By Caroline Reilly

I’m not an expert in many things, but if there are two Jeopardy! categories I’d dominate, they’d be Menswear and Men Over 50. (More on the latter here.)

Now you’re probably asking yourself the obvious: What gives me, a woman, the credibility to craft this list? For starters, I used to work in high-end men’s suiting; my favorite party trick is guessing a man’s jacket size with razor-sharp precision. I’m also the descendant of a tailor who made suits for FDR. And I come from a long line of female menswear aficionados — my grandmother and namesake used to wear tailored overcoats from the Barney’s mens department long before androgynous clothing was more readily available, and she kept a box of silk ties to have at the ready for gifts. Whenever we go shopping, my mother and I always stop off in the men’s department to browse the wool sport coats and pick out our favorite ties from the spreads laid out on the deep mahogany shelving. 

Menswear fascinates me because it is largely formulaic: a dance of proportions and lines, textures and patterns. An exceptionally dressed man, in my opinion, is marked by an understanding of how to follow and step outside those formulas, achieving a trademark style that isn’t ostentatious or trendy. A well-dressed man’s clothing doesn’t stop the eye; it fits on their frame like a puzzle piece, suiting both their body and their personality. In crafting this list, I wanted to avoid focusing exclusively on the men who garner the most attention for their clothing — the ones who top red carpet “best dressed” lists or have made a name for themselves as impressively styled gents. Instead I wanted to focus on the men who have cultivated a signature look over the space of decades, whose personal style has evolved not in response to trends or fads, but to match their dignified personas. All the men on this list know the secret to dressing well is knowing what you look like — what you really look like — and then building a wardrobe that flatters it, rather than trying to wear what’s “in style.” Their clothes fit them both physically and metaphorically. 

So without further ado, here they are: a definitive list of the best dressed men over 50.

For years, Bong Joon Ho has been dressing in wardrobe basics: tees, trousers and jackets in monochromatic hues. And it’s his loyalty to simplicity that lands him on this list. Monochromatic dressing is delicate — you need to make sure the hues you choose flow into each other instead of clashing, and this is something he has mastered: pairing navy shirts with black jackets, including greys and browns with intention but restraint. His style has been largely unchanged for most of his career, which speaks to the value in this kind of dress; he makes the case for investing in a few key wardrobe staples to be worn again and again for years. 

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Harvey Keitel

Harvey Keitel style can best be classified as quietly sexy. Since his Mean Streets days, he has been rocking air ties and breezy, open button-downs; pleated trousers and oversized blazers — all to a smoldering effect. These days, he loves a good black on black or navy on black look, knowing — as many of the men on this list do — that you can rarely go wrong with monochromatic. And he tops every look off with his signature frames: tinted acetate Persols that radiate a sense of cool befitting a former Reservoir Dog.

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Cornel West

Cornel West has been committed to the same look for decades. And considering how sharp he looks every single time you see him, he makes a strong case for having a signature outfit. For West, it’s the three-piece suit. Throughout his career, he has favored a black three-piece suit, complete with a waistcoat and often a pocket watch. He adds even more character with a signature scarf and french cuffs.

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Al Sharpton

We’ve talked about Al Sharpton before: I listed him among the best dressed men in election coverage and I stand by that call emphatically. Sharpton knows how to take risks: bold patterned suits, vibrant colored ties and pocket squares, double-breasted jackets with wide peak lapels. And he pulls everything off not only well, but with ease. And despite his trim physique, none of it overpowers him, instead only amplifying his presence. With Sharpton it all comes down to tailoring — not a single item in his wardrobe puckers or pulls where it shouldn’t. Everything looks as if it was crafted specifically for his frame. 

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Michael Caine

So I know at the outset of this list, I promised not to include men who were famous for their style, but it felt like blasphemy to leave off Michael Caine, who quite possibly invented style. Whether it’s his iconic heavy frame glasses or tweed suits, there was literally never a day that Michael Caine got up and put on anything less than superlative. He is the quintessential Englishman; I’d be hard pressed to believe he’s not a regular at at least one Savile Row tailor. If you’re a young guy — or really a man of any age — looking to upgrade your wardrobe, simply Google Image search Michael Caine, close your eyes and point and buy the entire outfit your finger lands on — you cannot go wrong.

