Angelina Jolie has had a bit of a weird past. There were rumors about her love affair with her brother and the odd relationship with Billy-Bob Thornton. Her fashion sense reflected that time in her life. She almost always dressed in grunge, but all that changed when she got older.
Today, her wardrobe is a masterclass in quiet luxury and timeless minimalism. She has swapped out the dramatic leather and monochromatic black of her youth for a sophisticated palette of soft neutrals, including creams, tands, and crisp whites. Her modern signature look relies on elegant, structured silhouettes—think tailored trench coats, flowing silk midi dresses, and perfectly draped capes.
Drew Barrymore had a rough childhood. She was an alcoholic at 11 and a drug addict by 12. Over the years, she cleaned up her act and became one of the best actresses of her age. When she was younger, she wore what any teenager would wear – jeans and a t-shirt.
As she grew, she went grungy, but it didn't last long. She eventually got into fashion and made her own makeup line called FLOWER Beauty. To match that, her style has improved.
Whether it was for attention or just a statement, Ozzy’s daughter, Kelly Osbourne, had a unique fashion sense when she was younger. Kelly Osbourne's wardrobe was the ultimate embodiment of angsty, mall-goth rebellion and pop-punk chaos. She routinely rejected the polished, sun-kissed Hollywood aesthetic of the era in favor of a chaotic, DIY look defined by heavy black eyeliner, safety-pin accessories, fishnets, and graphic band tees.
While she still has a flair for the odd (like purple hair), she completely changed the way she looked. She lost weight and started to wear outfits that were quite fashionable. She still loves darker colors, but there's no more grunge.
During his early years in One Direction, Harry Styles's wardrobe was the definition of wholesome, quintessential boy-band chic with a distinctly British, collegiate twist. The look relied heavily on preppy, youthful staples: tailored blazers layered over casual graphic tees, crisp white button-downs, skinny colored chinos, and his signature Jack Wills hoodies.
Following his departure from the boy band, his wardrobe underwent a radical, high-fashion transformation into something entirely his own. He became a fearless champion of gender-fluid, maximalist style, frequently sporting bold, 1970s-inspired custom Gucci suits, sheer blouses, pearl necklaces, and dramatic feather boas on the red carpet. Moving into his newer musical eras, his look has shifted yet again toward a more refined, retro-disco aesthetic that seamlessly blends sleeker, office-inspired tailoring with playful, tongue-in-cheek casualwear.
Beyonce was a member of Destiny's Child, and her style often reflected what the other members wore – they had to match! Because she grew in popularity during the '90s, she wore what was popular. That was usually jeans with designs and bandana or halter tops.
Decades later, Beyoncé’s modern aesthetic has evolved into a commanding, high-fashion spectacle where she dictates the global style conversation rather than following it. While her everyday wardrobe leans into sleek, ultra-curated "quiet luxury," her visual album eras and stadium tours have turned her into a conceptual fashion chameleon. She has swapped out her mother's home-sewn matching sets for custom, avant-garde masterpieces from the world's elite fashion houses.
In the early days of her career, Lady Gaga’s wardrobe was an explosive, boundary-pushing exercise in pop-culture performance art that treated the public eye as a 24/7 theater. She burst onto the scene in the late 2000s and early 2010s, rejecting standard pop-star glamour in favor of avant-garde shock value, famously donning structural origami dresses, towering Alexander McQueen "Armadillo" heels, an egg-like vessel she was carried in, and, most notoriously, a dress entirely constructed from raw meat.
Anyone that grew up in the ‘80s can tell you that you had to have a power suit with shoulder pads to be considered an adult. This was Julia Robert’s style in the ‘90s. In fact, she wore a power suit to the golden globes in 1990.
We’re happy to say that she dresses much differently nowadays. She can be classy, like when she’s at an award show, or casual when she’s just sitting at the beach.
Gone are the Fight Club days – well, sort of. While Brad Pitt doesn’t look as young anymore, he still looks pretty dang good. In the ’90s, he looked more like a surfer boy or a bad boy, but with time comes change.
Brad is now a father and dresses like one when he’s out and about. Sometimes he does have long hair, but we’re happy to see that he styles it. More often than not, as of late, he's been shaving his head.
