The Menswear of Leonard Bernstein & Maestro (2023)

Despite spending a lot of time talking about orchestral music, I actually don’t have much experience with Leonard Bernstein.

I actually hesitate to call myself a fan of classical music, simply because I lack proper education and exposure to what are probably considered the tentpoles of the genre. If anything I am a John Williams obsessive. Thankfully for the purposes of taste and not remaining in a bubble of film score (which is often bemoaned as nothing more than orchestral pop music to most classical heads and critics, even if the style is symphonic), Williams has amassed quite a bit of concert and celebratory work; it’s necessary for me to talk about his concertos and fanfares for fear of people reducing me to just listening to Star Wars or E.T .

In little 12-year-old Ethan’s completionist journey to obtain every non-film piece Johnny has ever written, I came across a work called For New York (Variations on Themes of Leonard Bernstein). Despite critic John Rockwell calling it “feathery and flashy” in a 1988 NYT article, I found the piece incredibly remarkable. It’s quite modern and not exactly straightforward, with Williams going between a few techniques with rhythmic chord interjections that are quite characteristic of Williams’s later works; it’s hard to believe this was written in 1988 when he was still in his big movie mode. 

After some digging, I learned that the recurring motifs were indeed the themes from the titular  “Leonard Bernstein”.  This “Lenny” (the original title of the piece was called “To Lenny! To Lenny!”) must have been someone quite special if my favorite composer was honoring him. I would later find out that Williams would honor him again with Highwood’s Ghost, which is based on the stories Lenny would tell Williams about the Tanglewood being haunted.

Imagine my surprise when I later found out that Lenny was considered not only one of the greatest conductors of all time but also quite responsible for helping make classical music more accessible and understandable to young people. 

Lenny conducting the Boston Symphony Orchestra in Mahler’s Symphony No. 2 in July 1970. Photo by Heinz H. Weissenstein.

Ever since For New York, I have slowly expanded my appreciation of Bernstein. A lot of it has to do with West Side Story, which I first saw (the 1961 one) in college in a music appreciation class and later fell in love all over again with the release of the  2021 Spielberg version. It was the latter that helped inspire me to take a more serious look at his composing work; I’m particularly a big fan of his overture to Candide (I saw the full musical at a solo Dapper Day event years ago) and especially his  Dialogue for Jazz Combo and Orchestra (the Allegro movement), as it makes good use of interjections and “random” jazz-esque runs that I love from Williams. 

Of course, nothing beats watching footage of the man actually conducting, whether it’s for his work or others. In the grand scheme of things, he is mostly known for the latter, as he has performed and recorded so many of classical music’s great works. Whether it’s a video of him in the 60s or the late 70s, you’ll immediately note that he is incredibly expressive, with big smiles and exaggerated gestures. It’s not just for show, as each articulation brings out an equal expression in the orchestra, producing the specific sound that he believes is best by his interpretation of the score. It probably helps that Lenny was known for also being quite close and informal with members of the orchestra, which made for an intense collaboration. A good analysis of Lenny’s conducting style can be found here

My first real dive into Lenny came with Absolutely on Music where Seiji Ozawa (a current maestro) speaks about his experiences as Lenny’s assistant conductor with the New York Philharmonic. (That book talks about numerous classical works, which was also helpful for me to dive deeper into classical music). Ozawa-san’s memories later lead me to watch Lenny’s appearances in the  Young People’s Concerts, The Unanswered Question, as well as his extended interview with the Kennedy Center. I’d say that the former two were quite helpful when I started to move into menswear philosophy and focused on relating menswear to music and other expressive art forms. 

A plaid jacket and a foulard tie. How Ethan!

On that note, it also helped that Lenny was a stylish man, furthering my one sided, amateur kinship with him.

Lenny didn’t have a strict uniform (unlike John Williams who seems to perpetually wear a black turtleneck/crewneck), but it is clear that had a consistent vibe and ease about him. He rocks tailoring with aplomb, whether it’s a dark 60s ensemble with a pinned club collar , a 70s flared suits, stiff white tie (for performances) or unbuttoned safari shirts, sweatshirts, and cleavage-displaying popovers (which he seemed to have gotten obsessed with in his later years). With his use of trad, rugged casual, Going Out, evening wear (as well as white tie for performances) , and everything in between, its as if Lenny was able to wear the whole swath of everything we like from menswear. It is clear that he had a penchant for clothes!

