Robert Downey, Jr.

Downey didn’t fear bold statements pieces or out-of the-box looks in his early years, back in the late 1980s. He wore the suit jacket and shorts that he wore in 1989 for Chances Are’s premiere. His style changed dramatically after overcoming addiction and landing the role as Iron Man. Downey changed from too-big suits and wore perfectly tailored and flattering Tuxes. He does still enjoy a bold look every now and again.

Leonardo DiCaprio

DiCaprio was well-known for wearing baggy bowling shirts and shallow-knit skull caps in the late ’80s to early ’90s. But, his style changed as he got older. DiCaprio started to wear tailored suits in monochromatic, classic colors on the red carpet. He also wore casual cargo shorts for days off. DiCaprio can impress, regardless of the occasion.

Angelina Jolie

Angelina Jolie has a somewhat unusual past. There was talk of her affair with her brother, and her strange relationship with Billy Bob Thornton. This was reflected in her fashion taste. She wore grunge almost all her life. But, that all changed as she grew up. She’s now the epitome o class.

Lady Gaga

Lady Gaga arrived on the scene looking as if she could rival Britney. Gaga was supposed to be the new pop princess, but that didn’t work out. Gaga was a weirdo to begin with, but she wanted to use the brand as a way for her to raise awareness about issues that mattered to them. She wore a meat-colored dress and was able to support social causes with her “Born This Way”. Her outfits have changed quite a bit but it’s unlikely that you will see her wearing a Brittney-esque style again.

Nicki Minaj

Nicki Minaj started out singing pop music, but she was always involved in the rap scene. As she became more well-known, she was able go from Starships to Chun Li. Her style changed too. She is now less purple, more natural, and less colored. Nicki has a natural hair color now and wears flattering clothes.

Jennifer Aniston

Aniston has been a style icon ever since the early ’90s. However, her style was at its peak when she joined Friends and gave birth to the “Rachel” hairstyle that is still very popular today. Aniston is not only known for her classic hairstyle, but she is also well-known for her bold style choices. In 1999, Aniston wore a maxi skirt and tube top to the 5th Annual Screen Actors Guild Awards. The beautiful Little Black Dresses and pantsuits that grace her wardrobe are a constant in her ever-evolving style.

Courtney Love

Love was a grunge style icon in the early 90’s. She is known for her bold, all-black looks and unique, messy-haired hairstyles. Love, who lost her husband Kurt Cobain in 1995, opted for a classic Hollywood look. Although she loves to occasionally harken back at her punk rock roots,

Winona Ryder

Ryder was the star of the movies Heathand Beetlejuice. She has worn almost every look possible, from grunge and girly to everything in between. While her roles in the cult classic movies have made Ryder a household name, her style is still a timeless icon. She has transformed from her 90s grunge with mom jeans and black leather jackets to a more sophisticated, red-carpet-esque style.

Nicole Kidman

Kidman experimented in the late ’90s with bold, bright colors as well as shimmering colors. Kidman gravitates towards neutral designs with just a little sparkle to add glam, rather than overwhelm in recent years. Kidman amazes everyone even after all these decades!

Cher

Cher has been an icon of style in her own right, with few others who could match her iconic looks. Cher was not one to be subtle. She prefers bright colors and bold statement pieces as well as dramatic accessories, such as those headpieces. Cher has mostly given up her wild headpieces, outfits, and bold accessories for a more relaxed style on the red-carpet (though she still does have wild look for her tours).

Justin Timberlake

Justin Timberlake made a name for itself in the mid-90s as a star and he has been a successful solo artist ever since. As he began to build a reputation, he changed his early 2000s fashion choices (like the all-denim outfit he wore with Britney in 2001) and adopted a more mature and sophisticated look.

Anne Hathaway

Anne Hathaway didn’t know how to dress when she was trying find her way to Hollywood. She favored bright, bold pieces with intricate designs. As she ages, she prefers more neutral colors. Hathaway looks elegant, no matter what her outfit is. We aren’t sure how she does this.

Drew Barrymore

Drew Barrymore had a difficult childhood. Drew Barrymore was an alcoholic when she was 11 years old and a drug addict at 12. She improved her acting skills over the years and was one of the most popular actresses her age. As a teenager, she wore jeans and an t-shirt. As she grew older, she became grungy but it didn’t last. She got into fashion, and she started her own line of makeup called FLOWER Beauty. Her style has evolved to match this.

Harry Styles

Harry Styles joined One Direction in the UK. It was a huge success in England and the United States, but Harry Styles couldn’t wait for his chance to break out of his shell. After he had succeeded, he changed from the dull colors to something more. He is seen today wearing flashy jackets or suits with intricate designs. It’s anything other than dull and drab.

