People who know how to dress for success!!!

I use to be big on getting dress up anywhere I went. I use to like wearing suits and fancy clothes because it represent me having class and good taste in fashion. I use to like looking all fly for the ladies when I was in high school and college. Some of the male actors impressed me to look good for the girls because I may end up with one due to what I wore. Even though I do not know anything about women's fashion included some of females on this list so they wouldn't feel left out. Please keep in mind even if a celebrity is known for wearing mismatch clothes, but dress well one time, I will still include him or her on the list. Makes sense. Let's get this party started!
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1.
Sean Combs
Soundtrack, Training Day
Sean Diddy Combs, AKA Puff Daddy, is the definition of a mogul. Starting his career as the director of A&R at Uptown Records, he was integral in launching the careers of Mary J. Blige and Jodeci, and later started his own label, Bad Boy Records, which has fostered talent that includes Mariah Carey, Method Man...
“ I like when P Diddy rock his famous tuxedos during big award shows, such as The Oscars or The Grammies. ” - horne_jeffrey
 
2.
Dwayne Johnson
Actor, WWE Raw
Dwayne Douglas Johnson, also known as The Rock, was born on May 2, 1972 in Hayward, California, to Ata Johnson (born Feagaimaleata Fitisemanu Maivia) and Canadian-born professional wrestler Rocky Johnson (born Wayde Douglas Bowles). His father is black (of Black Nova Scotian descent), and his mother is of Samoan background (her own father was Peter Fanene Maivia...
“ The Rock used to know how to rock those expensive button down shirts with the leather pants in the early 2000s. ” - horne_jeffrey
 
3.
Bill Cosby
Music Department, Bill Cosby: Himself
Bill Cosby is one of the world's most well-known entertainers and comedians. William Henry Cosby, Jr. was born on July 12, 1937, in Philadelphia, Pennsylvania, to Anna Pearl (Hite), a maid, and William Henry Cosby, Sr., a U.S. Navy sailor. After tenth grade, Cosby joined the Navy and completed high school through a correspondence course...
“ I use to like some of Bill Cobsy sweaters in the 80s and 90s. ” - horne_jeffrey
 
4.
Ludacris
Soundtrack, The Hangover
Ludacris was born Christopher Brian Bridges in Champaign, Illinois, where he was raised, the son of Roberta Shields and Wayne Brian Bridges. He is African-American, and has said that he also has Native American ancestry. At nine years old, he started rapping. He attended Emerson Middle School and, eventually...
“ Luda knows how to mix his clothes up by wearing suit and sweats when the ocassion calls for it. I like how he wore clothes that people had it seen before in the 2000s. ” - horne_jeffrey
 
5.
Jay Z
Shawn Corey Carter was born 4 December 1969 in Brooklyn, New York, USA. Raised in Brooklyn, Carter was a school friend of The Notorious B.I.G.. He first started releasing records in the late 1980s. In 1990, he appeared on records by his close friend, Jaz ("The Originators") and Original Flavor ("Can I Get Open")...
 
6.
50 Cent
Actor, Spy
Born in the South Jamaica section of Queens, Curtis "50 Cent" Jackson has lived in New York City all his life. He was raised by his grandparents after his father ran out and his mother was shot when he was only eight. Growing up, the Queens rapper originally wanted to be a heavyweight boxer, but eventually fell back on rapping...
 
7.
Halle Berry
Halle Berry was born in Cleveland, Ohio. Her father, Jerome Jesse Berry, was African-American, and worked as a hospital attendant. Her mother, Judith Ann (Hawkins), who is Caucasian, has English and German ancestry, and is a retired psychiatric nurse. Halle has an older sister named Heidi Berry...
“ So far the only female on this list because I heard great things about Halle Berry being great dresser. Also, I am bias because she is still hot in her 40s. I am sorry ladies I have no sense of fashion when it comes to choosing what looks good on your bodies. So when we are at a clothing store please do not ask me if this looks good on you because I will say anything to leave the store. Do you by taking you time to shop while I sitdown in the store staying out of your way. Ok? Thank you. ” - horne_jeffrey
 
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9.
Michael Jackson
Thanks, This Is It
Michael Joseph Jackson was born in Gary, Indiana on August 29, 1958, and entertained audiences nearly his entire life. His father, Joe Jackson, had been a guitarist, but was forced to give up his musical ambitions following his marriage to Katherine Jackson (née Katherine Esther Scruse). Together...
 
10.
Damon Dash
Damon Dash sent himself to boarding school because he wanted a better education than he was receiving at the time. As a result, his "street credibility" was initially questioned at the onset of his career. Dash received his official start in the music industry when he produced 90's rap group, Original Flavor's first album...
 
11.
Cam'ron
Soundtrack, End of Watch
Rapper Cam'ron was born and raised in Harlem, attending Manhattan Center High School, where one of his basketball teammates was Mason "Mase" Betha, who also became a successful rapper. Though his playing earned him scholarship offers from top colleges, Cam'ron was unable to take advantage of them because of his poor academic record...
 
