Spring 2021
Look Book


Some things never go out of style… the perfect suit – a distinctive necktie – elegant formal wear – personal service… these are the hallmarks of Richard Bennett Custom Tailors.

Since 1929, we have been focused on just one thing – a well-tailored garment that is every bit as serious as it’s owner. In our downtown shop or in the comfort of your office or home, we showcase the world’s finest fabrics – each ready to be custom made to fit you perfectly.

Our clients – men and women who seek and appreciate true quality – rely on our decades of experience and seasoned advice in making their wardrobe selections. Our hands-on tailors and “old-school” craftsmanship are unique in today’s market and bring added value to every garment we make.

From suits to shirts – business classic to luxury casual, the Richard Bennett garment flatters both the shape and the ego in the way it fits perfectly and reflects good taste and success.

Our mission? “Old fashioned” service, the finest custom clothing and happy, well-dressed customers for life!


COVID-19 Update

We have taken great care and consideration to modify the Richard Bennett experience to ensure the health and safety of our customers and staff.

  • “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.



Since 1929, we have been Chicago’s leading Custom Tailor – handcrafting garments of distinction – in our own downtown shop – for the area’s most discriminating men and women. Our approach is decidedly “old fashioned” – no offshore production or internet guesswork. Instead, we offer the sensible advice of seasoned clothing professionals and authentic, quality workmanship.

A pattern is created for each client by our staff – based on personal measurements and style preferences that are recorded in great detail. Multiple fittings with our hands-on tailors ensure a perfect delivery. Every garment is meticulously cut, sewn and finished to fit comfortably, wear well and look great!

Our in-house staff of European Master Tailors has over 200 years of combined experience in the pursuit of sartorial splendor. Nowhere in Chicago is this level of craftsmanship available to create a personal wardrobe. The result? Clothing of integrity that embodies the good taste and success of its owner.

Chicago's Most Recognized Tailor

  • Chicago Magazine

    Inside a Chicago shop that still makes suits completely by hand. Meet the craftspeople at Richard Bennett Custom Tailors & Shirtmakers who measure, cut, and stitch each garment the old-fashioned way.
  • Air Jordan Commercial Featuring Richard Bennett

    In 2017, Nike filmed the Air Jordan XX9 commercial starring Russell Westbrook – in Richard Bennett Custom Tailors store
  • City of Chicago TV

    City of Chicago TV spotlights Richard Bennett Custom Tailors and the unique way they approach their business.
  • Made In Chicago

    Richard Bennett Custom Tailors discusses their commitment to American made custom tailoring.


Experience a hand crafted custom garment for yourself. Make an appointment to meet with one of our staff members.

175 N. Franklin St.

175 N. Franklin St.
Chicago, Illinois 60606