What makes him even more notable was the fact that he was able to look incredibly natural (and delightfully slouchy) no matter what his outfit he was wearing. He wasn’t only in suits or casual wear; he wore it all! Being so stylish while being so clearly immersed in his work (and chain smoking) is quite a vibe…and proof that anyone can do it. Decision fatigue be damned! I’d venture to say that this effortlessness in all manner of dressing is echoed by (or even emanates from) his relationship with music. He’s able to wear the boldest or charmingly sloppy clothing with just as much ease as conducting any concert piece. It’s always cool to see someone who has a great style while still having a creatively demanding “main job”. With all the videos of him talking about music, I just wish I had something regarding his thoughts on fashion. I wonder if he would have said something about dressing for expression.

Being able to talk about Bernstein’s conducting and his clothing is all due to his status as one of the world’s most famous conductors. In other words, Lenny was quite widely documented not just in televised concerts but through press and numerous photographs. He was quite the socialite; Tom Wolfe wrote about one of his parties for New York Magazine, in which Wolfe makes sure to specifically describe Bernstein’s attire: “a black turtleneck, navy blazer, Black Watch plaid trousers and a necklace with a pendant hanging down to his sternum.” 

I believe that my admittedly still limited experience with Lenny closely echoes my desire to expand my musical taste beyond Williams and to enjoy music for music’s sake.  I assume that my experience is quite similar to various people in the 60s-80s when Lenny was most active (and who may have seen him in person). As a result, Most of the pieces in my “non-film score” playlist on Spotify are conducted by Lenny, which include my favorite pieces by Mahler, Copland, and Prokofiev.  

This is also why I’ve made it a point to try and have a “tangible” experience with classical music by going out to live concerts. This helps me get more connected to a piece of music; it feels more personal than simply going through a checklist. Overall, classical music is still a relatively new thing for me (and not too regular due to high ticket prices if I miss the $20 youth ones) but I’ve really enjoyed it. It’s similar to having Isabel, a true art lover, help guide my appreciation of painting and poetry– Lenny was my way in for classical music. 

As you could expect, I was quite excited to see Maestro, the new biopic about Lenny and his wife Felicia Montealegre, who was an accomplished performer (actress in various media) in her own right. After seeing Tár, which brilliantly showed the complexities and beauty of conducting in a wild story about power and being “canceled”, I was keen on seeing how Bradley Cooper (who directed and starred in this film) would do it. After all, Lenny’s whole thing is about interpreting and expressing music, which I believed would be quite interesting to juxtapose against his dual role (or struggle?) as a conductor and composer as well as his affairs with men and women throughout his life. Since Tár was able to reference Lenny multiple times, I assumed Maestro would be it

Unfortunately I was wrong. I found the final film a slight notch above mediocre. It’s quite similar to Napoleon in that it just feels like we’re seeing scenes of the subject’s life without any context to why they deserve the attention to begin with. Cooper’s Bernstein is lauded by numerous characters in-film and these social accolades (and his indifference to his conduct) are one of the major causes of strife between him and his family.  However, we are simply told that he loves music and that is what makes him a good conductor. 

We do not get any scenes of Lenny’s philosophy on conducting or how he achieves such a significant expressive sound from the orchestra. The most we get are a few (admittedly cool) scenes of Bradely doing a good job mimicking Bernstein’s distinctive conducting style. Tár has cool conducting scenes, but we also get at least a few scenes of explanations of what expression and conducting means for music that are amazingly accessible for any viewer. Tár’s unabashed intellectualism on music is what makes it such a compelling and interesting film; Maestro’s deficit of this makes Cooper’s Bernstein feel incomplete.  

This isn’t helped by the film’s inability to go into the pressures that come between being a performer (conductor) and a creator (composer). There is one scene where Cooper’s Bernstein remarks his dissatisfaction with his small body of original work, but that sadness (or lack of summer) seems to just go away when he see him easily compose his Mass without any mention of how being a performer may get in the way of creating. It would’ve been fine if they didn’t allude to this dichotomy a few times.