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A man should dress in a way that you don’t notice. He looks good and you don’t know why. But it’s the tailoring, the materials, and the clothes. — Michael Caine

Jet Li

As I was going through archival photos of Jet Li to prepare for this list, I was struck by one near universal decision he makes: foregoing a tie. Li’s bold collar choices alone warrant his spot on this list: nehru collars, air ties, crew-neck tees with three-button blazers. This is in part a testament to his ability to balance these fashion risks with safer wardrobe elements like subdued hues like deep blues and blacks.

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Sam Elliott

Sam Elliott is a fucking fox and always has been. And you’d be forgiven if you’ve been too entranced by his luscious head of white hair or knee-weakening mustache to notice that the man is also a top-notch dresser, but never fear, I’m here to set the record straight. Elliott’s style is part ranch owner, part collegiate; he loves mid-rise trousers, but often opts for a straight leg black jean in place of slacks. Easy pocketed button-downs, Western belts and tweed blazers are all staples in his wardrobe; even on red carpets he wears modern cut suits, and sometimes foregoes a suit altogether for a sport coat on trouser combo, never deviating from his cool-guy vibe.

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Eugene Levy

I want to be clear about something: by and large, I think classic fitting suits and clothing are the way to go. So you can imagine how impeccably dressed Eugene Levy must be to make this list with a wardrobe of almost entirely slim-cut suits and clothing. As Johnny Schitt on the Emmy winning series Schitt’s Creek, Levy is one of the best dressed guys on TV, pulling off impeccably tailored navy and grey suits and crisp white shirts with aplomb. His clothing offscreen deviates little from this blueprint. On red carpets, Levy who is often accompanied by his equally sartorially superlative son, Daniel, wearing some of the most precisely tailored slim-cut suits I’ve ever seen. His casualwear is equally neat, leaning toward slim jeans and crisp white shirts layered under crew-neck sweaters. And he’s not afraid to be playful either: his signature glasses and his penchant for colorful suits match the lightheartedness of his comedic genius.

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Carlo Ancelloti

Ok full disclosure here — I know absolutely nothing about soccer, but when I was compiling this list it was suggested to me that I should include some sports-adjacent people as sports are apparently kind of a big deal. My editor and some more sports-minded friends directed me to the men of soccer; the Euro appeal of the sport no doubt means the athletes retain slightly more style than, say, Bill Belichick, whose entire wardrobe should be burned for fuel. Ancelloti was among those suggested to me, and when I saw him, the game was over. First of all, let’s be clear, the man is very hot. Second of all: the man can dress. When I was researching him I couldn’t believe how many pictures there were of him wearing a perfectly — and I mean perfectly — tailored three-piece suit to a soccer game. For his more casual looks he opts for long sleeve knit polos, often under blazers in neutral and deep hues of navy and dark blues, which is a timeless and versatile look, and one every man should supply some variation of.

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Alan Cumming

Alan Cumming is a man who seems inoculated against any notion of over-the-top; whether he’s wearing leather pants and a tank top, a kilt or a velvet suit, Cumming manages to make a statement without looking like he’s doing a bit. Because that’s who he is, right? He’s radical, he’s edgy, he’s sexy and he’s a troublemaker. And throughout the years his look has evolved to reflect his ever-changing sense of style — bleached hair one year, a buzzcut the next. These days he’s squarely in the silver fox category, though, and still sporting some seriously devilishly good looks.

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It’s important to have your own sense of style and to understand that it’s about how you want to be perceived. —Alan Cumming

David Lynch

If you’ve ever admired someone’s air tie, you have Lynch to thank. Lynch defined men’s fashion in the ’80s and remains an absolute icon to this day. He’s someone who manages to always look perfectly in style without ever looking trendy, and this is because he abides a simple principle: less is more. Lynch most often opts for minimal outfits: full black suits, grey jackets and white shirts, typically buttoned all the way up, sans tie for his signature look. Like many of the men on this list, he opts for a more classic fitting suit; no quarter-break trousers for him, or narrow lapels. Simply clean lines, easy structures and slightly left-of-center flourishes. And it’s a testament to his taste that despite his style remaining largely unchanged since the ’80s, Lynch remains a fashion standout. 

