One's 20s are a strange time for most people. While some may be married with kids, others may still be in school, getting ready to pursue the career of their dreams. Either way, that's just the case for us regular folks.
For most stars, their 20s are a whole other phase of going under the spotlight, growing a fan base, making millions, and most, of all, setting trends. Looking back at celebrities' snaps from when they were in their 20s is much less embarrassing than looking back at ours. Therefore, let's cut to the chase and look at 40 famous figures, then vs. now.
Reese Witherspoon
It doesn't matter if it's today, last year, or two decades ago, Reese Witherspoon has always been a beautiful woman looked up to by many of her fans. Today, she is more active as a producer, with many new works, including The Dry, Pyros, and The Cactus coming up.
Known for films like Legally Blonde and Sweet Home Alabama, Witherspoon's style has hardly changed since her 20s. Take her makeup, for example. Witherspoon was and still is a fan of a minimalistic approach to beauty. Be honest—how often do you see her with bold red lips and a heavy smokey eye? Almost never!
Janet Jackson
Janet Jackson is a singer, actress, and dancer from the Jackson family of entertainers. Yes, she is the sister of the legend that was Michael Jackson. Having started as part of The Jackson 5, she went on to make a name for herself through hit songs like Miss You Much, Escapade, and That's The Way Love Goes.
The 54-year-old sure knows how to keep up with the ever-evolving fashion world. However, there's one thing that'll always stand out—her love for the color black. Have you noticed that she's hardly seen wearing any other color? Well, you will now! Other than her 2019 tours, Jackson hasn't been very active lately.
Jennifer Aniston
With her role as Rachel Green on the famous sitcom Friends, Jennifer Aniston caught the world's attention. Her beauty, paired with her exceptional acting skills, is what keeps Aniston going with no shortage of work. In fact, she starred in Murder Mystery in 2019 and will play Denise White in Hail Mary soon.
Aniston, now 51 years old, has been a conversation topic lately, given how flawlessly she's aged. Not only that, but her fans can't help but be awed at her well-balanced sense of fashion. When necessary, Aniston can rock the most ethereal dresses but sticks to jeans or khakis for everyday wear.
Gabrielle Union
From Deliver Us from Eva to Something the Lord Made to Being Mary Jane, Gabrielle Union has starred in various films and television series that have earned her multiple award nominations. She has been starring in L.A.'s Finest since 2019 and will soon appear in White Dave and The Perfect Find.
With her wispy hair and beautiful smile, Union easily stands out in a crowd. The melanin-kissed beauty is never one to back down from sporting clothes with luminously vibrant colors. Her tastes have sure changed from when she was 20, but we're all for it. Union even has a fashion line with New York & Company, as per GH.
Madonna
If you have known Madonna through the decades, then you know she has never been one to worry about being the odd one out, particularly when it comes to her fashion sense. In fact, this unique fashion sense may have contributed to her achieving world-wide fame as a singer.
You may recall her multi-colored hair in the '80s. While it may not be so now, her fashion style is hard to keep up with. Love to Know describes it as being punk, androgynous, hip-hop, geisha, and much more. Now aged 62, Madonna's early songs like La Isla Bonita, Vogue, and Into the Groove are still popular today.
Diana Ross
The Supremes' lead vocalist Diana Ross's voice is literally music to our ears. She may no longer be as active as she used to be, but that doesn't stop her from being one of the best musicians of all-time. Even after embarking on a solo career, Ross touched the stars with top-charting singles such as Ain't No Mountain High Enough and Love Hangover.
When it comes to Ross's fashion tastes, she tends to weigh towards a feminine approach. Nevertheless, the 76-year-old can still put on a show with her Afro and glamorous outfits. In 2020, she released a compilation album, Supertonic: Mixes.
Gisele Bündchen
It didn't take Gisele Bündchen long after launching her career to become one of the world's highest-paid supermodels. Her $400 million fortune will vouch for that. The 40-year-old has modeled for brands like Chloé and Versace and appeared on covers of Vogue and Rolling Stone, among others.
Bündchen's style is super edgy, which is no surprise given that she's a model. However, if you spot her on the streets on a normal day, chances are she'd be wearing jeans and boots. Even today, Bündchen can rock a pair of bell-bottoms like it's the '70s! Somehow, her blonde hair has remained just as luscious throughout the decades.
Kim Kardashian
Wherever she goes, Kim Kardashian presents herself in such a manner that all eyes will be on her. She is so prominent in pop culture that even haters will stalk her social media to get a glimpse of her steamy fashion sense. Learn from the best, if you must.