The saving grace of Maestro is found in the performances of Carey Mulligan (who plays Montealegre), the beautiful cinematography, and of course the menswear. Even if Cooper’s Bernstein feels a bit half baked, there is no doubt that he fully contains the drip of the real life Lenny. 

Costume designer Mark Bridges, who has previously done other period films like The Artist and Phantom Thread, did an incredible job with this film. Not only are there clear distinctions between the different decades that span the story of the film, but there is also close attention to how Lenny himself would have dressed in those eras.  In that way, the film, serves as a great case study for the numerous expressions of classic and vintage menswear, much like the real life Leonard Bernstein.

In some cases, film-Bernstein’s attire seems to be either reproductions or close riffs on actual documented outfits worn by IRL-Lenny.  As a result of this effective costuming, nothing comes across as  fake or costume-y, whether it’s the bowties in the late 40s, the slick suits of the early 60s, bolder patterns and flares of the 70s, or his crazy casual style as an old man in the 80s. Cooper looks extraordinarily slouchy which almost makes you wish he would take some cues from the character he played and apply them to his actual style.

Cooper playing Lenny in the early 1940s.

I just realized that I spent all this time writing about something that is actually a bonus episode for our Patreon patrons (I also don’t have much else to say lol). It’s actually a really good one that gets into more detail and discussion on the film and its style, making it hopefully be worth the $5 admission. You can listen to the first few minutes of our bonus episode on Maestro below! You’ll have to subscribe on Patreon to get the RSS feed of the full episode (as well as access to our Discord, which is the main reason people join.

I do want to finish this by saying that I am still very excited to get even deeper into classical music, both old and contemporary (like Thomas Adés). While the film wasn’t amazing, it did inspire me to entertain the idea of making more time for music.  Prior to watching the film, I had actually completed fully fleshing out and orchestrating a piece for my girlfriend, which I am incredibly proud of (especially because it makes full use out of the orchestra and gets to have a Prokofiev/Williams vibe). I want to do more! 

Like film-Bernstein, thinking about my small catalog of original compositions, does make me a bit sad.  I love menswear and still devote a lot of my time to talking about it, but music was and still is my main love. 

I guess Summer still sings in me, even if it isn’t as often as it did in high school and college. In other words, the days before I found menswear, photography, and writing. What a time!

Recommended Reading

Lenny sure looked good in a suit.
Aaron Copland with Leonard Bernstein, circa 1940. Good use of the DB and a bowtie.
Classic 40s look.
Houndstooth!
And now a boating blazer? Lenny clearly liked clothes.
Shame about the Windsor knot though.
He looks great. A stellar example of a well dressed creative.
Lenny wearing separates when he was named musical director in 1957. According to the original caption of this image, he was the first American-born conductor and second youngest to hold the post.
He clearly had a thing for houndstooth. Check out his wholecut loafers too!
He liked bow ties too.
Felicia and Lenny with Donald L. Cox, Field Marshal for the Black Panthers in Jan, 1970 photographed by Stephen Salmieri.
Lenny in what seems to be a DB cardigan in the 1960s, photographed by George Talbot.
The artist at home, wearing wholecut loafers.
Bernstein and Felicia in 1957.
A dark brass button blazer and a cig.
Club collar and slim striped tie. Note the triangle pocket square!
Leonard Bernstein, Judy Garland and Merle Oberon by Otto Rothschild. I really like that he wasn’t afraid to wear a bow tie.
Bernstein during a visit to Finland, 1959 still wearing a bowtie.
Big scarf and coat energy.
Leonard Bernstein photographed by Erich Auerbach.
A button-down collar!
One of the coolest photos not just of Lenny, but of all time. A plaid DB suit (with patch pockets) and what seems to be a nice coordination (but not matching) between tie and pocket square. Just look at how at ease he is! That’s what we should always strive for whenever we wear clothing.
Morning dress-esque?
Leonard Bernstein conducting in 1988. Love the dark suit and striped tie.
Paisley tie with a three piece and cape.
The cape yet again, worn over a suit with double-faced, single button closure.
Lenny in a quad-patch pocket suit with a contrast collar shirt and floral tie (and not-matching pocket square). Copland has a more subdued ensemble, though his tie seems to have some sort of crest motif.
Corduroy suit!
A 1970’s version of separates utilizing horsebit-esque loafers.
Bandana with a chambray button-down collar. Photo by Michael Grecc.
Bernstein also looked at ease with tuxedos and white tie. Here he is after the Gershwin Memorial Concert in March 1946. Photo by Heinz H. Weissenstein.
Post-performance in 1967. Photo by Ken Heyman.
He was like a movie star! I like the use of a fun pocket square with a tuxedo.
Leonard Bernstein at a party with Betty Comden, right, in 1949. Photo by Stanley Kubrick.
Bernstein wearing a dinner jacket and cape. He’s so cool.
Leonard Bernstein during opening night party at Roseland for the stage production West Side. Photo by Avery Willard.
Leonard Bernstein, Glenn Gould and Igor Stravinsky, January 4, 1960. All at easy in tails. Photo by CBS Photo Archive.

