Then and Now: What Were Today’s Fashion Icons Wearing in 1999?

Twenty years ago—as millennium festivities kicked off around the world—the year’s most fashionable icons hit red carpets in quintessential ‘90s garb. Baggy jeans, biker jackets and retro windbreakers (yes, we remember) ruled streetwear, and runway designs reflected those looser silhouettes.

Many of the celebs dominating the fashion scene today have had remarkable careers spanning 20 years or more. Their looks, just like their careers, have evolved with age. But as the saying goes, history repeats itself—and ‘90s fashion has made somewhat of a resurgence (hello, tracksuits and platform shoes). Some looks may never come back—frosted tips, we’ll see you... maybe never—but others have stood the test of time.

Today's red carpet icons adopted some of the heyday's trendiest fits while others forged their own unique style path. Take a look at what your favorite celebs wore in 1999 versus what they’re wearing now in 2019.

While some stars may avoid bold fashion statements later in their careers, Jeff Goldblum’s wardrobe—once generic and understated—has upped the ante. In 1999, he kept his look simple and sophisticated. Loose suits and muted tones defined a typical ‘90s Goldblum; even his eyewear flew under the radar with barely noticeable frames.

2019 Jeff is an entirely new breed. To those who thought Goldblum’s glory days began and ended with the Jurassic Park and Independence Day films, think again. The pop culture icon remains as relevant as ever with an undying fan base (James Corden created a laudatory “thank u, next” parody in his honor called “thank u, jeff”) and red carpet styles you cannot miss. This 2019 look—bursting with animal prints, bold colors and even fur—showcases Jeff’s reborn style: confident, adventurous and suave. Just like the star himself.

David Beckham’s athleticism made him a household name, but his modern fashion sense has made him a red carpet favorite. What else should we expect from the man who married Posh Spice (in 1999, in fact!)? Off the field, Beckham had not developed a signature style in the late ‘90s, but he certainly kept up with at least one trend: leather. Take this head-to-toe leather ensemble: a perfect example of Beckham’s simultaneously refined and rebellious aura.   

With his sports career behind him, Beckham’s style choices of today largely reflect the nature of his changing duties: attending formal nights out, business events and even a royal wedding here and there. Posh and Becks continue to draw cameras 20 years later, recently donning a number of elegant looks. And Beckham never fails to “wow” crowds with chic, well-tailored formalwear.

Have trouble believing 20 years passed between these two photos? Because… same. Though Will Smith may look like he hasn’t aged a day since he “became the prince of a town called Bel Air,” his style choices certainly have adjusted. Like Beckham, Smith wore leather pieces back in 1999. Though, like this silver jacket shows, he still enlivened his wardrobe with more eccentric pieces.

The press tour for Disney’s Aladdin remake this year gave Smith plentiful red carpet opportunities. Comfortable, semi-casual and sometimes adventurous looks have been Smith’s go-tos. He’s graced recent press appearances in slacks, trench coats, sweaters and printed suits (like the one above). Smith’s style evolution over the past two decades shows a willingness dabble in trends without making a major statement. He’s playing it as cool as ever.

Spike Lee, a renowned Hollywood great, scored his first Academy Award this year with his screenplay adaptation of BlacKkKlansman. But Lee made his way onto the film scene way back in 1986 with She’s Gotta Have It, his directorial debut. In those early days, he established a few key staples: a cap, statement specs and an unceasing love for the New York Knicks (as evident in the pic above).

In 2019, Lee keeps with his go-to sneakers and adventurous eye- and head-wear on red carpets. While he has opted for more traditional suits for award shows and events, more often than not, Lee adds bright colors to the mix. In this outfit, Lee’s newly acquired Academy Award perfectly matches his gold sneaks. A colorful suit, shirt and tie create a look that speaks to his one-of-a-kind creative outlook.