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Bryant Gumbel 

Who ever said newscasters had to be stuffy or boring? Not Bryant Gumbel, that’s for sure. The television journalist ranks among not only the most finely dressed men in news, but in media and television writ large. He knows exactly how to walk the line of traditional with a bit of flair: a tie bar adorns a simple but perfectly tailored navy suit; a crew-neck sweater is paired under a tweed jacket instead of a button-down; bold ties; even a fur lapel to gussy up an otherwise reserved cold-weather look. These carefully selected details ensure he stands out from his more cookie-cutter colleagues without looking overdone.

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Jeff Bridges

Jeff Bridges is a hunk — always has been, always will be. His mane of hair and sweetheart eyes have secured him hearts across the nation, and his sense of style lives up to his charm. Like his acting chops, Bridges’s fashion sense is versatile — some days he’s in a slick suit (usually a classic fit, and sometimes with an offset feature, like a unique hue or a white tee instead of a shirt), other days he looks more like The Dude: comfortable jackets, casual knits and shirts. But no matter how Bridges is dressed, he looks at home in whatever he wears: happy and confident, with a warm, cordial energy.

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Gustavo Matosas

Ok I’m gonna be honest — this was another one that I found by way of asking folks for suggestions in the sports world. But as soon as I saw Gustavo Matosas, my first thought — after “Is he married?” — was he absolutely must be on this list. Matosas can wear a suit, boy can he. His cleanly tailored, rich navy slim-cut suits look like he’s been poured into them, and by pairing them with a simple white shirt, as he often does, he avoids looking like he’s trying too hard, an all-too-common pitfall when wearing European-cut suits. His sport coat game is pristine as well, as he often pairs them with denim jeans or offset color trousers that always sit low on his hips — just an impossibly sexy look. Despite all his clothing fitting perfectly, he always looks a touch disheveled from animatedly waving his hands and yelling orders (I assume? I don’t know how soccer works) at his players, which only adds to his appeal; even under exerting circumstances the man wants to look good, and for that, we salute him.

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Lenny Kravitz

A lot of the men on this list I would suggest emulating — I think there are staples in their wardrobes that every man should have and that every man can pull off. But sorry kids, Lenny Kravtiz is not that guy: trying to mimic his style is a real attempt-at-your-own-risk situation, unless you are … well, Lenny Kravitz. When it comes to style, Kravtiz is a man who needs no introduction; his signature leather pants, aversion to shirts that cover his chest (no one is complaining) and knack for layering statement jewelry, scarves and an enviable collection of sunglasses all amounts to a look that if you saw it disembodied on a mannequin you would know — in an instant — belonged to him.

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For me, clothing is just another way to express, outwardly, who you are. —Lenny Kravitz

Eric Ripert

Eric Ripert’s off duty-looks are very down-to-earth: sport coats and jeans, half-zip sweaters and slacks. Despite his casual charm, he’s a man who always looks like he’s just come straight from the ironing board. But what lands Ripert on this list is how absolutely pristine he looks in his chef’s coat; sure, it’s his uniform, but something about the combination of his ocean blue eyes, steely grey hair and immaculate white chef’s coat is just … delicious.

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Harrison Ford

Harrison Ford is the quintessential cool guy, which owes in large part to his style, which has remained god tier for the entirety of his career. As a young actor, Ford cornered the market on casual clothing: mid-rise light-wash jeans, sport coats over buttoned-up knit polos. If you’ve been on menswear Twitter at any point over the last few years, you’re bound to have seen the photo of him in short shorts and boat shoes. Ford’s style — somewhat of a cross section of collegiate chill and “if Indiana Jones were a layperson” — remains the same today, sporting Western belts and tousled grey hair as his two trademarks.

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Donald Sutherland

Donald Sutherland’s style is the absolute perfect amalgamation of collegiate and bohemian; for every picture of him in a tweed sport coat or dark suit, there’s one of him in a long leather coat with shaggy hair. Sutherland’s ability to shape-shift from English-lit professor you definitely have a crush on to hippie who gets you high and then plays Dark Side of the Moon is iconic, and it’s that versatility that has defined him through the decades. His tall and lanky frame makes him ideal for layered looks — button-downs under sweaters under sport coats, overcoats over heavy knits — and it’s this playful yet distinguished aesthetic that makes him an obvious pick for our list.

