The Best And Worst Dressed Stars Of The '80s

Fashion sure was something in the 1980s. Remember what it felt like to raid your parents' closet as a kid and try on every single item of clothing that they wore, usually at the same time? Style trends in the '80s resembled something along those lines. If there's one simple phrase to describe fashion at the time, it's that more was definitely more: The patterns were big, the colors were bold, the accessories were overloaded, and the shoulder pads were high. Don't forget about the leg warmers, leather jackets, and the teased-to-high-heaven hair, either.

Considering how many influential faces were part of the '80s, trying to narrow down the best and worst dressed celebrities of the decade isn't as easy a feat as it may sound. We're going to take our best shot at it, though; while it would be incredibly easy to let other decades influence this list, we're laser-focused on what was presented between 1980 and 1989. Talent and critical success aside, here's who put their best fashion foot forward — and who should've received some extra help.

There should've been no doubt that "The King of Pop" would be on this list, so let's just get him out of the way. Michael Jackson delivered so many iconic moments throughout his career that it would take all day to get through them. As far as style goes, Jackson presented one of the most iconic red carpet looks of the 1980s at the 1984 Grammy Awards: a dark blue sequined military-esque blazer with gold accents, a crystallized glove, and aviator sunglasses. Talk about absolute perfection. 

Cyndi Lauper has always been one of those artists with endless amounts of individualism and self-expression. In the 1980s, her colorful style and massive love of accessories helped her immediately stand out from the crowd, whether on film or in person. More often than not, though, the final result looked more tacky than inspiring. This outfit that the "Girls Just Wanna Have Fun" singer wore for the 1985 Grammy Awards remains a good example: the mismatched fabrics, abundance of accessories, and heavy makeup were a sight for sore eyes, as the saying goes.

Michael Jackson was arguably the most famous celebrity in the 1980s, although Prince wasn't too far behind in popularity. Anyone remember how Cheryl Blossom claimed she invented red on that episode of "Riverdale"? Prince may not have created purple, but his stunning "Purple Rain" outfits sure made their mark on fashion, both in the '80s and beyond. The different shades never seemed to clash with one another; the amount of frills never felt over the top, and the shoulder pads were just the right height for dramatic flair. 

Cher has always been that girl, especially when it comes to fashion. Name a better long-term collaboration than Cher and designer Bob Mackie: We'll wait. One of the most daring outfits worn by Cher in the 1980s, designed by Mackie, of course, was this sheer black gown covered in rhinestones and fringe for the 1988 Academy Awards. Cher didn't just win best actress that night (for "Moonstruck"), but she also proved that she had it all: a good sense of style, unmatched confidence, and a seemingly great workout regimen. 

Fans of reality TV may recognize Boy George from all his appearances on "The Real Housewives of Beverly Hills," but in the 1980s, he made some big moves as Culture Club's lead singer. Looking back through photos, Boy George and Cyndi Lauper had a similar thing going on fashion-wise: bold colors, bright patterns, as many accessories as possible, and heavy makeup were the go-tos. As evidenced by this concert photo from 1984, however, the "Do You Really Want to Hurt Me?" singer didn't rock the busy look any better. 

David Bowie proved how fashion-forward he was in the 1970s, especially when he created and performed as the characters Ziggy Stardust/Aladdin Sane, Halloween Jack, and the Thin White Duke. Bowie's keen eye for fashion, coupled with his ability to rock everything he put on, naturally carried over into the 1980s. This blue and gold outfit from one of Bowie's many '80s performances is one of many well-dressed moments from him: You'd think an open chest with ruffles would look silly, but the contrast actually leaves an eye-catching impression.

Grace Jones was the pinnacle of a triple threat in the 1980s. Modeling, acting, singing: The "Nightclubbing" entertainer did it all and then some, with her androgynous features and bold take on fashion a sight to behold each and every time she stepped out. Clothes didn't wear Jones: Jones wore everything she put on with such confidence that even the strangest things looked majestic. For the 1983 Grammy Awards, Jones donned a particularly memorable outfit with incredible ease: a sculpted black leather ensemble designed by Issey Miyake. 