True to her name, Pink's early aesthetic was anchored by a rotating canvas of electric, fluorescent pink hair—often styled into spiky, gravity-defying locks or a raw fauxhawk. Her wardrobe was a loud, chaotic explosion of anti-establishment Y2K punk-rock rebellion, loaded with low-rise cargo pants.
Off the stage and on the red carpet, she has traded the chaotic patterns of her youth for a sleek, monochromatic approach to fashion—frequently stepping out in stark black maxis, sharp blazers, and tough-luxe studded leather jackets. Her hair has similarly matured from neon dyes into a signature, ice-platinum pixie cut.
Nicki Minaj came into the game singing pop, but she was always active in the rap scene. As she became more popular, she was able to do what she wanted, and she went from Starships to Chun-Li. Her style also changed.
Less purple, less color, and more natural. Nicki now rocks her natural hair color and wears clothing that’s much more flattering.
Victoria may have been Posh Spice in the ‘90s, but now she’s a businesswoman, fashion designer, and model. Back then, wearing platform shoes and revealing clothing was just the way things were.
Now that she’s married and a designer, she has changed her looks. Now, she’s always classy, and she’s regained the name “Posh.” If you use anyone as a style icon, it should be Victoria Beckham.
When Taylor Swift first burst onto the music scene in the mid-2000s, her wardrobe was a quintessential celebration of teenage country-boho charm. Her signature look was instantly recognizable: a cascade of long, natural blonde ringlets, simple cotton sundresses, and heavily worn cowboy boots.
Today, she has masterfully refined her millennial roots into a mature, elevated take on preppy chic—routinely stepping out in New York City wearing structured outerwear from The Row, high-end Thom Browne tailoring, and romantic, airy pieces from labels like Dôen and Reformation.
During her Disney Channel days as Hannah Montana, Miley Cyrus’s wardrobe was the absolute blueprint for late-2000s tween pop stardom: cropped denim vests stacked over rhinestone-encrusted tank tops, ruffled mini skirts awkwardly layered over skinny bootcut jeans, and shiny metallic bomber jackets. No outfit was complete without a barrage of non-functional accessories, including skinny sequined scarves, fingerless gloves, and wide, corset-style statement belts.
Today, her aesthetic has evolved into a commanding, hyper-luxurious celebration of 1970s rock-and-roll decadence and archival couture. Often referred to as her "Cher era," Miley has swapped the plastic, neon club-kid gear for sophisticated, high-fashion edge, frequently commanding major red carpets in plunging Tom Ford pantsuits, sculptural Saint Laurent leather gowns, and rare vintage masterpieces from houses like Bob Mackie and Alexander McQueen.
When Anne Hathaway was trying to find her way in Hollywood, she wasn’t really sure how to dress. She often went for colorful pieces with intense designs.
Now that she’s older, she chooses more neutral colored outfits. Hathaway also manages to always look incredibly elegant no matter what she’s doing. We’re not sure how she does it.
Gwen Stefani was the lead singer of No Doubt, a band that rebelled against modern music. Her style was erratic. It was like every day was an outdoor festival for her.
Skip ahead a decade (or more), and Stefani has changed completely. Her outfits are still incredibly stylish, but she doesn’t show off her body as much as she did before.
In the late 1990s and early 2000s, Justin Timberlake was the absolute poster boy for Y2K boy-band excess as the frontman of NSYNC. His style back then was a loud, high-octane mix of pop-star flash and streetwear experimentation, defined by oversized leather jackets, massive tinted sunglasses, baggy tracksuits, and heavily accessorized jewelry. Nothing captured the peak of this era quite like his iconic, gravity-defying "frosted tips" curls, or the infamous, head-to-toe matching denim "Canadian tuxedo" he wore to the 2001 American Music Awards.
Today, his aesthetic has matured into a sleek, high-end interpretation of modern streetwear and tailored sophistication. Long gone are the baggy silhouettes and frosted hair, replaced by a refined look that frequently relies on sharp, custom Tom Ford suits for the red carpet and structured, elevated casualwear for his tours. His contemporary style effortlessly blends luxury fashion with a relaxed, mature edge—frequently pairing crisp designer sneakers with tailored trousers, premium knitwear, and high-quality bomber jackets.
