The Best Tailor in Chicago

Paula Kay, the owner of Orleans Cleaners located at 636 N Orleans Street in Chicago’s River North neighborhood is the best tailor in Chicago. I'm naming the best tailor in downtown Chicago based on the extensive tailoring that has been provided to me over the last several years!

When I moved to Chicago over four years ago I spent a year trying out several different tailors in downtown Chicago. I initially found one that I really liked, but they were operating in a growth capacity. They were very expensive and their turnaround time became far too long for my “I need these in a week” mentality. So, I went searching again for a tailor that I thought could handle my tailoring needs and I gave my local dry cleaner a shot! Three years later and a number of tailored garments I don’t want to actually add up, I have remained 100% satisfied with Paula at Orleans Cleaners.


Growing and running a personal men’s fashion Instagram account with over 114,000 followers is an incredible opportunity to work with and photograph a lot of different brands. This also means that there is a lot of tailoring that takes place for the clothes to fit perfectly. Paula has tailored just about every type of men’s clothing for me and has basically become a consultant. I bring in new products for her to tailor and I always trust she’ll advise me on how the fabric might adjust as I wear it more and also the most cost effective way to achieve the looking I’m seeking to achieve. She even brings my complicated alterations home with her so she can have full concentration, thank you Paula!


One example of the consultation is when she was working on one of my many blazers. I needed the sleeves shortened in length a considerable amount. Since the blazer had functional buttonholes the sleeves have to be shortened by the seam on the shoulder, so the entire sleeve needs to be opened up. As she was marking the sleeves for the fitting I was complaining about the amount of padding also in the shoulder. After she did the fitting Paula said she was going to open up the shoulder while I was there and see if she could remove some padding. Sure enough, she was able to do this and was able to, which helped the jacket fit better overall! This is just one of several examples where Paula goes above and beyond.


Men’s pants and shirts are table stakes for Paula. She’s worked on suede jackets and heavy top coats for me where her true skill can really shine! She continues to tell me that

Women’s dresses are still way more complex than even my most complicated article of clothing. So, with that knowledge, my fiancee has started bringing all of her dresses to Paula! Each one has been successfully tailored!


If you’re looking for the best tailor in Chicago, then look no further, Paula Kay at Orleans Cleaners. Orleans Cleaners has been in the same location since 1994 and Paula does all of the alterations, so you can trust that you are in good hands! Paula learned the craft from her mother who, not only altered clothing, but would also turn her husband’s older clothes into new clothes for Paula!


I appreciate all the work she has done over the last several years and I wanted to give back to her and her family by writing an honest review. This post is NOT sponsored.



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