12.
Jennifer Lopez
Actress, Out of Sight
Jennifer Lynn Lopez was born in the Castle Hill section of the South Bronx on July 24, 1969. She is the middle of three musically-inclined sisters, Leslie Lopez, a homemaker, and Lynda Lopez (aka Lynda Lopez), a DJ on New York's WKTU, a VH1 VJ, and a morning news show correspondent on New York's Channel 11...
“ She has wore some clothes that has grabbed people's attention over the years. ” - horne_jeffrey
 
14.
Woody Harrelson
Academy Award-nominated and Emmy Award winner Woody Harrelson was born on July 23, 1961 in Midland, Texas, to Diane Lou (Oswald) and Charles Harrelson. He grew up in Lebanon, Ohio, and, after receiving degrees in theater arts and English from Hanover College, had a brief stint in New York theater. He was soon cast as Woody on TV series Cheers...
“ He is on the list because I remember when he wore that fly white tuxedo during early 1997, which was way ahead of its time. ” - horne_jeffrey
 
16.
Gabrielle Union
Actress, Bad Boys II
Gabrielle Union was born on October 29, 1972, in Omaha, Nebraska, to Theresa (Glass), who managed a phone company, and Sylvester E. Union, a military sergeant and business executive. At the age of 8, her family moved to Pleasanton, California, where she grew up and attended high school. In high school...
 
17.
Tupac Shakur
Soundtrack, Django Unchained
Born in New York City, Tupac grew up primarily in Harlem. In 1984, his family moved to Baltimore, Maryland where he became good friends with Jada Pinkett Smith. His family moved again in 1988 to Oakland, California. His first breakthrough in music came in 1991 as a member of the group Digital Underground...
“ I use to dig his fashion trend in the 90s. He use to know how to rock the pants, boots, vest, hoodies, and jean jackets, which was ahead of his time. He know how to wear a suit when the ocassion called for it. ” - horne_jeffrey
 
18.
Nicole Kidman
Actress, Moulin Rouge!
Elegant blonde Nicole Kidman, known as one of Hollywood's top Australian imports, was actually born in Honolulu, Hawaii, while her Australian parents were there on educational visas. Kidman is the daughter of Janelle Ann (Glenny), a nursing instructor, and Antony David Kidman, a biochemist and clinical psychologist...
“ Two words! 2007 Oscars! Nuff said. ” - horne_jeffrey
 
19.
“ I hear some people say Joan Rivers know how to dress. I have her on the list because she is funny when she cracks on people's clothes during the Oscars. It sounds like she knows what she is talking about in what goes and does not go on people's bodies. So I give credit when it is due. ” - horne_jeffrey
 
20.
Nelly
Soundtrack, Bad Boys II
Nelly went to Spain with his father, Air Force Man Cornall Haynes Sr., until he was 3 years old, then moved to St. Louis. Nelly's folks struggled financially and split up when he was 7. As the youngest child in the neighborhood he grew up getting into trouble with the big kids. As a result he ended up moving around to live with various family members...
“ Nelly is on the list because I like when he wear his jersey backwards, which was creative and unique in the early 2000s. Also, I included him on this list because he made air force ones more popular back in the day. ” - horne_jeffrey
 
22.
Steve Wilkos
Steve Wilkos is the host of NBCUniversal Domestic Television Distribution's nationally syndicated series The Steve Wilkos Show. A native of Chicago, Wilkos served his country in the U.S. Marine Corps for almost seven years before joining the Chicago Police Department. For almost 12 years, he kept the...
“ I like the button down shirts he always wears during his shows because they are casual yet professional simultaneously. In fact, he sort inspired me to wear more button down shirts for job interviews and hanging out purposes. ” - horne_jeffrey
 
23.
Eddie Murphy
Edward Regan Murphy was born April 3, 1961 in Brooklyn, New York, to Lillian, a telephone operator, and Charles Edward Murphy, a transit police officer who was also an amateur comedian and actor. After his father died, his mother married Vernon Lynch, a foreman at a Breyer's Ice Cream plant. His siblings are Charlie Murphy and Vernon Lynch...
“ I like the clothes he wore in The Nutty Professor and Boomerang. ” - horne_jeffrey
 
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“ One of the best dress guys around. I like how he knew how to dress well while being funny, which can be tricky to do. Sometimes, when people get dress up it seems to change their mood, which means people may act serious when they are in a business suit. Not Cedric. He acts a fool in a tux the same way he would act if he wore sweats. ” - horne_jeffrey
 
26.
Nicki Minaj
Soundtrack, Despicable Me 2
Onika Tanya Maraj, better known as Nicki Minaj was born on December 8, 1982 in Saint James, Trinidad and Tobago and raised in Jamaica, Queens, New York. She grew up in a troubled family with a father that was a drug addict who later changed after he checked into rehab and started going to church. Minaj went to LaGaurdia High School and studied singing and acting...
 
27.
Lady Gaga
Lady Gaga, born Stefani Joanne Angelina Germanotta, is an American songwriter, singer, actress, philanthropist, dancer and fashion designer. Gaga was born on March 28, 1986 in Manhattan, New York City, to Cynthia Louise (Bissett) and Joseph Anthony Germanotta, Jr., an internet entrepreneur. Her father is of Italian descent...