Fran Lebowitz and the Appeal of Formulaic Dressing

On the many charms of wearing (almost) the same thing every day.

February 2, 2021 9:31 am
Fran Lebowitz and the Appeal of Formulaic Dressing
Gabriel Serrano

Recently, while stepping outside for my daily walk, I put on a simple roll-neck, with my most loved trousers and a pair of loafers that have been worn in to the extent that they remind me of wearing slippers. It was a seamless look that could go anywhere and do almost anything. If things were open, I could go from breakfast to bar all in one day and never look out of place. Immediately, I thought, “Why can’t I just always wear this exact same outfit?” But could I really wear the same thing every day for the rest of my life? The truth is, it’s unlikely for the simple fact that I like my clothes too much. But since finishing Pretend It’s A City, the docu-series sequel to Martin Scorsese’s HBO documentary film on Fran Lebowitz, I am now convinced that I could actually do it someday. 

At this point, a few weeks after its release on Netflix, a whole new generation has been made aware of the author and public speaker’s grumblings about the state of things in our society — so much so that copies of Metropolitan Life are selling on eBay for over $300. They’ve also become aware of her iconic choice of clothing as she stomps through the streets of New York. The tortoiseshell spectacles she insists have been co-opted by Warby Parker. The Levi’s with the Cowboy boots and oversized French-cuff shirts worn, most famously, with tailored jackets from Anderson & Sheppard in London. There’s no shortage of writing documenting her reliance on these items, her “uniform” if you will. 

In an article Lebowitz wrote for the Financial Times she refers to this not as a uniform, however, but as a “formula” which suggests greater nuance and purposefulness. It suggests that within her established framework, there is room to play. Someone like Steve Jobs, for example, had a uniform. He wore the exact same black turtleneck and dad jeans every single day. What separates Lebowitz is that she found a series of items that, at their core, worked together and over time, evolving with her tastes, allowed her to indulge in her love of clothes through slight variation. 

Yes, she’s always wearing a jacket, but some days, the jacket might be navy with a windowpane check. Other days it might be pistachio green or a boating stripe. Maybe the shirt is pink instead of white. Either way it’s always a french cuffed shirt, and the jacket is always from Anderson & Sheppard.

Fran Lebovitz classic outfit
Gilbert Carrasquillo / George Pimentel / Walter McBride

It can be frustrating when people or magazines try to suggest rules for dressing. It never works, because people change and most of the time so does their taste in clothing. Personally, as a fairly young man, I’m constantly trying out new things to see what does and doesn’t work for me. Only recently have I decided to go for gold button blazers after being terrified of them for years (They used to remind me of Carlton from Fresh Prince). In the back of my mind, though, I suspect I already know what I really like.

Lebowitz says she got to her formula at some point in her 20’s. By the time her first book was published, in 1978, she had it pretty much set in stone. I remember looking at the dust jacket on the back of an old copy (which I should’ve picked up at the time, given how much they’re going for on eBay right now), and her famous scowl was still there alongside the Levis, a checked jacket and cigarette. The biggest difference was that the shirt looked to be an Oxford button down — probably from Brooks Brothers before they became everyone’s punching bag. As time has gone by, it seems Fran has since merely upgraded the quality of those same core items to better suit her changing tastes. 

What makes this simple outfit so striking, though, isn’t who made the individual pieces or even what color they are, but the fact that Fran Lebowitz has presence, which is something which most people lack. Having a wardrobe made up of the same clothing that signifies you is a great concept. It frees you up to focus on the more important things in life, like your personal character or what instrument to learn next week since you’ll probably still be stuck at home. Admittedly this hasn’t worked with Fran since she is supposedly still dealing with a decades-long writer’s block, but not having to worry so about what clothes to wear at least affords her extra time she can spend finding things to complain about. The point, though, is that this approach allows those other aspects of her persona, and her life, to take center stage, without the distraction her sartorial choices might cause.

Discovering your own formula is key here. To start, you’ll have to identify the items you think of as basics, and then commit to sticking with those and investing in the best possible versions. From there, play with things like color and texture, or even silhouette if you’re so inclined, but never to the point where it causes others to do a double take or you to wonder if you can “pull it off.” After a year, there’s no telling what you will have accomplished with all the time you’ve saved. I, for one, am considering learning how to play Giant Steps on the tenor sax.

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