The Best And Worst Dressed Stars Of The '60s

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It's the decade when man landed on the moon, the Cold War was getting ever colder, and fashion changed a ton. That's right, it's the swinging '60s. Sartorially, it was a decade of psychedelic colors, velvet-draped hippies, and mod-ish miniskirts. But what was it about the era that made it so unique style-wise?

"There is a sort of overtly democratic ethos to '60s fashion, there's a sense of mass consumerism ... Fashion in the '60s becomes, I think, a kind of metaphor, a symbol, of wider social changes," said Dominic Sandbrook on the podcast he co-hosts, "The Rest Is History." "So the rise of the teenager, the rise of youth culture. But also the enormous economic recovery from the austerity of the 1940s and the privations of World War II and the development of this sort of new ... full employment and economic growth and consumerism," he explained. "And fashion actually stands in for a lot of that." Indeed, whether it was modern materials like polyester and PVC or an increasingly casual vibe, clothes (and the world writ large) would never look the same again.

So, here are the best and worst dressed stars from the decade of stylistic switch-ups.

Between his leather jackets, uber-cool cardigans, and prim Persol sunglasses, Steve McQueen was, and remains, a style icon. Although you're unlikely to find any trendy '60s loud shirts or bright pants in the "The Great Escape" actor's closet, his clothes had a timelessness in how well they fit and were made. That's something that'll forever be trending.

"Just the coolest man that ever lived," wrote one user on TikTok. Indeed, McQueen is '60s coolness personified.

A '60s John Wayne looked indistinguishable from many of his on-screen personas, and not in a good way. Sartorially, the frequent cowboy cosplayer's on-set and off-set styles were almost identical, whether he was wearing a leather vest to an event or Western-style hats after clocking out. The "Rio Bravo" actor might have developed a signature look, but it doesn't look very '60s or indeed stylish. 

In the decade of mods and rockers, Wayne was still keeping it Western, and that look doesn't get a "yeehaw" from us.

When you think of '60s style, you might think Edie Sedgwick (aka the Factory Girl). The crop-haired fashion icon wore sleek leotards, Beatnik-y striped shirts, and some of the most statement earrings you'll ever see while in the orbit of Andy Warhol's Factory scene. It's a look that's both effortless and perfectly put together.

"It's not that I'm rebelling," Sedgwick herself said of her style (via Grazia). "It's that I'm just trying to find another way." She certainly found a style that was quintessentially her own, and quintessentially '60s.

There's no denying that Jane Fonda is a fashion icon. Heck, we've tracked down the exact clothes Fonda wears on "Grace and Frankie." However, the late 1960s weren't her most impressive years style-wise.

While she became a style icon for her role in the 1968 flick "Barbarella", her off-screen looks from that era were less impressive. Whether it was uninspired multicolored striped jumpers or her shaggy (read: Karen) haircut at the Isle of Wight festival in 1969, it was a rare losing streak in her often winning style.

Like his music, Miles Davis' fashion was always changing in the best way. At times he looked dapper and sharply suited, accessorizing with some statement sunglasses. At other times, he wore gorgeous lace-up double denim, again, with statement sunglasses. That's jazz!

"Clothes are like a beat," Davis himself once said (via JazzTimes). "You gotta fit with what's happening. You can't be out of step and expect people to dig you." In the '60s, there wasn't a bum note in his wardrobe.

"[My suits] are in the middle of fashion," Cary Grant once said (via GQ). "By that I mean they're not self-consciously fashionable or far out, nor are they overly conservative or dated." However, it's an ethos that made his '60s look all a bit too middle-of-the-road.

While Grant's sensible style is by no means bad, it is, as the kids would say, mid, and hardly best-dressed material. As "The Philadelphia Story" actor himself added, "[I]f a man's budget restricts him to only one suit, then I would choose something unobtrusive."

Who was Jane Birkin, the inspiration behind The Birkin Bag? Well, she was one of the best-dressed stars of the '60s, remains a Pinterest darling, and inspired a generation of It-girls. It's a testament to how good her styling sense was because all she often wore was a white T-shirt, jeans, and statement shoes.

But she could also do more than some Levi's 501s and small block heels. Between Birkin's white crocheted wedding dress, risqué black see-through dress she wore in 1969, and pop-collared peacoats, her style was always par excellence.

By the 1960s, Elizabeth Taylor's big dresses and bigger hair looked far less fashionable than they did in the previous decades. Far from a closet revamp in line with youth-focused colors and cuts, instead, the "Cat on a Hot Tin Roof" actor stuck to her old reliable floral patterns and old Hollywood dresses.