Brooke Shields was a highly sought-after actor and model by the time the 1980s rolled around. This was something extraordinary, albeit later controversial, for someone born in 1965 (Michael Jackson, Shields' close friend, could relate). When styled for an on-screen or off-screen job, Shields looked amazing. At public events and out on the town, however, Shields' fashion choices didn't hold up. This jean set from 1985 with a bright yellow shirt underneath gave contrast, for instance, but came off rather dull for someone who could probably rock a paper bag.

Madonna has popularized plenty of fashion trends over the years, so her inclusion as one of the best-dressed 1980s stars should come as no surprise. Everyone can agree that Madonna's 1984 "Like a Virgin" dress for the MTV Video Music Awards was a cultural reset, but her sense of style extended beyond performance. Take this casual shot of Madonna from 1985 as an example: In this instance, she accessorized just enough, with the right amount of contrast around the neckline, to look effortlessly chic without going overboard.

Freddie Mercury was a revolutionary musician, not to mention person, throughout the 1970s and '80s. With his insane vocals and eye-popping outfits, Mercury was over the top in the best way: His sense of style boosted his artistry in a smart way, not a gaudy one. This particular outfit from one of Queen's many tours provides a solid example of what we mean: The bright yellow shade stood out, as did the jacket's huge straps, just enough to capture a positive stream of attention (as if Mercury didn't get enough of it). 

Because everyone remembers Whitney Houston as one '80s star who met a tragically strange fate, her sense of style during the decade has flown under the radar. Now, Houston had some great fashion moments in the '90s: her 1991 Super Bowl XXV and 1994 Grammy Awards looks come to mind. The "I Wanna Dance With Somebody" singer also pulled off some great designs in the 2000s. In the '80s, however, Houston's outfits were too plain and boring for someone of her caliber, such as this dark, slightly oversized getup from 1987. 

Ozzy Osbourne lived an extremely interesting life, to say the least. In the 1980s, Osbourne finally went solo after a decade with Black Sabbath — and like his personal life, his style was extravagant, flashy, and quite busy. This particular look from 1986 remains a testament to the "Crazy Train" singer's good eye for fashion: the colorful bedazzling and different patterns complemented each other greatly, especially under all the bright stage lights.

Daryl Hannah's stunning transformation took off in the 1980s, especially after she starred in Ridley Scott's "Blade Runner." For a relative Hollywood newcomer, Hannah's sense of style highlighted her natural "wow" factor nearly every single time she was photographed. For the 1988 Academy Awards, as one memorable example, Hannah turned up in a beautiful silver beaded gown that complemented her wonderfully. The sunglasses, shawl, gloves, and flower tied the look together flawlessly, and her platinum blond hair was the perfect cherry on top.

Something interesting to note about Demi Moore, a core member of the "Brat Pack in the 1980s, is that all her publicity photos from the decade were stunning. At public events, however, Moore's outfits left a lot to be desired. An infamous fashion fail occurred at the 1989 Academy Awards, an interesting juxtaposition from Daryl Hannah the previous year: the  attended the event in an out-of-place, self-made ensemble that looked OK on top, yet featured ill-matching black bike shorts on the bottom.

Paula Abdul transformed from a Los Angeles Lakers cheerleader into an all-out superstar in the 1980s, a testament to her natural star quality. As a singer, dancer, actor, choreographer, and future "American Idol" judge, Abdul proved that there's nothing she couldn't do in the '80s and beyond. However, her sense of style didn't back that up. Take her appearance at the 31st Grammy Awards in 1989 as an example: Abdul's dress hit all the fashion hallmarks of the time, but took away from her natural beauty instead of enhancing it.

Before there was Harry Styles and his onstage fashion, there was Mick Jagger. By the end of the 1980s, Jagger remained a core member of the Rolling Stones, but also had a full-fledged solo career. No matter where he was or who he performed with, there was no doubt that Jagger used every opportunity to push the fashion boundaries. This look from a 1989 performance is one of those "simplicity is key" moments that the '80s struggled with: The ruffled pink shirt contrasted wonderfully with the studded black pants. 