Kim is widely known for starring on E!'s reality series Keeping Up with the Kardashians alongside her family. At present, she is a mother of four and is also the founder of both KKW Beauty and fragrance lines. In 2020, Kim will appear in Marry Me and provide her voice for PAW Patrol: The Movie.
Beyoncé
Queen Bey could never go wrong with fashion, from funky denim jeans, bandanas, and large hoop earrings to high-waisted skirts and crop tops to sheer yet elegant red carpet dresses. Even if she did, it would most likely become the latest trend. How times have changed from her no-makeup makeup days to her current full-on glam looks.
Beyoncé is a world-famous singer. The 39-year-old best-selling artist is famous for songs like Beautiful Liar, Single Ladies (Put a Ring on It), and Halo, among others. Her latest single, Brown Skin Girl, featured her firstborn, Blue Ivy.
Bob Dylan
What Bob Dylan has done in the music industry isn't the only extraordinary thing. His fashion sense that grabbed attention in the '60s also remains unmatched. More often than not, his early photos will show him wearing leather jackets, sunnies, and even hats (still a go-to).
Now aged 79, Dylan has been an icon in pop culture for over five decades. He has made heaps of contributions to the music industry with songs like Blowin' in the Wind, The Times They Are a-Changin', and Like a Rolling Stone becoming only a few of many hit songs. Dylan released his 39th studio album, Rough and Rowdy Ways, in 2020.
Kate Middleton
Kate Middleton's outfits since becoming the Duchess of Cambridge may be all classy and elegant, but back in her 20s, she too was like any other youngster. Everything from spaghetti-strapped tops to jeans to shorts was in her wardrobe.
Even today, the 38-year-old has a serious impact on the British and American fashion industries—a trend the media likes to call the "Kate Effect." Middleton met Prince Williams when they were both students at the University of St. Andrews. The two began their romantic involvement in 2003, ended up at the altar eight years later, and share three children now.
Eva Longoria
A woman of all seasons, Eva Longoria is an American actress, filmmaker, restaurant owner, activist, and businesswoman. She rose to prominence with her portrayal of Isabella Braña on CBS's The Young and the Restless and made her fame permanent playing Gabrielle Solis on Desperate Housewives.
Like most celebrities, Longoria likes to fashion unique dress designs at red carpet events. However, every other day, the 45-year-old likes to keep things casual with jeans, shirts/tops, handbags, and sunglasses. Like most of us, but somehow better. In 2020, Longoria appeared in Sylvie's Love, Flipped, and even completed the upcoming film All-Star Weekend.
Leonardo DiCaprio
With films grossing over $7.2 billion worldwide, it's safe to say that 45-year-old Leonardo DiCaprio is up there among the best actors in the world. DiCaprio can bring to life characters of any caliber, and yet, he is best known for playing Jack Dawson on the blockbuster Titanic. His other best works include The Aviator, The Revenant, and Once Upon a Time in Hollywood.
According to IMDb, it's just been announced that he will play Theodore Roosevelt in the upcoming film Roosevelt. In men's fashion, DiCaprio is an inspiration, showing his love for branded pieces, which he sure can afford.
Robin Wright
Describing Robin Wright's sense of fashion is no easy task as she is so unpredictable. One day, it might be skinny jeans and a sweatshirt, whereas, on another day, she could go chic with a white blazer and pants combination. The 54-year-old certainly has a thing for monochromatic tones.
As an actress and director, Wright has a long list of credits to her name. She first gained attention from the soap Santa Barbara; meanwhile, her breakthrough on the big screen came with The Princess Bride. Forrest Gump and Wonder Woman are only a few of her other noteworthy projects. Wright's upcoming works include Wonder Woman 1984 and Zack Snyder's Justice League.
Katie Holmes
Katie Holmes couldn't have walked beside a man like Tom Cruise without knowing everything there is to know about fashion and beauty. Lately, she has been into a fusion of youthful and flirtatious looks, which we are all down for. In her 20s, Holmes was as simplistic as she could be.
After first rising to fame as Joey Potter on Dawson's Creek, Holmes went on to broaden the scope of her film and television participation with roles in Batman Begins, Pieces of April, Woman in Gold, and so on. Today, Holmes has a teenage daughter, who will probably soon look like her younger self in the photo above.
Meghan Markle
When Meghan Markle was an actress, Americans looked up to her ensembles. This was especially the case among working women who'd take Markle's (more like Rachel Zane's) officewear on her famous role on Suits as an exemplar. For a moment there, we thought her days of casual vibing was gone when she married Prince Harry and became Duchess of Sussex.