But don't just take our word for it. The fearsome fashion critic Richard Blackwell (aka Mr. Blackwell) agreed. According to the Los Angeles Times, he claimed Taylor's 1963 'fits were reminiscent of "the rebirth of the zeppelin."

"I felt I was from outer space," the British supermodel-singer Twiggy said about the 1960s Twiggymania (via Vogue). "Everyone wanted to come and look at me." But we think that the reason people wanted to look at her probably had something to do with her top-tier style.

Whether it was her pioneering androgynous pinstripe suiting or statement shirtdresses, Twiggy changed the game when it came to '60s style. It wasn't just her clothes. Here are the iconic Twiggy hairstyles that people still wear today.

Another famous face on the aforementioned Mr. Blackwell's fashion hit list was Sophia Loren. "[She dresses like] the Italian shop girls she portrays in movies," wrote the clothing commentator (via the Los Angeles Times). Indeed, the "Marriage Italian Style" star's look was kind of costume-coded, with her fur coats, sparkling and patterned dresses, and once, even a swimming cap while at the airport.

She has had some seriously stylish looks over her career. Heck, just look at Loren's stunning transformation. However, the '60s weren't her decade sartorially.

In the '60s, The Rolling Stones' Mick Jagger wore clothes so iconic that they'd be referenced and remembered ad infinitum. Like Twiggy, he adopted an androgynous style that included shirtdresses but also leaned into modern masculinity with slim-fit checked suits.

You only have to look at current stadium pop prince Harry Styles to see Jagger's '60s style legacy. Between wearing ruffled shirts onstage, copying his knitwear in photo shoots, and literally doing Jagger cosplay on "Saturday Night Live," the rocker's '60s looks remain an essential style text for the modern pop boy.

In 2025, Dick Van Dyke became a centenarian. However, the larger-than-life "Mary Poppins" star always dressed like an old man, even in the 1960s.

As Van Dyke's star continued to rise after the release of the aforementioned 1964 film, his style didn't keep up. Instead, Van Dyke would often be seen in either a suit or a shirt with a cardigan. It's not a style that was going to get into Vogue or start any trends, especially in the age of experimental patterns and unorthodox suiting that was the '60s.

Marilyn Monroe has so many iconic '60s looks, it's hard to know where to start. There's the green sequined number she wore at the 1962 Golden Globes, there's the floral coat and bikini combo from "Something's Got to Give," and of course, there's the $12,000 dress she wore to sing "Happy Birthday" to President John F. Kennedy in 1962 (which was later donned by Kim Kardashian).

We can only imagine how many more iconic outfits we would have seen from Monroe if she had been around in the iPhone era.

We can tell why Lucille Ball is better known for her comedy than her style. In the free-love and fun-colored '60s, she looked almost overly prim and proper in her fur-cuffed two-pieces and checkered tops. They were looks that were not dissimilar from a caricature of an evil headmistress in a children's movie. As the aforementioned Mr. Blackwell noted (via Entertainment Weekly), "Lucille Ball seems to bend over backwards to look ridiculous." 

Sadly, when it came to '60s style, Ball didn't seem to know ball.

"Paul Newman is a man who can pull off anything," wrote one TikTok user. So, it's even better that he elevated his style by producing some of the best and most well-remembered looks of the '60s.

His mix of wide-open shirts, big aviator sunglasses, and sharply tailored suits hasn't gone out of style over 50 years later, with 21st-century online content creators attempting to ape Newman's look. However, we're not sure anyone will ever be able to recreate the effortless macho style the actor had.

In the decade of big patterns and psychedelic color combos, Woody Allen's beige blazers, checked shirts, and sand slacks were categorically not in.

The "Annie Hall" director and star essentially dressed like a substitute math teacher, even in television appearances, and that's not the best look in an era when fashion went all experimental. Rather, Allen's looks are safe, conservative, and neutral-toned. It's such a nonexperimental look that it almost goes full circle and becomes avant-garde.

The painter David Hockney's scruffy slim-line pinstriped suits and knitted ties are both classically '60s and totally effortless. "He looked as if he had got out of bed," fashion editor Jeremy Langmead told The Guardian. "[I]t didn't look too contrived, he didn't look in the least self-conscious ... that was how David Hockney looked."

Indeed, Hockney's outfits looked like they'd been through a long shift in the studio, and were all the better for it. Heck, he almost looked as good as the ultra-cool subjects in his paintings.

Speaking of great 20th-century artists, the innovative film director Orson Welles wasn't dressing his best in the '60s. Between his big, very badly tailored suits and a cape he wore in a TV appearance, Welles' sartorial experimentation wasn't quite as good as his experiments on-screen.

That's just clothes from his own closet. Some of the outrageous outfits he wore while in character include going all in as Benjamin Franklin and, while playing a Viking, dressing in a bizarre red hat and robe.

