I dropped in last summer out of curiosity. I left with two new hats. I came back this summer, and had to get another one. Let's be clear: these are high-quality, high-end hats. They have an amazing selection, and refuse to rush you through the process of finding the right hat, continually offering to build the perfect hat if what you really want isn't right there. So now I have three of these hats and I'm already wondering which will be my fourth... PS - I've gotten three (3) compliments on my new hat (image below) in the past two days. read more

Optimo Hatmakers - The "Park Avenue" in blue pearl. - Hats Near Me - Chicago, Illinois

Had a shockingly bad experience at Optimo maybe it was an off day for them but looking at the negative reviews around the internet lined up with my experience exactly. I walk by Optimo fairly regularly and I had looked up their website and loved what I saw. With a rare day off from work with no other commitments I was excited to see the store and hear the hat lore. And buy a hat for myself and a gift for my dad. Unfortunately the person at Optimo was not as excited about me. As soon as I walked in the vibe was off she barely looked up from whatever it was she was doing to give me a lukewarm welcome and immediately go back to ignoring me. I asked about the store and the hats getting information was like pulling teeth. Then another customer walked in who she immediately began helping to ignore me. That was my cue to leave and idk if I will ever have a cue to come back. Which is fine because there are other custom hat makers contrary to what Optimo would have you believe. The hats were nice but at that price point I am expecting top notch service and Optimo is in the basement. read more

What a treat today walking into Optimo hat makers at 51 West Jackson. I thought I had stepped back in time and by the time I had a hat on my head, it was both a perfect fit, and a perfect style. A few months ago I noticed a sharp looking guy with the perfect fedora on in a Naperville Starbucks. Being a career retailer who has always fantasized about being able to pull off such a look, but never finding the right combination, I commented to him how sharp it looked. Ironically that man turned out to be Graham Thompson, one of the world's best hat makers and the founder of Optimo. Getting a quick tour today from his apprentice was even more impressive, seeing the molds and hearing their process to match hat, fabric, and brim style to head shape and desired look. It didn't surprise me after a few minutes of discussion, the first hat he put on my head was perfection. It's another one of those retail experiences you never forget, and one that could never be duplicated online. read more

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I wear hats, always have, since my youth in New York City. Getting dressed up, going to the "city," to a play, dinner, jazz club in the Village etc; I put on a Pierre Cardin suit, Chavret shirt with french cuffs, Oleg Cassini silk tie, Bostonian wing tips, and a fedora from Worth and Worth, and knew I was ready for a sophisticated night on the town. I was seventeen years old. Times changed, Kennedy went hatless at his inauguration, he was sadly assassinated, the Vietnam War broke out, demonstrations, the Beatles, drugs and jeans, all brought about a new casual tude towards everything. Hats became passé. Eventually, baseball caps became de rigour, but they're ugly and have no style. Baseball caps fit the need for homogeny demanded by the Technology Generation. I still wore hats, fedoras and panamas. Yet, decent hat stores have shuttered their doors across this nation. It was impossible to find a good hat store in Milwaukee, Louisville, and Salt Lake City. I depended on taking chances with an internet purchase, certainly a risky proposition. Then chance brought me to Optimo hats. I had no idea. On a cold, blustery windy April Chicago day, sleet pelting me from all angles, my hands shaking from the freeze, I used Google maps and put in "hats," while standing outside Bloomingdales on Michigan Avenue. Up popped Optimo Hats, almost a 2 mile walk south in the Loop. I wasn't in the mood for The Museum of Contemporary Art, and liked the challenge of an urban walk in the beastly conditions. Thus, head bent against the wind and frozen pellets, I began my "frozen tundra" walk to Chicago's political apex, passing the Water Tower, over the river, the Goodman Theater, the infamous Picasso sculpture, the lost Chagall mosaic, until I found Optimo. Expecting an old school, inner city, hat shop, I was surprised and almost bewildered to find a bespoke, elegant men's hat emporium. What was it doing within sound and sight of the elevated train? Who cared, I was in hat heaven. Optimo makes its own hats in their factory a few miles away from their shop. Alexander, a young man reminiscent of the tailors fitting you for a custom suit on Savile Row in London, helped me try on a few Panama summer hats. Nothing made me want to spend the minimum $500 on the cheapest, even if the hats are so well made. Then, Alexander walked into the back room and brought out the "hat." It was it. The hat I imagined myself wearing on a cruise down the Nile, boarding a Vaporetto in Venice, listening to Chick Corea in Aspen, drinking a chilled glass of white wine in Palermo Soho down Argentina way, and even strolling Main Street in Salt Lake City, pissing off 90% of the people who place demands on humanity to fit in, never stepping outside the lines prescribed by the hierarchy. The hat was me and will be mine. Money well spent on something that can stretch the imagination, taking me to places I rather be. Optimo Hats transported my soul. Thank you. read more

