T-shirts to ties: Jon Stewart's fashion and career through the years

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Jon Stewart Through the Years
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T-shirts to ties: Jon Stewart's fashion and career through the years

Long before he became a household name, Jon Stewart broke onto the scene as an MTV host with his own show. In 1993, the funny guy cut his teeth on "The John Stewart Show," a late-night show with a variety of celebrity guests and a fun opening monologue.  His style was very 90s and a little couture immature. In his early days, Stewart regularly hit the town in hoodies and T-shirts and sported dark, curly locks. 
(Photo by Jeff Kravitz/FilmMagic, Inc)

In the 90s, Stewart was also very fond of the leather jacket, T-shirt and jeans look. The dark-haired comedian had a sit down with fellow late-night host Conan O'Brien in 1993 and sans a few gray hairs, the pair look strikingly similar to how they look now.  Photo by: Lesly Weiner/NBCU Photo Bank

Rumors swirled that the young comedian was romancing supermodel Cindy Crawford in the 90s. The pair were spotted all gussied up in 1994 at the MTV Video Music Awards at Radio City Music Hall in New York City. (Photo by Jeff Kravitz/FilmMagic)

In 1995, Stewart met up with singer Jon Bon Jovi. At the time, the New York City native was still sticking to fashion basics like T-shirts. Are you sensing a trend here? (Photo by Ke.Mazur/WireImage)

It's love! Stewart, who wrapped "The Jon Stewart Show" on MTV in 1995, snuggled up to girlfriend Tracy McShane in 1996 at an HBO party. The pair were reportedly set up by a production assistant and clearly couldn't keep their hands off each other during their young romance -- which definitely had staying power. They wed four years after this photo was taken. Perhaps she liked his favorite blue T-shirt as much as  he did. (Photo by Manny Hernandez/Liaison)

Stewart was a rising star in the late 90s -- and as his fame continued to grow, so did his fashion choices. Enter the era of Jon Stewart in more formal attire. (Photo by Ron Galella/WireImage)

In 1999, Stewart attended the  GQ Magazine Of The Year Awards on October 21, 1999, and posed alongside actor Michael J. Fox. During this year, Stewart co-produced several movies like "The Daily View" and "The Daily Show Summer Spectacular." 

(Photo by Ron Galella, Ltd./WireImage)

Look who is getting gussied up now! Stewart looked dapper in a tux at the 1999 Emmy Awards in Los Angeles, despite the fact that it seemed to be a bit big for him. His famous locks were just showing the first signs of a little salt and pepper. (Photo by Frank Micelotta/ImageDirect)

By 1999, Stewart and his now peppered locks, were center stage on Comedy Central's, "The Daily Show." The TV regular replaced Craig Kilborn when he left the show. Naturally, he brought his comedic edge and political prowess to the host seat and a hit was literally born overnight. For his big show, Stewart also stepped up his fashion game and fully traded in his T-shirts for slim-fit suits and well-selected ties.   (Photo by Corey Sipkin/NY Daily News Archive via Getty Images)

Although, he wasn't always suited up. In 2002, the funny guy ditched his clothes in order to host the 44th Annual Grammy Awards.  (Photo by Kevin Winter/Getty Images.

Recognize these two funny faces? Stewart stopped by "Saturday Night Live" in 2002 for a memorable skit with Amy Poehler, where the pair spoofed Mel Gibson. There's no real "fashion moment" here unless you count army greens. 

Photo by Mary Ellen Matthews/NBC/NBCU Photo Bank via Getty Images)

Pretty much everyone fell victim to the political pundit's funny antics -- including Senator Hillary Rodham Clinton, who was all smiles during her 2003 appearance on "The Daily Show." More importantly, Stewart's attire -- dark suit, red tie, crisp white shirt, peppery locks -- became his go-to look for basically the next 10 years. (Photo by Scott Gries/Getty Images for The Daily Show)

All smiles at the Emmys! In 2005, Stewart snagged the Emmy for outstanding individual performance in a variety or music program for his work on "The Daily Show with Jon Stewart." His hair continued to gray, but his boyish smile and love for dark suits don't seem to change. (AP Photo/Kevork Djansezian)

Dark suit, check! Graying locks, check. Another Emmy Award, check. Stewart snagged yet another award for outstanding variety or music series for the "The Daily Show with Jon Stewart" at the 2007 Emmys. (AP Photo/Reed Saxon)

Back to basics! In 2008, a low-key Stewart was spotted goofing around with his son Nathan at a New York Knicks game. Stewart channeled his younger self in a classic T-shirt. His son, also seems to be inheriting his style. (Photo by James Devaney/WireImage)

He's back at it! Stewart grabbed yet another Emmy for his work on "The Daily Show" in 2009. While his looks don't seem to have changed much, one thing is for sure -- he's hired a better tailor at this point in his career. Check out how nicely that penguin suit fits. (AP Photos/Mark J. Terrill)

Recognize this look? Stewart basically added a blazer to his outfit from the Knicks game in order to take the stage next to his pal Stephen Colbert at their Rally to Restore Sanity and/or Fear on the National Mall in Washington D.C. The pair's big rally drew thousands, who were treated to a bevy of laughs with Stewart and Colbert casting themselves as the unlikely pillars of moderation and civility in rough times.  (AP Photo/Carolyn Kaster)

Stewart perfectly complemented President Barack Obama in one of their first interviews. Stewart rocked a red tie while the President wore blue. Talk about a patriotic pairing. (AP Photo/Evan Vucci, File)

Hey there, silver fox!  By 2012, Stewart had given up on his dark locks in favor of his gray tresses, which he began wearing a little longer. The look was mature and sexy all at the same time. Almost as sexy as his Emmy Award for his work on "The Daily Show With Jon Stewart" in 2012.  (Photo by Jordan Strauss/Invision/AP, File)

Stewart clearly understands the power of a red tie during a political interview. For his final sit down with President Barack Obama, Stewart rocked his signature look -- dark suit and a red tie. Some fashion habits really do die hard -- but we aren't complaining. (AP Photo/Evan Vucci, File)

You gotta love that goofy grin. Thanks for all the years, great interviews and for the "Daily Show," Jon. (Photo by Victoria Will/Invision/AP)
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Jon Stewart is hanging up his proverbial hat on Thursday during his final show of "The Daily Show with Jon Stewart," and while it's not goodbye forever for the comedic TV host, it is certainly the end of an era.

Stewart's climb through the television industry has spanned a whopping 30-plus years and throughout his time on the small screen, he's gone from boyish New Yorker with a love of T-shirts to silver fox with serious political prowess. Check out John's fashion and career transformation through the years in the gallery above.
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