Star Style Evolution: Leonardo DiCaprio
![//wenn](https://media.radaronline.com/brand-img/pCccce2SS/480x251/2010/07/wenn123492.jpg?position=top 480w, https://media.radaronline.com/brand-img/pCccce2SS/640x335/2010/07/wenn123492.jpg?position=top 640w, https://media.radaronline.com/brand-img/pCccce2SS/768x402/2010/07/wenn123492.jpg?position=top 768w, https://media.radaronline.com/brand-img/pCccce2SS/1024x536/2010/07/wenn123492.jpg?position=top 1024w, https://media.radaronline.com/brand-img/pCccce2SS/1280x670/2010/07/wenn123492.jpg?position=top 1280w, https://media.radaronline.com/brand-img/pCccce2SS/1440x753/2010/07/wenn123492.jpg?position=top 1440w, https://media.radaronline.com/brand-img/pCccce2SS/1600x837/2010/07/wenn123492.jpg?position=top 1600w, https://media.radaronline.com/brand-img/pCccce2SS/2160x1130/2010/07/wenn123492.jpg?position=top 2160w)
July 14 2010, Published 1:43 p.m. ET
Star Style Evolution: Leonardo DiCaprio
1. 1996: Leonardo achieved heartthrob and leading man status with the release of, Romeo + Juliet, which pulled in $147 million at the box office. Unfortunately, he had a little crutch that year. We can’t say we were crazy about his shiny green shirt, but hey, it was the nineties!
![//leonardodicaprio](https://media.radaronline.com/brand-img/jO2NuVQEp/0x0/2010/07/leonardodicaprio1996001.jpg)
1996: Leonardo achieved heartthrob and leading man status with the release
of, Romeo + Juliet, which pulled in $147 million at the box office.
Unfortunately, he had a little crutch that year. We can’t say we were crazy
about his shiny green shirt, but hey, it was the nineties!
2. 1997: Leonardo was dressed to impress at the Los Angeles premiere of Titanic, well suited for the boat-based masterpiece in navy blue. The star had no idea the award-winning film would go onto be the highest-grossing film of its time, taking in over $1.8 billion.
![//wenn](https://media.radaronline.com/brand-img/vPw1qRWZy/0x0/2010/07/wenn866295.jpg)
1997: Leonardo was dressed to impress at the Los Angeles premiere of
Titanic, well suited for the boat-based masterpiece in navy blue. The star
had no idea the award-winning film would go onto be the highest-grossing
film of its time, taking in over $1.8 billion.
3. 1998: At the Golden Globe Awards with his costar Kate Winslett, Leo still looked like a little boy in a black tuxedo.
![//dicapriowinslett](https://media.radaronline.com/brand-img/-I1yJAPIE/0x0/2010/07/dicapriowinslett11898.jpg)
1998: At the Golden Globe Awards with his costar Kate Winslett, Leo still
looked like a little boy in a black tuxedo.
4. 1998: Leo with French actor Gerard Depardieu at the Parisian premiere of The Man in the Iron Mask, looked sophisticated in a black suit.
![//wenn](https://media.radaronline.com/brand-img/tkJich4ZS/0x0/2010/07/wenn3813.jpg)
1998: Leo with French actor Gerard Depardieu at the Parisian premiere of The
Man in the Iron Mask, looked sophisticated in a black suit.
5. 1999: Leo dated model Kristen Zang on-and-off through the 1990’s, who joined him at Magic Mountain for a celebrity charity event. The two were clad in dressed down duds.
![//leodicaprio](https://media.radaronline.com/brand-img/Re7hOW-v2/0x0/2010/07/leodicaprio052799001.jpg)
1999: Leo dated model Kristen Zang on-and-off through the 1990’s, who joined
him at Magic Mountain for a celebrity charity event. The two were clad in
dressed down duds.
6. 2000: Once again starring in a film based around the ocean, Leo rocked an all navy blue ensemble to the Los Angeles premiere of The Beach.
![//wenn](https://media.radaronline.com/brand-img/txfy5-vqJ/0x0/2010/07/wenn9800.jpg)
2000: Once again starring in a film based around the ocean, Leo rocked an
all navy blue ensemble to the Los Angeles premiere of The Beach.
7. 2003: Leo bulked up and sported some facial fuzz to the UK premiere of Gangs of New York.
![//wenn](https://media.radaronline.com/brand-img/7yYmQCyuR/0x0/2010/07/wenn1237798.jpg)
2003: Leo bulked up and sported some facial fuzz to the UK premiere of Gangs
of New York.
8. 2004: Leo was very involved in John Kerry’s presidential campaign. Not only did he contribute financially and campaign for the politician, but he also rocked his shirt to a premiere in NYC.
![//wenn_ _](https://media.radaronline.com/brand-img/4v9n2UfMQ/0x0/2010/07/wenn123492_-_1.jpg)
2004: Leo was very involved in John Kerry’s presidential campaign. Not only
did he contribute financially and campaign for the politician, but he also
rocked his shirt to a premiere in NYC.
