Pennington spent most of his youth in Atlanta. Following high school, he attended Kennesaw College, focusing on art and history. After one year his art professor suggested a career in graphic design, so Pennington started working as a carpenter by day and attending classes at the Atlanta Art Institute by night. After graduation he continued his education at the Atlanta College of Art, studying painting and sculpture while honing his carpentry skills to pay for his education. During his final semester, the handyman was approached by a modeling scout and soon began a lucrative career modeling for various clothing companies and appeared in television commercials.
His breakout moment came in 2000 when he was cast as the enthusisatic carpenter on "Trading Spaces," the decorating series in which two sets of neighbors swap keys to transform a room in each other's home, given two days, $1000, a professional designer and carpenter, and they're not allowed back into their own homes until the moment of truth. During his four-year stint on the TLC series Pennington built an admiring audience (largely female) as the cute, wisecracking and playful carpenter.
He moved over to network television in 2003 as the host of the ABC special "Extreme Makeover: Home Edition." Intended as a one-shot spin-off of the reality series "Extreme Makeover" in which every day people received extensive plastic surgery reworking, the show tweaked the concept by unleashing Pennington and a team of designers and workers to completely renovate an entire house, including landscaping and major interior construction, in an extremely fast seven-day time frame while the unsuspecting family living in the house (nominated by someone in their lives) are whisked away on a vaction until the finale, when the house is unveiled to them. The spin-off proved even more popular in the ratings than the source series and was upgraded to regular weekly airings, and Pennington emerged as one of the the most well-liked reality show hosts on televison.
Pennington's first book, Ty's Tricks was published by Hyperion in 2003 and became a New York Times bestseller. He also signed an exclusive multi-year agreement with Sears, partnering in a broad range of activities, including product design and development, merchandising and advertising, and is the ambassador for the Sears American Dream Campaign. He also tried his hand at acting, appearing in the independent film "The Adventures of Ociee Nash" (2003), playing aviation pioneer Wilbur Wright.