90s Style Icons to Emulate who are NOT Carolyn Bessette Kennedy
You won't pull off the CBK look--but you might be able to emulate these other fashion mavens of the '90s.
Everyone, from various Substackers to Vogue is talking about how to get the Carolyn Bessette Kennedy (hereby known as CBK) look, popularized by the new series, Love Story, which follows the relationship of Carolyn Bassett Kennedy and JFK Jr. Demand for CBK-adjacent clothes is so high that old Calvin Klein dresses are selling for—wait for it—$20,000 on eBay (per Viv Chen)
And let’s be real—as gorgeous as the late Carolyn Bessette Kennedy was, most of us don’t look anything like her, and in our effort to “get the CBK look,” we will find some dumpy knee-length pencil skirt, an oversized white shirt, kitten heels, and then walk around giving LOFT realness. Per Anna S., you won’t be able to get the look so easily just by wearing the same clothes.I saw this happen when everyone was desperate to “get the Shiv Roy look” when “Shiv Roy” mostly looked that way because she had red hair and a huge, perfect ass. So while CBK’s look was obviously very cool, most of the people aiming for that (let alone spending tens of thousands to do it) won’t achieve it.
But if you’re anything like me, you don’t want to be like everyone else. So what’s a girl to do if she wants to emulate some classic ‘90s sophistication, but doesn’t want to be just another CBK clone?
May I suggest these other fashion icons from the ‘90s.
Cobalt blue is big for 2026, and who better to ring in this trend than the late, great Margaret Thatcher? Get her look with a pleated midi skirt, structured bag, and let’s not forget a cute single breasted blazer.
While we are all enjoying the various fruits of the worldwide web, let’s not forget the man who invented it—and his legendary fits. If you want to dress like the Grandfather of the Internet, Al Gore, all you need is a green utility shirt, a pair of wide-leg beige trousers, and coordinating leather shoes and belt. Can someone say? ZZZZZRF EE-OO EE-OO (sorry, that’s the dialup sound.)
Maybe he wasn’t able to find the lost treasure of Al Capone, but he was able to cultivate a great normcore aesthetic! Get Geraldo Rivera’s look with a simple cobalt sweater, khakis and some dad sneakers!
If you’re a millennial or zoomer, you likely know Rosie O’Donnell for her long-standing feud with Donald Trump. But once upon a time, she was a fashion icon. Get her sleek gray suiting look with a pop of red collar.
Who could forget Dan Rather’s voice on the evening news and his investigative journalism? More importantly, that trench! Get Dan Rather’s iconic Sherlock Holmes inspired fit with a good cashmere scarf, a 100% cotton trench, and let’s not forget a pop of tweed with some Vince trousers.
Menswear is so hot right now, and what could be better than an unexpected burst of red amidst subtle lilac and black? These shades are fit for a king…Larry King! Emulate the great media legend with this elevated fit.
Does anyone remember the OJ trial? If you do, you probably remember Kato Kaelin, the bizarre “house guest” who somehow managed to live with both Nicole Brown Simpson and OJ Simpson, separately, without sleeping with either one. The King of Squatters. A veritable Dupree of You, Me and Dupree.
All you need is some light-wash straight leg jeans, black oxfords, a white button-down layered under a pinstripe vest, and you’ll be serving “I haven’t paid rent in months to my landlord or her ex-husband who I somehow lived with next and now I’m a witness in a murder trial.”
Kim Jong Il ran North Korea with an iron fist—and you’re about to serve some iron cunt. Get his look with a sleek boiler jumpsuit, oversized gold glasses, and a chic satchel meets crossbody.
'You can't actually look like someone just by wearing the same clothes' is advice that should be given more often.
Do not, do NOT make me want to dress like Dan Rather. Because now I want to, and I am not sure anyone in my life or my suburban enclave would understand it one bit.
The handbag pairings are utter genius here, although I personally think Larry King would go for a crossbody.