Johnny and Lenny.
John Williams and Leonard Bernstein at Harvard Night at the Pops, June 6, 1989
I could only dream to look this cool.

A satin bomber jacket over black tie. Amazing.
Even after looking at ease in suits and tuxedos, Lenny still retained a great casual style. Here is as a very young man photographed by William P. Gottlieb.
Striped shirts and big trousers. A classic menswear staple.
Here he is doing the striped undershirt move with a sportshirt.
It’s a move he kept doing late into his life.
Sportshirt!
Untucked even!
Lenny was after expressiveness.
Bernstein conducting a Tanglewood Music Center orchestra rehearsal in 1955 wearing white buck loafers.
OCBD over a turtleneck.
The tied sweatshirt. Photographed by Stanley Kubrick for Look Magazine in 1949
It’s interesting to note that despite being casual, he still used accessories all while retaining a slouchy demeanor.
That being said, he was also known for simply wearing a turtleneck on its own.
It might be his most iconic “uniform” outside of evening wear.

Wild stitching on that flannel jacket.
Here’s another look of that outfit that shows how the stitching continues down the sleeve!

Leonard wearing a cool jacket, perhaps commissioned in his youth (as it looks like an older style despite his age in the photo).
Turtleneck and exploding pocket square while rehearsing at The Albert Hall in 1973.

Turtleneck under a sweatshirt? What a move!
Leonard Bernstein photographed in NYC in 1978 by Jack Mitchell.
A bandana and striped tee.
Looks like he’s done this combo before, but sans beard.
Not a bandana, but an untied knit bow tie.
Fun sweater.
In fact, it seems he liked sweatshirts. This Mahler one is amazing.
He also had one with “Harvard” in Hebrew on it!
Lenny. Photo by Michel Ginfray.
Lenny in some sort of anorak thing.
Popover collared sweatshirt and a striped tee.
A chambray popover and big sunglasses.
Big workshirt over an OCBD.
Of course, I would be remiss if I didn’t show his beloved safari shirts. He seemed to wear these quite a bit in his late life.
It looks like he owned a few variations of this style of shirt.
Seiji Ozawa and Lenny.
Leonard Bernstein in a madras shirt and flip flops, photographed in his studio at his home in Fairfield Connecticut in August 1988.
Cozy Brenstein.
Even stylish guys need to have some homewear!
Let’s talk about the movie! This outfit doesn’t actually appear in the film proper, but its very cool: a geometric tie, TV-fold pocket square, and a flecked 50s-esque jacket with odd trousers.
For all its faults, Maestro does get the aesthetics of Bernstein quite correctly. Here he is in a DB suit and plain tie, worn when he steps in to conduct.
Composing in a bowtie (in the bathroom, no less).
He does look like an old movie star.
Nice spearpoint collar and geometric tie. I’d wear this (just without cuff links).
Based on the tie, this seems to be what the scene’s attire looked like with color.
In one of the Tanglewood scenes, he wears a collar less jacket. While this may seem modern, this style of garment did exist back then as a form of novelty leisurewear.
Cary Grant wears one in The Philadelphia Story.
Sailor attire for a surreal sequence where he performs in his own Fancy Free.
A flecked tweed jacket and abstract tie help set this scene in the mid 1940s.
As we move on to the late 1950s, his suit lapels get trimmer and his pocket squares get more like a TV. 
The monochromatic styling as well as the jacket’s lapels does a good job of sending up the correct era.
Coats and bowties! This actually reminds me of an old fit I did back in 2020.
I guess he makes a good case for grey suits!
At a late 60s party, film-Lenny wears a peaked lapel checked suit with a paisley shirt and dark pocket square. It does feel quite like something the real Lenny would wear.