Ronnie Spector and The Ronettes always looked seriously stylish in the '60s. Over the course of the decade, they wore both cool cropped mod-ish suits and glamorous dresses while performing on stage.

"Their unique look and fashion permeated the culture of the 1960s and has transcended generations," as a caption on Spector's official Instagram puts it. "[T]heir flawless makeup is as on-trend today as it was then." There's no doubt about it, baby, we love their style.

No one can deny that Jimi Hendrix had a quintessentially psychedelic '60s style. He's essentially what most people would think of if they were asked to picture a '60s rocker. While he was playing the guitar behind his head or lighting it on fire, the six-string wizard wore eccentric clothing like fringe suede jackets with pink headbands or purple bell-bottoms.

However, the '60s flower power look isn't quite powerful enough to be on trend in the modern world. Indeed, Hendrix's outfits are so hippie, and so '60s, he looks like a parody of himself.

To use parlance from their native Liverpool, The Beatles looked boss and sound as a pound while smashing it style-wise in the '60s. Be it the rocking leather jackets they wore at the start of the decade while in their Hamburg era or the sharp slim suits they donned at the height of Beatlemania, the Fab Four looked fab. Oh, and there's also the classic outfits from that Abbey Road photo.

They had as many stylish eras as any top-level pop star today, and it was all in one decade.

1960s Joan Baez was a fully paid-up flower child, donning beat-up jeans, prayer beads, and, well, no shoes. But there's a fine line between a hippie and a badly dressed musician, and that was a line that Baez frequently crossed in the '60s.

As one X user put it, "a lot of [hippie fashion] in the late 60s can be almost solely attributed to [Baez]." Yet, that doesn't necessarily mean she dressed well. To make matters worse, she had one of the biggest celebrity scandals that completely rocked the 1960s.

To this day, people still want to recreate Holly Golightly's hair from "Breakfast at Tiffany's." But that's just one of the many perma-chic looks Audrey Hepburn turned out in the '60s. It wasn't just diamond necklaces, big sunglasses, and little black dresses. Hepburn had other fab, and equally sleek, looks, from the baby pink gown she wore to the '65 Oscars to a double-breasted suit.

To quote Hepburn (via Vogue), "Some people dream of having a big swimming pool, with me it's closets." Boy, was it some dreamy closet she had.

We know that suggesting Cher is anything less than a fashion icon is sartorial blasphemy. Just look at Cher's most iconic '80s outfits. However, the singer was still working her sense of chic out in the '60s.

Back then, Cher was in a musical duo with her then-husband Sonny Bono, and they wore some pretty out-there (read: bad) outfits. From horrifically colored suits to bright yellow tops with fur waistcoats, Cher wasn't yet quite the iconic dresser she'd later become.

Whether it was turtleneck jumpers and leather jackets or Breton tops, the modern artist Andy Warhol had a '60s uniform that became his signature look. That's the power of his simple, yet incredibly effective, go-to garments.

"Artists aren't supposed to dress up and I'll never look right anyway," says Warhol in the book "Holy Terror" (via The Rake). He shouldn't have been so harsh on himself; we think he looked just right. In any picture from the decade, his dress sense exudes an effortless cool.

While The Who helped start the mod movement across the pond, which was characterized by Union Jack jackets and cool tees, their late-'60s onstage looks weren't so impressive. Rather than keep the perpetually stylish mod aesthetic, the "Baba O'Riley" hitmakers evolved into velvet blazers or tasseled vest-and-trousers combos or even outrageous ponchos.

Frontman Roger Daltrey's look at 1969's Woodstock sums it up, as he wore a jacket with perhaps the longest tassels we've ever seen while forgoing a shirt. We wish they'd stuck with their sleeker looks from earlier in the decade.

The "Belle de Jour" star Catherine Deneuve was also a Yves Saint Laurent muse, after she met the designer in 1965 to request a dress for a meeting with Queen Elizabeth. Thankfully, there was no fashion house more stylish in the '60s than YSL. 

She wore so much YSL, from masculine tuxedos to pretty peacoats to long flowing dresses, and in every look she stunned. As Deneuve herself put it (via the BBC), "They are the creations of a man who was so talented and who only created to make women more beautiful."

In the '60s, the singer Connie Francis wore a lot of bright colors and big flowing dresses. Although these looks include both patterns and prints, they don't have the let-your-hair-down cool that the decade was characterized by. Instead, you would be forgiven for thinking some of her '60s 'fits were actually looks taken from the more classically clothed '50s.

Francis was an innovative trailblazer in the music industry, but sadly the same can't be said about her outfits.