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Jacques Pepin

Jacques Pepin has the corner mark on cozy chic. Whether he’s cooking in his home kitchen for his Facebook page or making an appearance on a panel or red carpet as an expert in all things French cuisine, Pepin’s wardrobe is the clothing version of his cooking: warm and unpretentious but refined and timeless. Standing at his kitchen counter, Pepin favors soft flannel shirts, lush knits and comfy button-downs. For more formal appearances he wears traditional but playful suits — opting often for a bowtie instead of a tie, or even the occasional ascot. When he’s not in a suit, Pepin can be found in a rich wool sport coat, soft cotton jacket or even a vest. Just as his food spans the intricate to the simple, Pepin’s wardrobe has a look for all occasions, be it cooking dinner at home or attending a formal gala, and chances are he’s the best dressed guy in the room every time.

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Larry David

Larry David’s style has evolved throughout the years, but his staples remain the same: simple tan slacks, luxurious knit tees and polos, and soft-shoulder sport coats that he layers over practically everything: half-zip sweaters, button-down shirts, knits … you name it and Larry wears a soft sport coat over it. Full disclosure, I’m at a slight advantage in talking about David’s wardrobe; last year I spoke to Curb Your Enthusiasm’s costume designer for Vulture about how she dresses Larry, who I deemed a casual fashion icon. She told me that Larry wears a lot of his own clothes on set, noting that how things feel often dictates whether or not they get the stamp of approval from him. He prefers neutrals and solids, and long sleeves over short — he’s a man who knows what he likes and sticks to it.

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“Jerry [Seinfeld] said I dressed like an Upper West Side communist.” —Larry David

Denzel Washington

Let’s be honest: Denzel Washington could be wearing a potato sack and he would look good, which makes it even more notable that a man with his superlative looks goes through the extra and frankly unnecessary trouble of actually dressing well; when he rolls out of bed and already looks better than 99.9% of the population. Washington is a cool guy, but not the kind of guy that thinks himself cool, which makes his style all the more admirable. For years, he’s been sporting boxy sport coats and tweed overcoats like he invented them; at awards shows he is the quintessential Hollywood star: impeccably tailored tuxedos and that million-dollar smile. Casual Denzel is no exception; whether he’s sitting courtside at a basketball game or being snapped by the paps going through his day, he’s almost never without his New York Yankees cap, a perfectly fitted leather jacket and jeans that look so good on him you’d be forgiven for thinking he invented denim.

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Tim Curry

Can you talk about well-dressed men without talking about Tim Curry? I think not — the camp icon has proved himself a style giant on and off screen for decades. Seventies Curry could be found in everything from patterned shirts and shearling bombers to rugby blazers and skinny ties that radiated English and impish charm. Despite his high-styled roles, throughout the years Curry kept it simple but not boring: think double-breasted blazers over T-shirts, sateen shirts and matching neckties. These days, Curry sticks monochromatic, as so many of the men on this list do. In his black turtlenecks with black slacks, he remains subtly but undoubtedly stylish.

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José Luis Rodríguez

José Luis Rodriguez is a man who knows how to dress with flare without looking garish. He takes fashion risks without looking overdone. His impeccable style through the years is equal parts sensual crooner and impossibly cool. He pulls off patterned suits and sport coats with ease, three-button suits, pattern socks — the man does it all. The one consistent is that he tailors everything to his relatively trim frame with perfect precision, which elevates every outfit from stylish to refined and sexy. And it doesn’t hurt that he has that head of perfectly coifed hair.

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Mikhail Baryshnikov

There’s not a single pair of tights on this earth that could not be immediately improved by having Mikhail Baryshnikov’s god-like body in them; pairing them with just a white tee and leg warmers, as he often did, Baryshnikov managed to make warm-up clothes look high fashion. But his off-duty looks are just as alluring: Nehru-collared jackets, double-breasted suits, roomy button-down shirts that mirror the way his hair perfectly falls around his chiseled face, mid-rise trousers that accentuate a waistline tapered from years of dance. Everything he wears oozes class without stuffiness, his boyish charm amplified by clothing that, even off stage, looks as if it’s meant to move.

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Vincent Cassel

Vincent Cassel always looks like he just stepped off a yacht in the south of France: slightly disheveled but dripping in resort wear from elite designers that don’t scream money but rather whisper wealth, as the saying goes. Soft linens, close-fitting polo shirts — the man even wore a cream suit with a lavender button-down sans tie to his wedding, and he looked absolutely pristine. Cassel wears clothing that moves; in photos of him strolling with his new wife, everything on him seems to flow perfectly with his gait. But make no mistake, this doesn’t mean anything he wears looks messy or oversized. The simplicity of his French aesthetic — he opts for neutral tones, and pairs staples like crewneck sweaters with impeccably fit trousers — combined with the obvious luxury of everything he wears means that even his most basic fit appears tailored to his frame.

