Who can deny the appeal and statement of a well dressed man in a perfectly tailored suit? When made and fit properly by Master Tailors, the custom suit or jacket is every man’s best garment and delivering that garment is the essence of Richard Bennett Custom Tailors.
Our Authentic Bespoke clothing is made by hand right here in our own Chicago shop – we are the last working shop if our kind and scope in the area. Our staff of European Master Tailors has more than 200 years combined experience in the art of Sartorial excellence. In an age of mass replication and off-shore production, we rely on time-tested, “old-fashioned” methods – an approach that has served our clients well for more than 90 years!
A hand crafted garment conforms to your shape over time and is designed to smartly hug the body in the right places and gently release in others. In short, the best looking, most comfortable garment you will ever wear. Every garment is designed, cut and sewn to your precise measurements – to fit right, look great and wear well.
Since 1929, we have been Chicago’s leading custom tailor – hand-crafting the finest suits, jackets, formal wear, trousers, vests and overcoats for the most discriminating clientele. We look forward to being of service!


  • “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.