Carolyn Bessette Kennedy, the mother of fall’s favourite ‘it-girl’ the ‘Sexy Posh’

By Tissa Sabeti

There is something undeniably sexy and sultry about confidence in being yourself, and Carolyn Bessette Kennedy (CBK) definitely dressed for herself, dressed for life and had that alluring messy-chic lived in look. With the resurgence of the 90s’ sleek seductiveness in our fall knitwear looks, more than ever, CBK’s elegant realness is at play in our wardrobes. 

 Max Mara’s – possible – nod to CBK in the opening of their Milan Spring/Summer 25 is loud and addictive as Ian Griffiths, creative director of Max Mara, puts us in a time capsule back to CBK’s appearance with JFK at the Whitney Museum’s black-tie dinner in 1999. 

The CBK style of a real-life busy woman in the city is transitioning into the 21st century world of the working woman embodied in the ‘Office Siren’; ‘the it-girl of the season’ according to asias.jpg on tiktok. ‘Sexy Posh’, a term which she coins , would pick up the sultry look of classic and dark brown button ups unbuttoned down to show her couture lingerie. She can be expected to lug around with her, in the most careless way, a large bag most likely in a dark and used suede, perhaps picking up the ‘demure’ and discreet Row Margaux as more low-key twist to CBK’s busy Birkin, especially since she does not walk into the shops to impress them, but rather demands to be impressed. Although the CBK style is a casual look, the ‘Sexy Posh’ also knows how to enjoy the  glamour of the night even if her office wardrobe is aimed at everyday practicality —  prioritising basics, but is never basic — as she, looking up to CBK, aims at her iconic undone sexiness. You might find in her signature wardrobe some unique vintage clutches and micro shoulder bags, bonus points for blacks, patents, East-West sleek and slender styles, and of course wherever the ‘sexy posh’ is suede is to be expected. With her it will always be either a structured and slim bag like the slice of lemon in her martini, or a slouchy bag, which serves undone and effortless like her nightwear which is probably silk and unstructured. 

While the others around her are imitating the Charlotte York look growing in popularity as her looks are reliably elegant and sexy, the ‘sexy posh’ CBK echelon are romanticising Natasha Naginsky with her sultry slim and arched brows and effortlessly chic energy and no funny business attitude. The ‘Sexy Posh’ like CBK will gravitate towards 90s brows and thin office turtlenecks with chunky statement jewellery to keep her observers eyes on her neck and the structure of her shoulders. 

With her it will always be either a structured and slim bag like the slice of lemon in her martini, or a slouchy bag, which serves undone and effortless like her nightwear which is probably silk and unstructured

With these looks the 90s’ ubermodel is also having a resurgence as Spring/Summer collections are bringing back the exposed long leg looks with micro shorts  (as shown by Max Mara’s Spring/Summer 25, look 43) that we expect from a 90s runway with Kate Moss. The super sheers are also back from the 90s which the ‘sexy posh’ will gravitate towards, styling  the sheer knitwear with suede blazers, and tights with micro shorts, and mesh shoes with heavy coats. The ‘sexy posh’ might be expected to reach for those classic ‘clueless’ knee socks but in sheers as the Cosmopolitan predicts in its May 24 2024 article ’20 fashion trends from the 90s that are back and better than ever’ by Lauren Adhav and Maggie Grisword. Although I think the  CBK ‘sexy posh’ will avoid this touch of Avant-garde styling such as alaia’s flats in fishnet and studs, the more maximalist ‘sexy posh’  city-trotter will not shy away from these bold shoes and prints such as cow print which she will probably be selecting over the leopard print as the latter is now growing in popularity and she wants to stand out. But one thing is for sure, almost all ‘sexy posh[es]’ will be lounging around their city properties in some form of sheer shoe and and even more revealing perfume which she will top-up like a nightcap before bed.

 But beyond the sultry coziness of her city house the ‘sexy posh’  fights the fall/winter cold with her outerwear styling bible: Jackie Kennedy x CBK. How Lush!

The ‘sexy posh’ has her eyes on the The Row and Prada this season for her  jackets and blazers, as big buttons and short cut blazer jackets are reemerging on the runway for that Jackie look, but you might expect a die hard ‘sexy posh’ in a real vintage 60s cut blazer jacket — and of course she will add some lacy elements and some rough leather details to keep her fans on their toes!

 On top, our ‘it-girl’ religiously follows CBK coat protocol: simple cuts and quality wool coats, throwing on a dark and structured double breasted coat or a waisted long line trench, yet she is always adding something of her own that gives her an Italian ‘sprezzatura’.

Image credit: Circle Vintage, John Mathew Smith via Wikimedia Commons