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I’m an actor, that’s what I do every day. Dressing up is part of my job. But whatever you wear you should always be yourself: never go totally with the fashion but use what there is available to be an individual. —Vincent Cassel

Anthony Hopkins

Anthony Hopkins is one of those quietly well-dressed men who has been doing it right for decades. As a young man he looked like your quintessential Welsh boy, layered in fair isle sweaters, corduroy sport coats and heavy wool scarves. This look is a far cry from the kaleidoscope of print shirts Hopkins often wears in his Instagram and TikTok videos. Still, Hopkins looks fantastic, whether he’s painting and conversing with his cat Niblo at his Malibu home or looking dapper as the face of Brioni. Perhaps in due credit to his status as one of the finest actors of a generation, there is little Hopkins can’t pull off; the same daring energy Hopkins brings to his iconic characters, he brings to his closet, whether it’s a straw fedora and summer-weight suit or a heavy wool windowpane sport coat accented by a long printed silk scarf. 

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Richard Lewis

Someone once asked me why I wore so much black clothing and I joked that I always wanted to be funeral ready — a sentiment I’d like to think Richard Lewis, a fellow neurotic and monochromatic icon, would relate to. Lewis has been rocking almost entirely black outfits for the entirety of his career, but make no mistake, these are not black tees and jeans. They are oversized boxy jackets and wide leg trousers, Nehru-collar overcoats cut almost like tunics, and three-button suits that I typically would advise against for anyone who doesn’t have height on their side. With Lewis, the devil is in the details: an off-center zip or button on his jacket, his iconic collection of colorful sunglasses, the choice to forego a real tie for an air tie. When I interviewed the costume designer for Curb Your Enthusiasm, she told me Lewis is a uniformed dressing enthusiast, the kind of guy who keeps multiples of the same staples in his wardrobe. At the beginning of last season, he requested a run of black-and-white T-shirts from John Varvatos. 

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Steve Buscemi

Buscemi holds a special place in my heart on this list; he’s quite possibly my favorite man in the world — I would trust him to hold my drink any day of the week, and I feel like just 10 minutes spent looking into those globular eyes and talking about my problems could possibly cure my every ill for good. He just seems safe. When it comes to his dress, he’s unpretentious but tailored: he sticks to neutrals but mixes them, pairing navies and other deep blues with blacks and greys. Buscemi’s look says he’s not so ego driven that he craves being the center of attention, but he’s self-respecting enough to look good for himself and those around him. His look is one I think most men can and should emulate. And I’m walking the walk here: shortly after watching his Park Bench series, I bought my dad a plain navy baseball cap like the one Buscemi wears throughout the seasons, and for a recent family gathering, I made my him wear a black button-down under a navy blazer — a Buscemi staple — and he got quite a few compliments that day.

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Willem Dafoe

Willem Dafoe’s simple, cool and artistic style makes him an obvious but oft under-appreciated member of the best-dressed men club. Dafoe tends towards monochromatic looks — navy on black, black on black — but don’t for a second think that means his aesthetic is anything approaching boring. He loves a navy tux with black accents, a black turtleneck or a grey suit and black tee — simple but incredibly refined looks that are always perfectly tailored to his trim frame. What these simple but tasteful foundational pieces do is allow Dafoe to look put together and classy without overpowering his face, which is a work of art that needs little embellishment.

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Christopher Walken

Christopher Walken is one of those guys who has been wearing some variation on the same outfit for the last 50+ years. And who could begrudge him for it? The guy always looks great. Early in his career Walken embraced an almost gangster-adjacent style; double-breasted jackets with wide lapels, pinstripe suits and neutral but flowing scarves. These days you most often find Walken in some sort of fuller-fit suit that retains much of his youth’s charm, though he still opts for a double-breasted cut and wide lapel, and arguably holds the all-time record on how many times someone can pull off pinstripes, which requires a delicate balance of bravado and tailoring. He pairs these somewhat dressy suits with black dres or T-shirts sans tie to remind you that at the end of the day, he’s far from a traditional dresser (or guy).