Diana, Princess of Wales, gobsmacked the world when she stepped out in her famous black "revenge dress" in 1994. While Princess Diana became famous worldwide as the newest British royal in the 1980s, she quickly gained prominence as a complete fashion icon with virtually no misses. There are so many looks we can highlight, but this underrated monochromatic look from 1989 is one of the more underrated. The shoulder pads? Perfect height. The buttons? Great symmetry. The shade of red? Simply stunning.

Jane Fonda will always be a legend, especially when we look at what living Hollywood icons looked like in the 1970s. Have you ever tried to complete one of Fonda's classic workouts? If so, you may be entitled to financial compensation. It's hard not to love Fonda — but it is hard to like her style in the '80s. Because she was in her fitness era, bright, sparkly leotards with matching accessories dominated her public wardrobe. Compared to everything else Fonda has rocked over the years, however, these bodysuits just didn't hit the right beat. 

Oprah Winfrey's career transformed phenomenally in the 1980s in a now-classic "rags to riches" story: She starred in "The Color Purple" in 1985 and debuted "The Oprah Winfrey Show" in 1986. Winfrey's talent, natural charisma, and influence have been unmatched for decades, yet more often than not, her '80s looks completely missed the mark. This fashion fail from 1989 remains a particular standout: The gold shirt and black dress hardly worked together, especially paired with silver jewelry. It all made Winfrey look frumpy, not fabulous. 

There's no other way to say it: Billy Idol was a cool guy in the 1980s (and still is today, even in his 70s). During that time, Idol left the band that made him famous, Generation X, and became even more famous with a solo career. The "White Wedding" singer's aesthetic may have been extremely predictable — spiky hair, black garments, overlayered accessories, lots of leather — but every outfit was always fierce and somehow felt new each time. This expressive portrait from 1984, for example, gets an A+ for being absolutely awesome.

Sarah Jessica Parker's career took off in the 1980s after appearances in classic movies like "Footloose" and "Girls Just Want to Have Fun," as well as her high-profile relationship with Robert Downey Jr. Although she's known for her long honey-blond hair now, she rocked her natural curls in the '80s. Parker's hair? Stunning. Her outfits? All things considered, not so much. This gray dress and hat combo, for example, gave perhaps "Little House on the Prairie" vibes more than "future Hollywood superstar."

People couldn't go anywhere in the 1980s without seeing or hearing something about Molly Ringwald. With hits like "Pretty in Pink" and "The Breakfast Club," Ringwald was the face of coming-of-age movies. While her acting was celebrated, her fashion choices when not in character didn't hold a candle to her talent. Ringwald's dark gray sweater in this portrait from 1985 serves as a good example of how blandly she was styled. The black hat could've worked with a different outfit, yet it helped instantly age her instead.

Diana Ross has long been an icon and a legend. This rang particularly true for "The Queen of Motown" in the 1980s: By that time, Ross had cultivated an insane amount of success with The Supremes, in her solo career, and as an actor. Like her voice, Ross's looks have always been bold, perfectly tailored, and fabulous. This sequined purple bodysuit from a performance in 1983 checked all these boxes, and then some. 

As far as celebrity comebacks are concerned, Steven Tyler (and Aerosmith as a whole) underwent one of the greatest transformations in the 1980s. Tyler has always been known for his unique voice and sense of style, especially onstage: When in doubt, one can expect Tyler to wear something colorful, flamboyant, and full of character. This portrait of Tyler from 1986 is a hallmark example of how naturally he rocked outfits that looked like they should've never been put together in the first place. 

A lot happened to Milli Vanilli after their lip-syncing controversy made waves in the late 1980s. In terms of their look that decade, Fab Morvan and Rob Pilatus had some fashion-forward moments (like their colorful jackets at the 1990 Grammy Awards), but missed the mark more than they set any sort of bar in the '80s. Let's highlight this look from an ice cream event in late 1989 as an example: Morvan looked rather plain in a slightly oversized tan jacket, while Pilatus' dark ensemble came off muted and out of place.