However, since they stepped down from their royal duties and moved to America, life, as they knew it in the palace, was over. It came to light in September 2020 that Prince Harry and Markle signed a deal with Netflix to reportedly develop scripted and unscripted new projects.
Heidi Klum
Is it just us, or does Heidi Klum look very different in her 20s picture compared to today? The German-American model was only a teenager when she received a $300K contract from Metropolitan Models New York. Of course, she accepted, and her life took a major turn from there.
A former Victoria's Secret Angel, Klum has reached the greatest heights in the modeling industry while also securing her fair share of television hosting/judging credits. A few years ago, the 47-year-old told Elle that her style was "fearless," and we couldn't agree more. The mother of four is a true fashionista if you will.
George Clooney
If the photo above didn't show George Clooney with his wavy hair, was it even taken in the '80s? Nothing screams the '80s more than the mullet. Especially not for men! Luckily for Clooney, he hasn't lost a bit of his stylish charm even at his current age of 59.
The award-winning American actor and filmmaker shot to glory with his portrayal of Dr. Doug Ross on the '90s series ER. His credits since then total over 90, with the newest role in The Midnight Sky coming up. He is married to the stunner Amal Clooney, with whom he often coordinates outfits.
Kate Beckinsale
Showing off her pale white skin with a deep red lipstick shade may just have been Kate Beckinsale's most iconic look in the '90s. That's not so much the case today. While the 47-year-old certainly knows her way with makeup, she often sends out casual vibes with her apparel.
Now a successful actress and model, Beckinsale attended the University of Oxford in her younger years. Her childhood dream of becoming an actress has come true now. Beckinsale made a transition to Hollywood gradually after establishing herself in British cinema with films like Emma and Alice through the Looking Glass. She will soon star in Jolt and El Tonto.
Julia Roberts
Julia Roberts is a renowned actress who became a leading lady after successfully portraying the lead role in Pretty Woman. She is, indeed, the prettiest of pretty women. Her subsequent hits were Steel Magnolias, Runaway Bride, and Erin Brokovich, among numerous others. Among the many prizes in her trophy cabinet is an Oscar and three Golden Globes.
Now aged 52, Roberts is a fashion icon who can match just about any outfit with her radiant smile. While her red carpet dresses are nothing short of simple glamor, Roberts can push boundaries when it comes to everyday wear. Fans can look forward to her upcoming projects: Little Bee and Gaslit.
Denzel Washington
Denzel Washington is with no question a prolific actor who has made a mark in Hollywood for his wise choice of characters. His roles are usually defined by traits like humanity, dignity, and inner strength. A two-time Oscar-winning actor, Washington is best known for such films as Cry Freedom, Malcolm X, Inside Man, and The Equalizer films.
While 2019 and 2020 have been quiet years with acting, he will star in The Little Things and The Tragedy of Macbeth in the coming years. When it comes to his style, Washington hasn't changed much since the '80s, when a shirt, slacks, and a tie is all he needed.
Courteney Cox
We're not saying that Jennifer Aniston was overrated, but Courteney Cox was certainly an underrated one on the Friends cast. Since achieving widespread success through her role as Monica Geller on the show, Cox has had a successful career with other notable appearances as Gale Weathers in the Scream films and Jules Cobb in Cougar Town.
Today, Cox's style is tasteful, yet not overly sophisticated, which is the perfect amount we can expect from her. However, her '90s attire, particularly the looks on Friends, are still recreated by stylists and fashion bloggers in the present. Soon, Cox will reprise her role in Scream for its fifth movie.
Amy Adams
Whether it's a comedic role or a dramatic one, filmmakers can rely on Amy Adams to make them come to life in ways better than they could've imagined. In years like 2014, 2016, and 2017, she was among Forbes' list of highest-paid actresses in the world. Now 46, Adams is best remembered for roles in Drop Dead Gorgeous, The Fighter, and Arrival, among others.
Later in 2020, Adams will star in the Hillbilly Elegy while working on new productions like The Woman in the Window. She may be known for her jaw-dropping red carpet looks now, but her eye for good fashion wasn't an overnight development but rather a knack.
Jessica Alba
Looking at this photo of Jessica Alba, we can't help but wonder if she inspired the high school blue eye wave in the '00s. Either way, the Dark Angel star perfected this fun little look, just like she did (and still does) many others.