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I never buy clothes … Whenever I do a movie, all my clothing is from that movie set. They don’t give me anything. I steal. —Christopher Walken

Brian Cox

Brian Cox plays one of the most well-dressed men on television in his role as Logan Roy on HBO’s Succession, but his off-duty style is just as noteworthy, albeit not quite as traditional. Over the years, Cox, whose style is distinctly Scottish (the man wears a kilt like it’s ready-to-wear), has never met a patterned sport coat he couldn’t pull off. Almost all his outfits have one through line — modern tailoring with a twist — like the aforementioned patterns, a bold color or lapel buttons that transform your average sport coat into a sort of Barbour-esque motorcycle jacket/suit jacket hybrid. He’s one of the few older gents on this list who routinely opts for less classic tailoring — closer fitting jackets and narrower lapels — and it’s a testament to the precision with which all his clothing fits (and English tailoring, let’s be real) that it looks as timeless and refined as any classically tailored getup.

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Andy Garcia

What can one say about Andy Garcia? The man is aging like a fine fucking wine. His style is what I can only classify as earthy and sumptuous: rich camel coats, heavy brown tweed sport coats, round tortoiseshell frames and lush overcoats that make him look like the older man who might catch your eye at intermission at the opera. Garcia is another guy who prefers more classic tailoring, but he relaxes each look by foregoing a tie or opting for an easy but crisp white button-up opened at the top. And while he does dress in navy and other cool tones, it’s the browns and other warm colors that really make Garcia’s style shine.

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Spike Lee

Spike Lee’s style is, in a word, iconic. Decades into his career and I don’t think there’s been a bad look in the bunch, which is honestly a small miracle considering how familiar the man is with fashion risks: bold colors, eccentric pairings, and a flair for accessories are all mainstays in his wardrobe. Lee’s style — his whole aesthetic, really — is the beautiful serendipity that happens when a man is not afraid to have fun but knows when and how to tie everything together. This is thanks in large part down to Lee’s taste; he knows how to layer accessories like hats and jewelry without overdoing it, and at the core of all his outfits is fit: suits that are tailored to perfection, proportions that flatter his frame and color combinations that feel like candy the eye.

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Steve Martin

When I started writing this list, Steve Martin was the first name that came to mind. For years, my mother, an avid fan who insists he is also quite sexy (as I get older, yeah, I see it) has long sung the praises of how Steve Martin dresses. And she’s right. Over the years, Martin has mastered the art of looking effortlessly refined, and the secret is all in the fit. Martin is a classic-fit guy through and through; you will never see a no-break trouser or a puckering shoulder, and rightly so. Martin is a three-button-suit loyalist. And this is a real don’t-try-this-at-home-kids kind of thing — a three-button suit requires the proper stature and a very good tailor. But Martin is a masterclass in how to make it work, choosing the right textures that look refined without looking flat, and usually pairing them with simple items like a white shirt or contrasting tie. Early in his career, Martin paired scholarly tweeds with mid-rise pleated trousers and managed to still look young and cool, and that’s because he never appears like he’s trying to look young or cool. Last year when he was on the Late Show with Stephen Colbert he wore a rich — almost plum-toned navy — suit that hung loose from his frame. It looked expensive and timeless. He paired it with honey acetate framed glasses and a simple white shirt and blue patterned tie. Alongside Colbert, whose suits are almost without exception too tight and too short, it was immediately apparent why Martin has the reputation for dressing well that he does.

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Elton John

Elton John is a man who’s style needs no introduction. It is hard to find the words to adequately appreciate the journey this man has taken our eyes on over the years: rhinestones and sequins, platform shoes and vibrant lucite sunglasses, feather boas and theatrical hats. For those unacquainted to John’s earlier works, long before he was the man in technicolor suits, his look was squarely ’70s Brit. At the beginning of his career (think his “Your Song” era), he wore bell-bottom jeans and knit sweaters and caps, but it wasn’t long before his style evolved into the candy-coated spectacle we see today. John is an icon, so much so that any single item in his wardrobe can be easily identified as his. Here, try it: close your eyes and picture a brightly colored pair of clear sunglasses adorned in rhinestones. Whose are they? And that’s why he’s on this list.

