Bibliophile Style: Fran Lebowitz

Christopher Macsurak photo of Fran Lebowitz
Image credit: Christopher Macsurak / CC BY 2.0

Last month Netflix released Pretend It’s a City, a seven-part docuseries directed by Martin Scorsese about his friend and fellow New York MVP, Fran Lebowitz. In it, as she chats to an impressive succession of interviewers, Lebowitz covers some of her favourite subjects: books, jazz, modern manners, real estate, and, of course, New York. These comic musings are mostly intercut with archival imagery and footage of Fran in full flaneuse-mode walking the streets of NYC.

In these woman-about-town montages the signature Lebowitz aesthetic can be admired in its entirety. She is among those vanishingly rare figures who can be identified immediately from a mere silhouette. The poster for the show knows as much. It’s essentially a doodle of just two iconic features: that hair and those glasses. 

To compliment her famous bob and tortoise shells, Lebowitz always wears some combination of the same clothes. From top to bottom it’s as follows: A suit jacket from Anderson and Sheppard in their characteristically boxy fit, men’s shirts by Hilditch and Key (previously from Brooks Brothers before they stopped making the kind she liked), turned up selvedge Levi’s, and wingback cowboy boots. When it’s cold enough, she’ll add a topcoat (also from Anderson & Sheppard) and some tan leather gloves. On any given day she’ll top it all off with two gold rings and cufflinks.

Anderson and Sheppard shopfront
Image credit: Anthony O’Neal / CC BY-SA 2.0
Close-up of the label on Levi's jeans
Image credit: Abhidev Vaishnav on Unsplash
Collection of cowboy boots
Image credit: Megan Markham on Unsplash

Lebowitz has dressed this way for five decades. The only changes over time have been the disappearance of her monochrome crew neck sweaters, which she gave away en masse after deciding they were ‘childish’, and the penny loafers she switched for western boots. She started wearing her boots because of an ankle injury, but kept them around for the height they added to her 5ft 6in.

It may be tempting to mistake this simplicity and repetition for sartorial indifference. Far from it. It goes without saying that no one wears Savile Row tailoring incidentally and in Pretend It’s a City Lebowitz talks regularly about her interest in clothes. She confesses a hatred of money but a love of ‘things’, saying, among a litany of similar worldly passions: ‘I hate money, but I love clothes’. 

To the dismay of famed sports-lover Spike Lee, the thing that excited her most about being in the crowd at a historic fight between Muhammed Ali and Joe Frazer was that ‘the clothes were fantastic’. She says:

‘It was a very wonderful fashion and cultural event. Unfortunately, there was a fight in the middle of it.’

Fran Lebowitz

Anyone who has read Lebowitz’s views on yoga pants or her love of Anderson and Sheppard will not be surprised by the comfort with which she steps into the role of fashion historian. In Pretend It’s a City, she tracks the curious trajectory of Ralph Lauren’s career, in which his clothes, initially made to imitate inaccessible WASPy raiments, are eventually worn by those selfsame WASPs. What’s more, they wear his clothes rather than the ones he imitated to begin with. The rich and powerful in Ralph Lauren polos: it’s a silk-stockinged snake eating its own tail, an oofy Ouroboros, and Lebowitz describes it all with characteristic wit. 

While the credits roll on the second episode, she tells Scorsese about her cufflinks, which were hand-made by the artist Alexander Calder. She fondly speculates about their origins and recounts how they come to be in her possession. It’s a candid moment — off the cuff, even — which goes a long way to revealing Fran’s reverence for the magic that can be contained in the material. 

Fran Lebowitz standing in a crowd on the street
Lebowitz at a plaque unveiling at James Baldwin’s former residence in NYC
Image credit: Village Preservation (Greenwich Village Society for Historic Preservation) / CC BY 2.0

Lebowitz’ uniform seems to encompass some essential parts of her character. The custom-made shirts and tailored jackets gel with her professed love of ‘things’. Her lifelong bookishness dovetails with the Ivy-style Shetlands and penny loafers of her youth. And her no-nonsense directness and cut-the-BS attitude are perfectly mirrored by the utilitarian durability and punk aesthetic of old school Levis and cowboy boots.

The look — like Fran herself — is entirely self-made. It’s hard to imagine anyone else pulling off the apparent contradiction of wearing ranchwear with French rounded cuffs off Jermyn Street. But there’s no question that on Lebowitz it not only works but has become iconic. Her wardrobe is a curious contradiction, combined to form a uniform, and somehow turned into something gestalt.

For all fans of Fran and her fashion, long live the Lebowitz look.

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