Known for her chic style, Alba is now a 39-year-old known for not only her acting but also her consumer goods company named The Honest Company. Since starring in box office successes like Fantastic Four, Valentine's Day, and Little Fockers, Alba hardly had a shortage of work. She currently plays Nancy McKenna on L.A.'s Finest.
Keanu Reeves
Keanu Reeves captured the hearts of millions of fans worldwide in no time, particularly due to his humbleness and charm. The Lebanon-born Canadian actor launched his career in the mid-'80s but didn't quite earn stardom until he played Ted Logan on Bill & Ted's Excellent Adventure.
Reeves' films only started to become major successes after several box office flops. Some of his other notable roles were in The Devil's Advocate and The Matrix films. Soon, you can see him in the latter's fourth movie. Besides his beard, not much of the 56-year-old's choice of appearance and style has changed compared to his 20s.
Serena Williams
Serena Williams may have muscles more toned than the average woman, but that doesn't mean she doesn't like dressing up. In fact, the 39-year-old tennis superstar has a fantastic taste in fashion that can often be on edge. Her wardrobe is far from being all activewear.
Williams is a former World No. 1, whose current rankings have dropped to tenth. She has secured 23 Grand Slam titles, which is the highest recorded by any Open Era player. Her career has allowed her to make a $200 million fortune. Since 2017, Williams has been married to Reddit co-founder Alexis Ohanian, with whom she now shares a daughter.
Cindy Crawford
Back in the '80s, Cindy Crawford was one of the most popular supermodels in existence. Fast-forward over three decades, and nothing much has changed—neither with her looks nor with her status. Being a cross-generational fashion icon, many women look up to Crawford to set the bar for current trends.
In addition to her modeling career, which saw her appear in hundreds of magazine covers and brands, the 54-year-old has also accepted the occasional film and television roles. The latest voice appearance was in Bojack Horseman in 2019. Crawford may have retired from full-time modeling, but her effortless yet chic style is still up-to-date.
Naomi Campbell
With her long and shiny hair, beautiful skin tone, and fashionable outfits, Naomi Campbell rocked the runways in the '90s. Despite being affected by racism, Campbell thrived and became an international success in her 20s. Having modeled for famous magazine covers like Vogue and British GQ and walked for designers like Gianni Versace, Campbell's success only rose and continues to grow.
Her steamy appearance, paired with her flamboyant style, makes it that much harder to believe that she is now 50 years old. In 2020, Campbell appeared as herself in the film Black Is King and reality series Making the Cut.
Halle Berry
Halle Berry is another melanin-kissed goddess who has left the world in awe with her stunning looks. Berry, now aged 54, is widely talked about for her beauty, which some might even describe as "aging backward." You can't expect anything less from a Miss USA runner-up and Miss World contestant.
Berry works hard to keep her figure on fire (hypothetically) and doesn't fail to flaunt it in her figure-hugging choice of clothes. For her role in Monster's Ball, Berry won an Oscar that'll go down in history as she is the first woman of color to have secured it. Soon, she'll star in Bruised.
Brad Pitt
If there's anyone better than a young Leonardo DiCaprio, it's the '90s version of Brad Pitt. He is one of the most popular men's fashion icons in existence and is quite the trendsetter nowadays—even more so than his younger self was. Does anything beat Pitt in a tuxedo, though?
The 56-year-old was married to two of the most exquisite beauties in Hollywood: Jennifer Aniston and Angelina Jolie. He is an actor and producer known for films like Fight Club, Ocean's Eleven, and World War Z. It looks like Pitt has his hands full in the coming years as he gets ready to work in Blonde, The Underground Railroad, and Americanah.
Winona Ryder
Looking at Winona Ryder now, it's hard even to process that she had her hair cut super short back in the day. But then again, this was around the same time that she opted for the gothic/grunge looks, which sure made her a style icon at the time. Today, Ryder's tastes may have changed, but her love for the color black seems to be unshaken.
From Beetlejuice to Edward Scissorhands to The Age of Innocence to Little Women, Ryder has shown off her acting skills in many major hits. As of 2016, the 47-year-old has been starring as Joyce Byers in Stranger Things.
Johnny Depp
In every Johnny Depp movie, we'd see him with a selection of clothes so uniquely appealing to the character. May it be Jack Sparrow on Pirates of the Caribbean, the title character on Edward Scissorhands, or even Willy Wonka on Charlie and the Chocolate Factory. In recent years, he has gone to portray Gellert Grindelwald in the Fantastic Beasts films.
