While in high school, he worked first for Thom McAn dyeing women’s shoes and then the Anderson-Little men’s store, where he sold suits. As a college student, he worked part-time at Louis Boston. Abboud became a buyer at Louis Boston at age 23. Over the course of twelve years, he served as buyer, merchandiser, and eventually coordinator of promotion and advertising.

Abboud joined Ralph Lauren in 1981, eventually becoming associate director of menswear design. He launched his own label in spring 1987. In 1988, JA Apparel was created as a joint venture between Abboud and GFT (Gruppo Finanziario Tessile) USA.

In 1991 Abboud worked with fashion director Peter Speliopoulos. Abboud was the first designer to win the CFDA award as Best Menswear Designer two years in a row. Many of Abboud's famous friends are also his customers, including American trumpeter and composer Wynton Marsalis, author and former TV news anchor Tom Brokaw, and former Boston Red Sox shortstop Nomar Garciaparra.

Abboud sold his trademarks and name to JA Apparel for $65 million in 2000. The company was acquired by private-equity firm J.W. Childs Associates for $73 million in 2004, and Abboud left JA Apparel in 2005.

Abboud launched a new line called Jaz in 2007. He also created the Black Brown 1826 line for the Lord & Taylor department store in 2008. The year 2008 also marked the opening of Abboud's first stores in China.

In 2010, Abboud became the chief creative officer of HMX, owner of the Hart Schaffner Marx and Hickey Freeman brands. HMX made an offer to buy JA Apparel for $90 million in 2011. In December 2012, he became Chief Creative Director of Men's Wearhouse. While employing Abboud as its creative director, Men’s Wearhouse Inc. (now Tailored Brands Inc.) reacquired the Abboud trademark in 2013.

After getting back the legal right to his brand in 2013, Abboud set up e-commerce, opened a Madison Avenue flagship store and produced full-scale fashion shows.

Abboud wrote Threads: My Life Behind the Seams in the High-Stakes World of Fashion in which he thoroughly describes the fashion industry from designing and selling clothes to naming colors. He also writes about some of the negative experiences that he has endured such as racial profiling after the September 11 attacks, a court battle over legal rights to his name, and a failed flagship store that is now occupied by Donna Karan.

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