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“I probably have about 10,000 pairs of glasses and they’re either in the warehouse or in the house. You always end up wearing the same thing.” —Elton John

John McEnroe

As you might have guessed by this point, I’m partial to more classic style tailoring. I think low-rise trousers and slim-cut jackets all have a time and place, but generally speaking I find them at best trendy and at their worst repellent. John McEnroe, however, makes a strong case for keeping things trim. Whether he’s on the court in his short shorts or doing commentary in a European-cut suit complete with low-rise slim trousers, Mac’s clothes rarely leave much to the imagination. But he’s not in it for the glamor or getting named on best-dressed lists like these; he’s simply dressing for his body type and personality. McEnroe’s lean athletic frame is pretty easy to dress, and hard to make look unsightly, but I think what ensures that he really pulls off his slimmer cuts is who he is: impish (some might say prickly) but completely unpretentious. He always looks slightly disheveled — not messy, per se, but just unbuttoned enough to radiate sex appeal. He’s not wearing slim-cut suits because he takes himself too seriously or because he fancies himself a trendsetter, but because presumably they’re comfortable, and he thinks they look best on him. And he’s right, they do. 

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David Letterman

David Letterman was another guy who came to mind immediately when I set out to write this list. Letterman is no Cary Grant, but he’s one of those guys who’s sexy and you kind of can’t figure out why. He’s got a devilish charm and obviously a good sense of humor, but more than that, the man has style. Growing up, sitting down to watch Letterman every night was a ritual, and at the top of every show, as he’d walk out with his double-breasted suit swinging on his trim frame, my mother and I would remark on how nice he looked. He usually opened the show with his jacket still buttoned, which gave his incredibly expensive suits an easy, worn-in feel. Even in his modern single-breasted suits, Letterman opts for a more classic fit; pants that look almost too big in their billowing. But it’s his dry sense of humor and presence that allows him to pull this look off without looking like an uptight banker. His attention to detail also makes a difference: loafers, white socks and round glasses that look like they were molded for his face.

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Sam Waterston

Sam Waterston is what I would call “professor hot.” With his round acetate glasses and messy white hair, I’d sign up for those office hours in a heartbeat. Waterston’s style ranges from the understated and collegiate (heavy tweed coats) to slightly kooky (the bow ties he often pairs with his suits). Like the man, everything is gentle — soft fabrics, soft lines — from oxford shirts to pullover sweaters. But don’t be fooled: underneath that delicate veneer is a man who wore a distressed leather moto jacket and red frame glasses to a recent climate change protest with Jane Fonda.

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Graham Norton

British TV presenter Graham Norton’s style has a flair all his own; if some guys on this list look good in everything, Norton takes sartorial risks that few could pull off. Velvet jackets, bold patterned shirts and suits, and color combinations most men could only dream of wearing. Norton’s clothing, though bolder than many of the men on this list, is noteworthy for a number of reasons. First of all, it’s fantastic. Second of all, true to his Irish roots, it’s all tailored to perfection. And third, what lands Norton on this list in part is what has landed so many men on this list: his ability to dress in a way that truly reflects his personality, which is vibrant and funny as hell.

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Robert Redford

I genuinely have a hard time deciding when Robert Redford has been the hottest in his life; as a young actor he was absolutely jaw dropping, the kind of man who, if I saw him in line at the grocery store, would make me lose consciousness. But as an older man? He is rugged, handsome beyond belief and puts men half his age to absolute shame. But through the years, one thing about Redford has remained the same: his impeccable sense of style. His earthy aesthetic has transcended his entire career, a kind of hot-professor-meets-Southwestern-cool vibe: field jackets, denim, cozy sweaters, chest hair out, casual button-downs, suede coats. To be fair, there is very little (OK, nothing) that would look bad on Redford. His timeless sense of style means that he always looks sublime.

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Humor. Skill. Wit. Sex appeal. That order. —Robert Redford

Martin Scorsese

Martin Scorsese is best known for bringing iconic gangsters to life on film; the clothing worn by his leading men is a style genre unto itself. Last year I spent some time chatting with longtime Scorsese collaborators costume designers Sandy Powell and Christopher Peterson, who explained that many of the sartorial details in Scorsese films come straight from the source — like the infamous Capo collars seen in many of his films, which are a tribute to collars Scorsese saw growing up. This eye for fashion translates to his personal life as well. Scorsese is your quintessential older Italian man. One of my favorite pictures of him is on his daughter’s Instagram: he’s sitting on her dorm room bed and you can see his dress socks peaking out from under his trousers. Whether he’s accepting an award or chatting with Fran Lebowitz, you can tell he takes pride in everything he wears. His suits look expensive but not pretentious, his shirts are always pressed and luxurious, and he’s not afraid to have a little fun — a Nehru collar shirt here, a patterned jacket there.