Today, the 57-year-old Depp is a sucker for semi-formal wear and is often spotted with Lemtosh style or aviator sunglasses. In the '80s, Depp seems to have been much more laid back in style, with his go-to choice being T-shirts and sweatshirts.
Harrison Ford
The photo of Harrison Ford may be monochromatic, but you can still tell what a charmer he was. He may have been a pioneer of the smart casual men's wear trend, which has even continued into the 21st century. In Vogue's opinion, Ford's style hasn't changed much over the years but somehow feels just up to date. We can't agree more!
Still looking as sturdy as he can be at 78, Ford is a prosperous actor whose films have grossed nearly $10 billion worldwide. His greatest portrayals include Han Solo on Star Wars and the titular character in the Indiana Jones films, of which the fifth movie is coming up.
Jack Nicholson
Jack Nicholson may not have officially retired yet, but he hasn't played any significant roles for a decade. Although we miss seeing him on the screens, we cannot complain, seeing as he is 83 years old. Known for films like Chinatown, Batman, and The Departed, Nicholson has secured numerous accolades through the years, including three Academy Awards.
On his days off (which he has been having a lot of lately), Nicholson lives his life seeing the world through a polarized lens. His sunnies are one of the main parts of his ensemble. Although not as much, it was still a favorite in the '60s.
Robert De Niro
If only our favorite stars stopped aging. Since that's far from the case, Robert De Niro doesn't look anywhere close to what he does in this photo anymore. Well, it has been over five decades since this photo, and sure, he has wrinkles now, but his sense of fashion is still intact.
Still handsome as ever, De Niro must have a massive collection of suits and ties as it's his go-to choice of clothing. The 77-year-old achieved stardom with his role in The Godfather Part II and had other prominent roles in Taxi Driver and The Irishman. Later in 2020, he will star in The Comeback Trail.
Cher
From her makeup to her costume choices, Cher likes to do everything in her power to stand out. Well, we're not complaining because the diva has triggered various fashion trends over the years. Even at her current age of 74, Cher screams flamboyance and vibrance.
The "Goddess of Pop" first came to attention in the '60s as part of the husband-wife duo, Sonny & Cher. She later found triumph as a soloist with top-charting singles like Gypsy, Tramps & Thieves, and Dark Lady. Cher has also maintained a successful acting career, which shot back to the spotlight in 2018 with her role on Mamma Mia! Here We Go Again.
Victor Garber
Victor Garber first started his acting career in theatre. Even though he had a brief career as a folk singer before that, it didn't quite see the success he saw as an actor. Garber is widely recognized for his roles in Sleepless in Seattle, The First Wives Club, and Legally Blonde.
Today, Garber is 71 years old and still looks as charming as he did in his 20s. Apart from selecting tuxedos and suits for red carpet events, Garber likes to keep things very casual and chill for everyday wear. He is set to appear in Happiest Season and voice a character in The Gettysburg Address soon.
Tom Hanks
Like in his 20s, Tom Hanks is still super stylish but somehow manages to keep things "age-appropriate." Back in the day, he had a head full of bushy hair that took the '80s vibe up a notch. However, his mane seems to have thinned up, unlike his taste in fashion.
Now aged 64, Hanks is best known for playing the leads in such films as Forrest Gump, Apollo 13, and Cast Away. In 2020, Hanks, too, was among the millions of people infected by the coronavirus. He beat the virus and is currently working on new films like News of the World, BIOS, and Elvis.
Meryl Streep
Yes, Meryl Streep was and still is photogenic, but that's not the only thing that made her '70s snaps perfect. Her naturally ashy-colored hair, charming smile, and her era-friendly clothing choices were all triggers of her success back then. In the present, however, she doesn't think twice about wearing colors and following the latest trends, despite being 71.
Streep is often dubbed as the best actress of her generation, and her record 21 Oscar nominations can vouch for that. Her biggest hits are Sophie's Choice, The Devil Wears Prada, and The Iron Lady. Her fans can await her newest films: The Prom and Let Them All Talk.
Robert Downey Jr.
Since Robert Downey Jr. was considered a part of the "Brat Pack" in the 80s, he naturalized as a teen idol. This not only means that he had many fans, but they also followed his fashion choices. Well, he is now in his mid-50s, and not much has changed, especially considering he is one of Marvel fans' favorite superheroes, Iron Man.
Downey Jr.'s tastes seem to be up to the minute. His choice of clothing, regardless of the function, seems to be a tuxedo. Downey Jr. will star in the upcoming projects: Black Widow, All-Star Weekend, and What If...? (voice).