In the mid-to-late 1990s, a young Leonardo DiCaprio was the poster boy for effortless, heartthrob cool, leaning heavily into a relaxed, "skater chic" aesthetic. His signature street style relied on oversized, slouchy silhouettes—think baggy, light-wash jeans, chunky knit sweaters, and vintage leather jackets layered over simple white tees. He accessorized with a rotation of backward baseball caps, beanies, and subtle wallet chains, all anchored by his famously messy, curtained blonde hair.
Today, his modern style has shifted into a highly formulaic, ultra-low-profile approach that values anonymity and classic tailoring over fleeting trends. On the red carpet, DiCaprio is a master of fail-safe elegance, almost exclusively wearing impeccable, custom-fitted tuxedos and sharp suits by legacy houses like Giorgio Armani and Dior—though he occasionally breaks up the monotony of classic black and navy with rich, 1970s-inspired chocolate brown tones. Off-duty, however, his style is defined by a deliberate attempt to blend into the crowd; his modern daily uniform consists of plain grey hoodies, standard-fit jeans, canvas sneakers, and a low-brimmed baseball cap.
Cher has always been a style icon in her own league with very few competitors that could even hold a candle to her iconic looks. Cher has never been one for subtlety, opting instead for bright colors, bold statement pieces, and dramatic accessories (e.g., those headpieces).
Now, Cher has mostly traded in her wild headpieces and outfits for a more toned-down style on the red carpet (though, she does still have the wild getups for her tours).
When Nicole Kidman first arrived in Hollywood in the early 1990s, her look was defined by a soft, unrefined bohemian charm. Her signature feature was a wild halo of natural, fiery red ringlets, which she typically paired with minimal makeup, oversized tailoring, and ethereal, bias-cut slip dresses that accentuated her tall, statuesque frame. However, her relationship with fashion completely shifted at the 1997 Academy Awards when she stepped out in a chartreuse John Galliano for Christian Dior gown.
Today, Kidman’s style has evolved into that of a fearless, chameleonic powerhouse of architectural glamour and avant-garde couture. She has traded the soft ringlets of her youth for sleek, polished blonde styles and approaches the red carpet as a form of high-stakes performance art. She consistently dominates major fashion events by collaborating with cutting-edge houses like Balenciaga, Schiaparelli, and Chanel, confidently pulling off everything from heavily sequined, feathered gowns to structured, sculptural takes.
In his early years back in the late '80s, Downey never feared bold statement pieces and out-of-the-box (putting it mildly) looks. For example, the shorts and suit jacket he wore for the premiere of Chances Are back in 1989.
After battling addiction and landing the role in Iron Man, his style was significantly changed. Downey went from too-big suits to perfectly tailored and flattering tuxes. Though, he still likes to pull off a bold look occasionally.
Probably the most drastic change on this list, Caitlyn Jenner reintroduced herself to the public on the cover of Vanity Fair's June 2015 edition after breaking off her marriage with Kris Jenner.
Jenner has always been a fashion icon after debuting as an Olympic Gold Athlete at the 1976 Summer Olympics in Montreal, with bright jackets and classic suits. Now, Jenner sports gorgeous, flowing gowns for the red carpet and cute, casual skirts for everyday life.
Demi Moore emerged onto the scene in the early '80s, sporting a set of blunt and choppy bangs that quickly turned into a more teased and puffed out style to match her eclectic personality.
Since then, her wardrobe has changed drastically and, after her marriage to Ashton Kutcher, her style seemed to take on a younger, more designer-focused look.
Jennifer Lopez has been known for bold and iconic looks (that Versace gown from the Grammy Awards in 2000 attests to that), and her style has switched several times from sheer to sequins, to hip-hop, and everything in between.
As the years have gone on, Lopez's style has evolved into something refined and classic, while still maintaining that bold and iconic style that has landed her on several best-dressed lists.
In the mid-to-late 1980s, Madonna’s style was a high-octane explosion of thrift-shop punk and provocative street-pop rebellion that completely rewritten the rules of female celebrity fashion. Her "Like a Virgin" era signature look was instantly recognizable: a messy, bleached-blonde mop held back by oversized bows, layers of black rubber bracelets, crucifix necklaces worn as jewelry rather than religious symbols, and lace crop tops paired with low-slung tutus.