If you have NEVER had a custom-made pure beaver fedora, cowboy or porkpie hat made, you are in for a treat. Much better than the ready-made. off the rack variety you can get at a quarter of the price, and if you're a hat guy like me, it's a nice indulgence. If you HAVE had hats made for you, as I have had may times, this is a very nice hat, but not one of the top 2 or 3 custom jobs that I own. Good people, and a perfectly good product. read more

I bought a hat yesterday here. This place is wonderful, the attention to detail was unparalleled. I got fitted, chose the perfect style and color. I am a traditionalist, and the hat finishes the outfit. I never felt pushed or rushed. I emailed them first and talked to the manager, and she was so nice, I could not wait to meet her, and the wait was worth it. The worst part, is now I want to go back and get another hat........ read more

I just received my new Homburg hat from Optimo Hats. This is my 11th hat from Optimo, and they just keep getting better...if that's even possible. It is butter soft and fits like a dream. I can't praise Optimo Hats enough. Very well done Graham and team! Hats off to Optimo! read more

Optimo Hatmakers - Beautiful rich color combination... - Hats Near Me - Chicago, Illinois

I just got my hat in the mail today and I love it. This is a place where they measure you head and then custom make your hat to ensure that it fits. I have a pretty big head, so I don't have many options in the hat department, but I'm glad that Optimo is there to keep me looking good topside. I hope to go back and get a Panama hat someday. The hats can be pricey, but you can also get a standard grey felt fedora for about $650 (which is what you really need). read more

Optimo Hatmakers - Best mail I've received in quite a while. - Hats Near Me - Chicago, Illinois

Superior. That's the word that captures the quality and service at Optimo. Graham is on a quest to make the best hats in the world. I own several of them. read more

Optimo Hatmakers - Graham always takes care of my hat needs. - Hats Near Me - Chicago, Illinois

I was one that was convinced I cold never pull a hat off. These days any brim width and crown height seems too attention-grabbing at first. Even my wife probably wanted to leave me when she first saw it on me. But now it's my signature look and my wife couldn't like it more. I made the hats mine, but they've also come to distinguish me aesthetically. Optimo has stunning hats, quality, store space, and service. They're the best hat maker in the world. The best window shopping in Chicago. And have the store smell anywhere (from the old hat blocking materials and straw hat sulfur). The beaver felt hats will last a lifetime, and authentic "panama" Ecuadorian Montecristi straw hats can as well. The straw weaves are absolutely breathtaking. Some may balk at $1000+ for a hat. Let them wear the polyester ball caps, itchy wool beanies, and cheap paper straw hats. Better for you. You 'get' it once you have it, and realize what a ripoff any other hat is at any price. Every penny invested in an Optimo seems to be a steal, and the secret only you and the other clients are in on. If you live in a place like Chicago, where rain and snow only occur horizontally, part of your unconscious has already been telling you for quite some time that there is a better way than all those broken umbrellas and rain-plastered eyeglasses. Invest in a good trench, and a beaver felt Optimo, never looking back. And if you've ever enjoyed a special moment in the summer sun, that kind of moment which seems frozen in time, serene, in that special mental drawer of emotional and tactile richness... that's the feeling you're present to all Summer in an Optimo Montecristi. Tiffani, Alexander, the tailors/attendants are great at contextualizing hat traits in meaningful ways to help you understand what you do and don't want regarding height, width, shape, color, ribbon, etc. They have some to sell and try off the rack, and you can order custom. There are formal hats, adventure hats, practical hats, golf hats, blues hats, posh hats, and all of a quality that represents the best there ever has been. If you ever run into the owners at the shop, you quickly realize that they are both expert connoisseurs and down-to-earth Chicagoans who 'get' hats at the global-local, contemporary-historical, musical, practical and poetic levels. And all of that has already gone into the curating of the hats. Life's better in a great hat. But an Optimo hat is a rich overindulgence one seems to breath in and bathe in whenever they're lucky enough to don it. My Optimo hats are my favorite things. read more

Just picked up my favorite straw hat after having it rehabbed at Optimo Hatmakers. it looks as good as new! I love that they make their hats here in Chicago. Many thanks to my wife for the gift of my first custom made hat 10 years ago. If you're interested in heirloom quality made by true craftsmen, then Optimo is a great choice. read more

Every time we visit a new city, my (now) husband has to purchase a hat. So while in Chicago last year, we strolled around and found Optimo. From the second you walk in, you realize the exceptional craftsmanship on every hat in the shop. Unfortunately at that time, we couldn't afford the investment and sadly left empty handed. That night we got engaged, and ever since then, my guy continued to speak about the optimo hats he had tried on. 'Beaver pelt! I need a beaver pelt hat' I knew this had to be his wedding gift, it was the perfect opportunity. This passed August, I reached out to optimo and spoke with Tiffani, who I remember speaking to when we were physically in the shop. She was such a great help with my secret gift, even marking the shipping label as a different company so my beau wouldn't realize! When I gave him his gift on our wedding day, he was over the moon! He had to wear it for the wedding reception! It was worth it all!! Thanks optimo for existing and being the best hat shop i've ever been to! read more

