sleeveless black knit top will simply never go out of style. And those strappy multi-colored Prada heels? Well, those are just for fun."— Chelsey Sanchez, editor

The Gala Glamour

"One look of CBK's that always comes to mind is the one she wore to the White House Correspondents’ Dinner in 1999: a structured black suit, a low bun, a red lip, and this incredible Jean Paul Gaultier clamshell necklace that made the entire outfit. It was sleek and minimalist, but bold at the same time, which is exactly what I love about her style."—Rosa Sanchez, senior news editor

The Uniform

"The allure of Carolyn Bessette-Kennedy’s style goes far beyond just her fashion sense, but there’s something to be said about her clean, minimalist, quiet luxury-coded style that has had such an enduring effect on fashion. When I think about the perfect fall outfit, this look immediately comes to mind. The formula is all about investing in key pieces that can serve as the building blocks in your wardrobe. Start with a black cashmere sweater, style it with a camel wool midi skirt, and then finish it off with a pair of complementary brown leather boots and a sleek black tote (by Prada, of course). It’s professional, it’s classy, it’s timeless—and it’s so CBK."—Julie Tong, Senior Commerce Content Lead