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Robert De Niro

If Scorsese is the classic older Italian man, DeNiro is his slightly less traditional counterpart. As a young actor, De Niro’s style radiated sex appeal; he always looked slightly rakish, like he had overslept after a long night of babes and booze. But he always looked damn good: white henleys, rich brown jackets, mid-rise jeans, messy hair. These days, De Niro dresses differently, but he hasn’t lost his charm. He loves a good knit polo paired with a sport coat — a look we have seen over and over on this list, because it simply works.

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John Kerry

John Kerry makes politics look good; as someone who went to college on Beacon Hill in Boston, I was surrounded by men who looked and dressed like Kerry. But he’s the blueprint, and no one really comes close. He always looks crisp but easy, refined but unpretentious. Whether he’s wearing khaki slacks and a brown bomber jacket or slim-cut suits, Kerry is an instant classic.

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Harry Belafonte

Harry Belafonte’s unique style as a young musician is what landed his spot on this list, and his continued sense of classic style is what cemented it. These days Belafonte looks sharp in classic-fit suits and relaxed button-downs; for less formal events, he opts for sweaters and loves a leather bomber. Back in the day, Belafonte’s signature look included mid-rise trousers and a V-neck peasant blouse. Occasionally he’d wear a variation of this — an open button-down and blazer, but a bare chest was never far from sight. The soft sex appeal of this look carried him through this career.

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Sidney Poitier

Sidney Poitier is an acting giant, and his fashion legacy lives up that reputation. As a young man, Poitier kept it simple — perfectly tailored classic-fit suits on the daily, with award-show looks that were unrivaled: tuxedos with tails, white bow ties and double-breasted jackets. These days, Poitier’s style remains refined, understated and impeccably tailored. And he still knows how to rock a tux.

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“Every new fashion is a form of rebellion.” —Sidney Poitier

Jack Nicholson

Jack Nicholson’s sense of style, like the man, is mischievous, natural and completely one-of-a-kind. He dresses well but doesn’t ever really look like he cares to, which makes him even more alluring. Whether he was on the arm of Anjelica Huston or doing press for The Shining, Nicholson looked effortless, from his relaxed, broad collars, button-downs and leather jackets to his wide-lapel suits and signature shades.

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Jay-Z

Few men on this list have undergone the style evolution that Jay-Z has, and fewer could nail every single phase of it the way he has. From his Rocawear days to the perfectly tailored suits he wears to accompany Beyonce to award shows, Jay-Z always looks considered, sharp and singularly cool. Even his casualwear never misses a beat: his slim jeans complement his trim frame, and he pairs them with luxe short-sleeve shirt, logo tees and bold sweatshirts and jackets.

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Tony Bennett

Tony Bennett’s style is definitive for the crooner genre. As an older gent he wears mostly classic-cut suits and separates in rich blues, greys and even black, but he can still pull off subtle and refined patterns like a windowpane when he feels like it. As a young performer, he dressed how you’d imagine the dictionary would define a musician of his generation to look: suave suits, retro knits and shirts, and the occasional fanciful accessory like a scarf in place of a tie.

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Andrea Boccelli

For decades, Andrea Boccelli has been taking Italian fashion and the drama of operatic costuming and adapting it for his performance attire; lush three-piece suits with offset sateen lapels, scarves of varying textures and colors, and monochromatic suits. These days Boccelli opts for slimmer-cut suits; they accentuate his trim physique and keep him looking modern while he performs a centuries-old art. Earlier in his career he loved a classic fit suit or tux and pulled them off with the same ease — this versatility all a testament to his consistently superb tailoring.

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Ian McKellen

Ian McKellen’s style is quintessentially English. But unlike some other icons of his generation (think Michael Caine), McKellen dabbles in looks that are slightly bolder and more playful. He’s not afraid of a bold or colorful patterned suit, and he’s rarely spotted without a vibrant scarf tied loosely around his neck. Even at formal events, McKellen veers left of center, foregoing traditional wool tuxes for velvet ones or a three-button option. Throughout his decades-long career, McKellen has taken many a fashion risk, and they’ve all paid off handsomely, landing him as the final entry on this list.

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