Our heritage as Chicago’s leading custom tailor goes back eighty years and three generations. That proud legacy of quality and service endures today and guides our business in every way.

Richard Bennett Custom Tailors History

In the 1920’s, an enterprising salesman named Herb Karoll began selling hats and shirt collars in downtown Chicago. The small shop soon expanded into men’s tailored clothing and sportswear and was renamed Karoll’s Red Hanger Shops – a play on its signature red décor and hangers. The business grew to fourteen stores with its flagship at State and Washington streets in downtown Chicago.

A Chicago institution for over 50 years, Karoll’s ultimately closed in the late 1980’s. Emerging
from the experience was Herb’s grandson, Albert Karoll, who took on the age-old craft of custom tailoring. Calling on customers in their homes and offices, Albert’s formula was simple: the finest, hand-made clothing for business and social occasions plus the convenience of shopping direct.

Richard Bennett Custom Tailors has been the landmark shop for custom-made business clothing in downtown Chicago since the 1950’s. Founded by Mr. Nick Sander, the business was acquired by Albert Karoll in 1998 whom, by then, had expanded his direct-selling business beyond the physical limits of his home-office.
It was a perfect match.Richard Bennett Custom Tailors Grey Suit

In 1929, an Italian immigrant named Dominic DeBartolo began what would become Chicago’s foremost “bespoke” tailoring firm – D. DeBartolo and Company. The flavor was decidedly “old-world”: a small salon where Italian Master Tailors crafted garments the old-fashioned way: entirely by hand from individual patterns developed for each client.

Under Dominic – and later his son Frank’s direction – DeBartolo was widely admired as a leader in style and quality. They attracted clientele from across the country and counted many of Chicago’s business and political elite as customers.

Upon Frank’s death in 2001, DeBartolo stood as one of the last true custom tailors in Chicago. In acquiring the business, Karoll combined their lineage with Richard Bennett’s retail credentials – DeBartolo’s entire staff and pattern archives moved into Richard Bennett’s operation seamlessly. The combined staff quickly jumped into the front of the industry and now stands as Chicago’s authoritative “old-school” tailor shop.

Today, in the heart of Chicago’s business district, we are expanding on that tradition and burnishing our credentials everyday. We continue to hand-tailor in the DeBartolo tradition and deliver top-notch customer service and convenience.

In October 2018, we acquired Riddle McIntyre Shirtmakers – Chicago’s pre-eminent custom shirt maker since 1916. Under the direction of Mr. Frank Kang, we are the last remaining shop of its kind – hand designing and making the finest dress shirts here in our own facility

With genuine Tailors and Shirt Makers working side by side, we are proud to be the only shop of its kind in Chicago and beyond – perpetuating and age-old craft and delivering the finest garments to our clients.

We work hard every day to honor our various business heritages as we pursue every avenue of excellence and customer convenience.

  • “Expert bespoke craftsmanship with a wide array of fabrics done in the old world way. Highly recommended.”

    -Jay G.

  • “It was good to work
    with tailors who are onsite”

    -Cheyenne B.

  • “I just used Richard Bennett Custom Tailors for the first time, and I am impressed. Their staff of experts is professional, personable, and the workmanship is impeccable.”

    -Jeff P.

  • “What a fantastic experience!  They made me a suit EXACTLY to my specifications, and it fits my body perfectly! I am definitely returning to get another custom made suit.”

    -Lauren L.

  • “I have also worked with other top bespoke tailors in London, New York, Montreal, And Toronto.  Richard Bennett is at the top of the game.”

    -Scott P.

  • I can’t stress enough how happy I was with the final product…That final fitting where I got to see my suit in its finished state, I had a HUGE smile on my face.

    -Erica C.