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Beautiful store. Great selection of very fine hats. Friendly, very competent staff...Alexander was very accommodating. read more

Optimo Hatmakers - Inviting! - Hats Near Me - Chicago, Illinois

Hands down the best hatmaker in the world. You are not buying a hat, you are buying a piece of art. Graham Thompson and his staff are the best. read more

The world's best hats, I had a business trip to San Francisco, so I decided to extend it a couple of days and head over to Chicago to check the hats out. They are the best made hats. I live in Sydney, bought one and can't wait till it arrives back in Sydney. read more

Optimo Hatmakers - They take extra care to fit your hat - Hats Near Me - Chicago, Illinois

Optimo Hats are a great value, IMHO. Up front, yes, they are expensive, no argument there. But the fit, the material, the craftsmanship, all are beyond expectations. A Borsalino might be cheaper, but it's not as durable. An Optimo lasts a lifetime. In my case my hats will last longer. With my life expectancy, (age 96 according to the IRS!), I realized that I should rewrite my last will and testament. So, I sent word out to my six brothers, and found one with my hat size. This means that in maybe 25 years, my Optimo Hats will be going to Eugene, Oregon. I expect these hats to outlive my brother as well. You add up the cost of a new Borsalino every couple years, and the Optimo turns out to be a pretty good investment. read more

I have a Fedora from Optimo. It's made by hand on old-school equipment the same way hats were made back when a man wouldn't be caught dead without a hat on his head outdoors. All the hats are made-to-order specifically for each customer. The staff is amazing. Tiff will get you set up with a hat that looks great and looks great on you, and she'll tell you in no uncertain terms when you look ridiculous. And trust her. This isn't her first rodeo. It wasn't an hour after I left the store with my hat on that I got my first (first of oh-so-many) compliments on the hat. The hats may seem crazy expensive, but they're crazy good and you're paying for hand-made-to-order quality. A TON of work goes into these hats, by people who care about hat-making and about their customers. You're going to make an investment here, and these are hats that you're going to be wearing until you pass them on to your grandkids. I've already got two invoices written up ready to have my next two hats custom made. Every time I'm in Chicago I make it a point to stop in. read more

If you want the best made hat in the world, this is the place. $500 to $10,000+. Perfect fit- exact consruction. So many styles--so many fabrics and colors. read more

Had an awesome experience here! Their hats are extremely high quality. You pay for it, but it will last a lifetime. Tiffani was especially helpful and got my husband hooked up with a really sharp hat. Extra stars for the friendly service, handwritten note, and quick replies to questions via email. read more

Today I received my first hat from Optimo Fine Hats and was sincerely blown away. The quality of these hats are simply "Top Shelf". Word to the wise these are not your bargain basement run of the mill varieties, they are custom in every way. Let's just say when you put on a hat from Optimo you feel like man who should be making decisions. :-) read more

I purchased a charcoal club fedora a few months ago and it is one if the finest hats ever made. The staff was very helpful and knowledgable and the owner is world class. The products are worth every penny and they have gained a life long customer. read more

This was a fun place to visit. Great customer service. I have never been fitted for a hat. Was similar to Harry Potter getting his first wand. The girl looked at my head and went to all the hats she had and put it on my head. Best fit I have ever felt in my big head. Looked good too! The bad news...with service and fit comes the price. Cheapest had here is about $500.00. The one I tried was 750. We did not buy a hat, but if you are in Chicago it is a fun stop. read more

I have been wearing my new Optimo hat for one week now. I adore it. I own custom hats made in Montana, Borsolino hats and such. I can unequivocally say that my Optimo chapeau is the finest topper I have ever seen. The staff at the store is expert, friendly and laid back (not pushy.) They are proud of their products and they should be. These things aren't cheap, but boy they are worth every penny. read more

I have purchased two hats from Optimo. I have hats from Stetson (the good one made from beaver felt), Akubra, Borsalino, and Locke, and Optimo distinctly exceeds them all. The appearance and feel of the felt is sublime and the fit is exactly right. Both of the two I bought, Elk and blue pearl, are darker by a lot than they appear on the website. The darker colors work just fine for me, and this is in no way a reduction of quality or a complaint, but the buyer should consider that when choosing which color will work best for their purposes. read more

This place has yet to fail us. The staff here will take time to find the perfect hat for you. They actively take a chunk out of their day to find a hat that suits you and your needs. If you are looking for a great hat place, stop in because they will cater to your hat related needs. read more

I am addiicted to Optimo's hats. I own three and three more are on their way. I wear them around the house, and stare at myself on tthe mirror as I walk by. They are jewelry, really. read more

I love my hats. (Yes, women can get hats there too.) I have two and they are the best splurge purchases I have ever made. I get compliments on my hats all the day. read more