Men’s Custom Tailor in Chicago

Who can deny the appeal and statement of a well-dressed man in a custom-tailored suit?


When handmade and fit properly by master tailors, the custom suit or jacket is every man’s best garment. Delivering that garment is the essence of Richard Bennett Custom Tailors.

Uncommon Design

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.


We have been hand-crafting the finest suits, jackets, formal wear, trousers, vests and overcoats for the most discriminating clientele for nearly 100 years.

Ours are the garments you have been waiting to wear

Chicago's finest custom tailor since 1929 has been featured in

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Client Stories

Every garment is designed just for you! Read about how Richard Bennett has handcrafted solutions for these clients to see how the right fit looks and feels great.

Wedding Tux Tailor Chicago, IL

See the latest Client Story for Pete Zervakis.

A television news anchor and reporter, Pete understands how important appearance is to his success and places a high value on wardrobe.

Explore the possibilities and we look forward to being of service

Happy Customers

Nothing but the best experience

“Top flight shop! Cathy M knows her stuff and RB ensures your experience is all about what you want it to be! Zero pressure, helpful guidance, and nothing but the best experience. “
Ross M.

William took care of me in an entirely professional manner

“William took care of me in an entirely professional manner that still made the experience fun. I ordered two pairs of pants initially, and after seeing the fit and the quality of the work, have now ordered two more, plus a suit.”
Brian T.

My go-to tailor in Chicago

“RBCT has become my go-to tailor in Chicago. Conveniently located and unbeatable in terms of both quality and customer service. A real classic place that makes you feel proud to be a Chicagoan.”
Jacob W.

The details are where this small shop excels

“The quality of the hand-stitched button holes, the precision of the pressing, the evenness of the stitching in the seams – it is the details of construction which truly set the bespoke garment apart. The details are where this small shop excels.”
Scott P.

I'd recommend them to anybody

“I’d recommend them to anybody. The location is super-convenient for me, but even if I moved offices I would go out of my way to stop by Richard Bennett.”
Alex K.

Richard Bennett's customer service is exceptional

“I’ve just been back for some more (of my new favorite) pants, and suffice it to say, Richard Bennett’s customer service is exceptional. I’ve been in only a couple times now, but I’m always greeted by name. Definitely an atmosphere that makes me want to go back, never mind the sensational product.”
Andrew T.

Do yourself a favor and upgrade

“The price was also a pleasant surprise. I have purchased off the rack at Saks and Nordstrom for more, without the custom fit. If you shop at those stores, do yourself a favor and upgrade. You will be glad that you did.”
Brian T.

I'm definitely going there before buying off the rack again

“I walked out with an excellent suit that fits perfectly. This despite my bizarre body shape, and for less than I thought it would cost. Everyone at the shop was helpful and courteous, and I’m definitely going there before buying off the rack again.”
Brian M.

You will have a blast, learn a lot, and have a product that will last for years

“Do not try to rush the process. This is a small shop – not a factory front. Bespoke is not like made-to-measure. If you approach the process with factory expectations you are setting yourself up for frustration. Approach this as an experience of working with a team of artisans in creating a wearable work of art, and you will have a blast, learn a lot, and have a product that will last for years.”
Scott P

What a difference

“These guys are great. I had my first made-to-measure suit built for me recently after having two done at [another custom tailor]. What a difference. They use similar materials but the difference in quality is apparent from the beginning.”
Michael H.

Never will I buy off the rack again

“Never will I buy off the rack again. When something fits right, you want more.”
Ron M.

Recommend to all

“I was greeted by first name upon my return which is impressive given the spelling of my name. When dealing with pricing, they are on the higher end but it goes hand-in-hand with their quality of work and service. Recommend to all.”
Irbad C.

I have been back multiple times

“I have ordered several suits and a bunch of shirts here. I have been back multiple times. They always remember my name, and the service is what you would expect for a custom shop. The prices are fair – not cheap – but that is what you should expect for custom clothing. Overall a great experience.”
Rick M.

The workmanship is impeccable

“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.

The Highest Quality Fabric

At Richard Bennett Custom Tailors, we believe that a well-made suit is more than just a piece of clothing – it's a statement of confidence, style, and success. That's why we are dedicated to providing our clients with the highest quality, custom-made suits tailored to their individual needs and preferences. From the initial consultation to the final fitting, our team of experts is committed to ensuring that every aspect of the process is tailored to meet your needs. If you're ready to experience the difference a custom-made suit can make, contact us to schedule your appointment. We look forward to helping you look and feel your absolute best.

We look forward to being of service