Julia Roberts

Everyone who grew-up in the 1980s will recall that you needed to wear a powersuit with shoulder pads to be considered an adults. Julia Robert was known for wearing this type of suit in the ’90s. In fact, she wore a powersuit to the golden globes in 90. We’re glad to say that she now dresses differently. She can be elegant, as she attends an award show, or casual, when she is just relaxing on the beach.

Pink

Pink is her name, but her hair isn’t pink anymore. Although she has blonde hair now, you may see her with very pastel pink hair. She was a star at that time. Some of her looks were very unusual, such as the blue and green jacket she wore to work. Pink’s style is still grungy, but she can now match.

Victoria Beckham

Victoria was Posh Spice in the 90s. But now, she’s a model, fashion designer and businesswoman. It was normal to wear platform shoes and show-off your skin back then. She’s now married and a designer. She is classy now, and she has regained her name of “Posh.” Victoria Beckham should be considered a style icon.

Madonna

Madonna has had a long career, which spans more than four decades. This is why it is expected that her influence would be significant on the fashion industry. Madonna’s style has been reinterpreted many times, including her 1984 ‘Like a Virgin,’ wedding dress and her 1990 Blonde Ambition Tour cone bra. But it still remains trendy and fashionable. FYI, we love this.

Charlize Thron

Charlize theron was known for wearing pantsuits and striped pants in her early days. However, over the years, her style evolved into something more sophisticated and dark with long, fitted dresses and dark pantsuits. Theron’s signature style has always been monochromatic colors such as black, white and grey, with occasional pops in color. However, she is now making more bold fashion choices. She wears lace tights underneath dresses and has lots of fringe.

Jennifer Lopez

Jennifer Lopez is known for bold and iconic looks. The Versace gown at the 2000 Grammy Awards is a perfect example. Her style has also changed several times from sheer to sequins to hip hop and everything in-between. Lopez’s style has changed over the years to be more classic and refined, but still retains that bold and iconic look that made her so popular.

Scarlett Johansson

Johansson started out as a child star. As she grew up in Hollywood, her style changed quickly from innocent and provocative. The good times didn’t end until the 2000s. Johansson was able, thankfully, to keep her head above the paralyzing outfits of the 2000s. Her style has since evolved into a classic, sophisticated style we just can’t stop admiring.

Demi Moore

Demi Moore first appeared on the fashion scene in the early 1980s. Her blunt, choppy bangs quickly transformed into a style that was more teased and puffy to match her eccentric personality. Her style has evolved tremendously since then. After her marriage to Ashton Kutcher her wardrobe changed dramatically.

Johnny Depp

Johnny Depp is known for his quirky and unique looks. Depp made his first appearance in 1980s with t-shirts and leather jackets and fun hats. He quickly expanded his repertoire to include trendy suits in wild colors and vests as well as his classic leather jacket. Depp’s accessories are his greatest asset when it comes to his unique outfits (hats and scarves in particular). We are always impressed by Depp’s daring looks.

Taylor Swift

Taylor Swift was once destined to be a country singer. It was a twist of fate that led to her swapping her boots for heels and boots. As she moved into pop fashion, she became a fashionista quickly. It is hard to see her not wearing something stylish.

Brad Pitt

Gone are the Fight Club days, but not quite. Brad Pitt looks older, but he still looks good. He was more of a surfer boy than a bad boy back in the 1990s. However, time has brought about some changes. Brad is now a father. He dresses up as one when he’s on the streets. Although he kept his long hair, we are glad to see how he styles it.

Beyonce

Beyonce was a member Destiny Child. Her style often mirrored the styles of the other members. Beyonce wore what was in fashion during her rise to fame in the 1990s. It was often jeans with designs and halter tops, or bandanas. But she decided to go solo and everything about her changed. She became more elegant and the Queen of Music was an icon in fashion.

Kelly Osbourne

Kelly Osbourne was Ozzy’s youngest daughter. Kelly was able to make a fashion statement whether she was trying to attract attention or simply be noticed. She has a knack for unusual things, such as purple hair, but she changed her entire look. She began to be more fashionable and lost weight. While she still enjoys darker colors, she isn’t a fan of grunge.

Miley Cyrus

Miley Cyrus may not have been around for very much time, but she’s seen a lot of different styles. She was a Disney star and then a wild child. After she stopped humping foam fingernails, she became more conservative. While she is comfortable in jeans and a T-shirt, she can be seen dressed up from time to time.