His new pal Tommy wears a six button DB jacket and a turtleneck. There’s a line in the film that shows film-Lenny’s appreciation of it!
Interestingly, film-Lenny later wears a similar red turtleneck and a brown guncheck suit. It’s one of the coolest outfits in the film that feels quite Bernstein.
A bit of Red Oni, Blue Oni here.
The fit that most people enjoy is the 70s khaki suit with tonal socks and single monks. I could have sworn I’ve seen an actual photo of real-Lenny in this fit but I unfortunately couldn’t seem to find it for this blog post.
It’s got all the details: pleated and flapped patch pockets, an extended waistband, a slight pagoda shoulder….
and a bi-swing back!

We don’t get a full look of it, but film-Lenny does wear a tuxedo. This is during the premiere of Mass.
For the iconic Ely Cathedral performance of Mahler No. 2, he gets to wear a tail coat…with exorbitant amounts of sweat.
Casual Lenny gets it’s first appearance as a ribbed tank and unbuttoned dress shirt. Compare film-Lenny’s sloppy look with Copland’s more “put together” combo of a spearpoint and checked tie.
He looks like an SFC model with this sportshirt over a ribbed tank.
Cool glasses here!
He wears them again with this epic plaid sportshirt with solid sleeves.
A home look with a chunky cardigan and white turtleneck. Very cozy!
The classic turtleneck Lenny is seen during a rehearsal. He wears a grey turtleneck with slim brown trousers (with frog pockets) and jodhpur boots. A very slick late 60s look!
Popover Lenny.
They use those single monks with the khaki suit later on!
They reproduced his “Harvard in Hebrew” sweater for the film!
A terry cloth polo worn to finish Mass.
Like the popover outfit from earlier, he wears the polo with khakis.
A very casual outfit: a long sleeve Breton stripe tee with flared jeans and sneakers.
And a navy bandana as an accent.
Beard Lenny gets another 70s zip number, this time as a jumpsuit, worn to do some coke.
Of course, it wouldn’t be Lenny without some safari shirts. Interesting to make it up in orange reverse stripe!
A nice blue flannel version. The gold watch pops against the cloth!

Casual dad Lenny in a simple sweater and jeans.
For the Tanglewood composer seminar scene, he wears the iconic white safari shirt.

And while participating in bacchanalia, he wears some sort of three-pocket shirt. It doesn’t seem to be the same safari shirt from earlier.
I do want to shout out the well-done costuming of the side characters and extras. Really great 40s styling here!
A cool zip polo with a ribbed collar that is sure to make SFC-heads jealous!
A very interesting 40s tie with what looks to be a 40s suit.
Aaron Copland wearing a sportshirt, hollywood jacket, and neckscarf! I’ve gotta do this look now that I have a proper hollywood jacket.
Serge Koussevitzky (played by Yasen Peyankov) wears a pinstripe suit and bowtie.
DB and bowtie here too! Theater (kid) energy?
The extras were all wearing true vintage. One of the articles I linked state that the filmmakers had to ship (or rather truck) over hundreds of vintage pieces from LA costuming houses to NYC, which was where the movie was filmed.
Nice late 60s looks on the left. A brown jacket and blue pants are a cool move.

This interviewer has a cool look, wearing a light brown tweed jacket with a paisley-ish shirt and turtleneck base layer.
More extras with cool outfits,!

Tommy, one of Bernstein’s muses, wearing what seems to be a cool take on the cricket sweater.
Mendy Wager (played by Zachary Booth) wearing a flared tuxedo. I rather like the idea of wearing a blue shirt with black tie!

If only we could party with Lenny.

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Buh-bye!

EthanMWong | StyleandDirection

The Podcast is produced by MJ.