Denim-on-denim may have been a fashion faux pas at one time, but the all-denim ensembles of the ‘90s made mismatched jeans and jackets not just passable but also fashionable. Three years after he released his debut album, Reasonable Doubt, in 1996, the up-and-coming rapper wore a denim jacket matched with baggy pants and chunky black boots.

Today, Jay-Z has ditched ‘90s grunge for more high-fashion wear. While he stills goes for casual sweatshirts and Yankees baseball caps, the rapper can still rock a brighter, trendier fit, like the ensemble above that he wore to Roc Nation’s pre-Grammy brunch. Jay-Z stays true to his core by dressing it down with white sneakers.

A year before he started filming scenes for The Mummy Returns in 2000, Dwayne “The Rock” Johnson attended the 1999 Emmy Awards as a wrestling superstar. His unbuttoned shirt gives the pro a distinctly relaxed air (and that gold chain necklace screams ‘90s). In the next few years, Johnson’s on-screen career took off, and he began to refine his red carpet style.

The Rock still loves bold patterns on shirts and jackets, but with events like the 2019 Time 100 Gala, he needs a high-fashion look fit for the occasion (he was named to the Time 100 list in 2016 and 2019). This camel-colored suit is dapper yet striking, and the turtleneck underneath harkens back to his famed early ‘90s get-up featuring a chain and fanny pack (the one that inspired many memes).

Ah, the spiky hair of the ‘90s. Young Ryan Reynolds fell victim to this passing craze in 1999, pictured above at the Election movie premiere. A light goatee further highlights how much the actor’s grooming and styling have changed. A white tee and short sleeve button-up are so casual. Laid-back ‘90s Ryan clearly did not have his finger on the pulse of high-end fashion in the way that he does today.

Gone is the hair gel of the past, and 2019 Ryan Reynolds is now frequently named among the most fashionable male celebrities. He always seems to find that elusive, ideal middle ground between over- and underdressing for the occasion. This fit is a prime example. The denim vest gives this look a casual flare (and throws it back to that ‘90s denim mania) while still keeping up with maintaining that formal feel with a khaki-colored suit.

Hair slightly unkempt and coffee cup in hand, 1999 Rob Lowe rolled up to a pre-Oscar party in the way only an already well-established star could. While dressing up for more formal occasions, Lowe kept to tan and black leather jackets and casual shirts whenever he could. The West Wing had its first season that year, and he eventually received Emmy and Golden Globe nominations. Lowe’s comeback had just begun.

Twenty years later, the star’s look is distinguishably clean-cut, exuding vacation vibes. Youthful and relaxed, his cultivated style choices have kept the 55-year-old actor looking sharp.   

1999 Matthew McConaughey sported casual, borderline grunge pieces. An adopter of the leather trend, McConaughey wore a tan leather jacket (above) to the premiere of EdTV, a box office flop starring Woody Harrelson and Ellen DeGeneres that The Atlantic described as a film that “brutally reeks, head to toe, of the '90s.” McConaughey would soon find his calling as a rom-com star in the 2000s, but he rode out the end of the decade in style.

Present-day McConaughey keeps his style cool and funky. While he’s certainly worn smart, sophisticated suits, he’ll also frequently put on cargo or leather jackets for laid-back fits. This McConaughey look features a vest-and-pants combination that, sans a more formal jacket, keeps with his easygoing vibe. The tinted classes complete the look.

George Clooney’s 1999 ensemble may make you question whether celebrities in the ‘90s ever wore clothes that fit. Oversized suits became all the rage in the ‘80s and ‘90s as offices became more casual. Big, loose suits have made a definite comeback recently and even extended into womenswear. Clooney’s suit would have been perfectly on-trend, and variations of this look have graced runways in the past few years.

If Clooney’s modern looks are any indication, he’s not one to take a significant fashion leap. His outfits stick to simple shades: black, gray and blue. For the Catch 22 U.K. Premiere, he donned a head-to-toe black fit. Clooney knows what works for him and rarely strays from the classics.

Read More: The Rock in 2001 Is an Endless Summer Mood