9. 2004: Leo, accompanied by costar Cate Blanchett and one of his biggest fans (and employers!) Martin Scorsese, looked devastatingly dapper in a black suit at the NYC premiere of The Aviator.
![//wenn](https://media.radaronline.com/brand-img/tdDglaZ5F/0x0/2010/07/wenn153459.jpg)
2004: Leo, accompanied by costar Cate Blanchett and one of his biggest fans
(and employers!) Martin Scorsese, looked devastatingly dapper in a black
suit at the NYC premiere of The Aviator.
10. 2004: Leo had a grey day at the London premiere of The Aviator, looking super GQ in his perfectly tailored suit.
![//wenn](https://media.radaronline.com/brand-img/JEoNDZHjm/0x0/2010/07/wenn155180.jpg)
2004: Leo had a grey day at the London premiere of The Aviator, looking
super GQ in his perfectly tailored suit.
11. 2005: Leo’s Brazilian supermodel girlfriend Gisele Bundchen escorted the actor to the Academy Award, where his was nominated for his portrayal of Howard Hughes in The Aviator.
![//wenn](https://media.radaronline.com/brand-img/7qOsy5e42/0x0/2010/07/wenn187754.jpg)
2005: Leo’s Brazilian supermodel girlfriend Gisele Bundchen escorted the
actor to the Academy Award, where his was nominated for his portrayal of
Howard Hughes in The Aviator.
12. 2006: Leo rocked a sassy striped tie to the Rome Film Festival premiere of The Departed, where he was flocked by Martin Scorsese and Vera Farmiga.
![//wenn](https://media.radaronline.com/brand-img/Eiw7uzRWE/0x0/2010/07/wenn896585.jpg)
2006: Leo rocked a sassy striped tie to the Rome Film Festival premiere of
The Departed, where he was flocked by Martin Scorsese and Vera Farmiga.
13. 2007: At the Critics Choice Awards, Leonardo looked dapper in black.
![//wenn](https://media.radaronline.com/brand-img/igFNgwEDr/0x0/2010/07/wenn1052748.jpg)
2007: At the Critics Choice Awards, Leonardo looked dapper in black.
14. 2007: At the Cannes Film Festival screening of the 11th Hour, the environmentally aware actor looked super hunky in black.
![//wenn](https://media.radaronline.com/brand-img/sa2aZbuSg/0x0/2010/07/wenn1344607.jpg)
2007: At the Cannes Film Festival screening of the 11th Hour, the
environmentally aware actor looked super hunky in black.
15. 2008: Leo reunited with Kate Winslet for Revolutionary Road, looking all grown up eleven years after he walked the carpet with her for Titanic.
![//wenn](https://media.radaronline.com/brand-img/JnVRPU-eA/0x0/2010/07/wenn2219251.jpg)
2008: Leo reunited with Kate Winslet for Revolutionary Road, looking all
grown up eleven years after he walked the carpet with her for Titanic.
16. 2009: The dynamic onscreen duo got all dressed up for The Golden Globes, where Leo was nominated for Best Actor.
![//wenn](https://media.radaronline.com/brand-img/XlGyaK5Na/0x0/2010/07/wenn2245007.jpg)
2009: The dynamic onscreen duo got all dressed up for The Golden Globes,
where Leo was nominated for Best Actor.
17. 2010: Not a young boy anymore, Leo walked the red carpet of the London premiere of Inception, wearing a gorgeously grey suit.
![Radar Logo](/radar_logo.png)
![//infphoto_](https://media.radaronline.com/brand-img/gZV_qhzMg/0x0/2010/07/infphoto_1340056.jpg)
2010: Not a young boy anymore, Leo walked the red carpet of the London
premiere of Inception, wearing a gorgeously grey suit.
18. 1990: Leo scored his first role on the television show Parenthood. The blonde child actor was ready for super stardom from the start.
![//dicaprio_jm](https://media.radaronline.com/brand-img/yCI7s0TF0/0x0/2010/07/dicaprio_jm99999.jpg)
1990: Leo scored his first role on the television show Parenthood. The blonde child actor was ready for super stardom from the start.
19. 1990's: The sporty child actor loved having his picture taken.
![//_reih](https://media.radaronline.com/brand-img/rFf73Ygti/0x0/2010/07/19980602_reih.jpg)
1990's: The sporty child actor loved having his picture taken.
20. 1992: At MTV's Rock n' Jock Basketball Tournament, Leo sported a jersey.
![//_](https://media.radaronline.com/brand-img/YSae-sZiw/0x0/2010/07/74711505_10.jpg)
1992: At MTV's Rock n' Jock Basketball Tournament, Leo sported a jersey.
21. 1995: With Mark Wahlberg, the Basketball Diaries star dressed up for the red carpet.
![//_](https://media.radaronline.com/brand-img/JOtMmh-MM/0x0/2010/07/77935556_10.jpg)
1995: With Mark Wahlberg, the Basketball Diaries star dressed up for the red carpet.