Today, her wardrobe has evolved into a dark, majestic high-fashion thesis where she rules as a polished, intentional high priestess of avant-garde couture. While she still pays homage to her boundary-pushing roots by incorporating her signature corsetry and fishnets, her modern aesthetic heavily favors "Suitdonna" tailoring, severe Old Hollywood drama, and surrealist gothic theater.
Starting as a childhood star, Johansson's style quickly morphed from innocent to provocative as she grew in the Hollywood industry. At least until the early 2000s hit, which is when all good fashion went down the drain.
Thankfully, Johansson managed to mostly shield herself from the nightmarish outfits of the early 2000s, and since then, her style has come to reflect a classic and sophisticated style that we can't get enough of.
When Charlize Theron first arrived in Hollywood in the mid-1990s, her style perfectly mirrored the era’s "femme fatale meets minimalist" aesthetic. As a former model, she naturally gravitated toward clean, simple lines that highlighted her statuesque frame, frequently hitting early premieres in ultra-sleek black camisole slip dresses, barely-there strappy sandals, and minimalist square-toe heels.
Today, Theron has evolved into what fashion editors call a "new-age minimalist"—a style powerhouse who balances razor-sharp elegance with a distinctly current, high-fashion edge. As a long-standing muse for elite legacy houses like Dior and Givenchy, she has traded her simple '90s slips for commanding, architectural couture on the red carpet. Off-duty and at high-profile events, she masterfully subverts expectations by embracing oversized Saint Laurent tailoring, voluminous fluid trousers, and structured, knee-baring cargo Bermuda shorts.
The star of the movies Heathers and Beetlejuice, Ryder has tried basically every look in the book, jumping from grunge to girly and everything in between. Her role in the cult classic movies have cemented her as a staple in pop culture.
Decades later, her modern aesthetic has evolved into a masterclass in mature, high-concept gothic glamour—proving she never truly abandoned her grunge roots. Rather than pivoting to safe, predictable Hollywood styling, Winona treats her appearances like a sophisticated extension of her iconic, dark-romantic persona.
Aniston has been a style icon since the early '90s, but her style really hit a high when she joined Friends in 1994 and created the classic "Rachel" haircut that still reigns in popularity today. Classic hairstyle aside, Aniston is known for her bold style choices (like wearing a tube top and maxi-skirt to the 5th Annual Screen Actors Guild Awards in 1999).
Today, her wardrobe is the ultimate blueprint for "california-chic minimalism" and effortless, timeless styling. Decades after popularizing the slip dresses and square-toe heels of the '90s, Aniston has barely changed her core style philosophy—because she perfected it early. On the red carpet, she relies on a fail-safe uniform of impeccably tailored, neutral-toned column gowns and her signature, flawlessly cut little black dresses from houses like Dolce & Gabbana and Celine. Off-duty, she defines the "anti-trend" capsule wardrobe, masterfully pairing high-end, relaxed denim—like modern wide-leg or cigarette cuts—with crisp white trainers, simple black turtlenecks, and classic longline coats.
An early 90's grunge style icon, Love was known for her usually-all-black daring, and one-of-a-kind looks paired with dark makeup and styled-messy hair.
After the death of her husband Kurt Cobain, Love left the punk style behind and opted instead for a more classic Hollywood glam look. Though she still likes to throwback to her punk rock roots occasionally.
In the 1990s, Johnny Depp was the undisputed blueprint for effortless, anti-Hollywood heartthrob cool. He completely rejected the clean-cut, muscular leading-man look of the era, opting instead for a gritty, grunge-adjacent "bohemian nomad" aesthetic. His style relied heavily on worn-in, oversized pieces: distressed leather jackets, ripped vintage denim, slouchy flannel shirts, and beat-up combat boots.
Today, his look has evolved into a hyper-accessorized, maximalist style often described as "distressed luxury" or "pirate-rocker chic." While he still favors a rugged edge, he now leans into intentional layering and an obsession with texture—frequently combining relaxed three-piece pinstripe suits with asymmetric, distressed tailoring. He is rarely seen without his signature army of accessories: wide-brimmed fedoras, tinted blue or purple aviator glasses, layered linen scarves, and hands covered in massive silver skull rings and leather bracelets.
