Optimo hats, Chicago

Wednesday, December 12th 2018
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Optimo is everything you might want from a craft manufacturer.

There was a passionate beginning; a long gestation; success and popularity; and now a beautiful new factory that supports transmission of the craft. Plus a product that is superlative quality, and rather distinctive. 

I had been aware of Optimo for several years, but as they're in Chicago, it was hard to find the excuse to visit.

Fortunately, owner Graham Thompson (below) was visiting New York for a trunk show when I was there, so I took the opportunity to meet him and try the hats.

Graham (pronounced, in the American way, 'Gram’) was obsessed with hats from an early age: particularly those worn by Hollywood actors in the 1930s and 1940s.

He was a regular at one of Chicago’s best-known hat shops - Johnny’s - when he was young. But the year Graham returned home from college, he was shocked to find out Johnny’s was closing.

After a few conversations, Graham changed his entire career plan, agreeing to buy Johnny’s business and continue the legacy of hatmaking in the city.

There’s a lovely video of that process on the excellent Optimo site here.

Graham set up Optimo when he was 22. Johnny was officially retired, but continued to work there and teach Graham - pretty much up until his sad passing, seven years later.

Today, after 25 years, not only is the business sustainable but Graham was able to buy, and entirely restore, an old fire station to construct a new workshop (pictured above and below). It opened in 2017.

The factory looks beautiful. Functional and efficient, yet steeped in history, with a mix of old and new blocks and machinery.

I’m determined to visit next year.

When Graham and I met, it quickly became apparent that not only does he look good in hats, but (more importantly) he understands how other people can look good in them - and why they think they don't.

If you want to read more on the subject, I've written about hat look and fit here.

For now, suffice it to say that I think pretty much all men can look great in a hat. They just need to understand what style suits them, and ideally have a retailer that can demonstrate it.

Optimo makes fur-felt dress hats and panamas - there are no stiff Western models, or modern designs with odd finishes and matchsticks stuck in them.

But within that, there is a big range of materials, models and constructions. And Graham understands which of those will suit different people’s style and face shape.

The model on me below, for example, looks great from the side - it's a clean continuation of the shape of my head - but from the front it's a little too square, and could do with being more tapered.

Interestingly, when Graham trained under Johnny the shop repaired others’ hats as well as making their own. This gave him a useful overview of the rest of the market - at least in North America.

It was fairly easy, then, to pick the materials and production methods that produced the very best hat - in his experience.

In terms of production, that included things like double blocking, or decatising. Basically going through the blocking process on every hat twice, in order to set the shape more precisely and giving it more longevity.

For materials, it meant using largely beaver felt, with the occasional push into even finer felts, like beaver belly or mink.

Cheap hats (most of the market) are made of wool. Decent hats are made of fur felt, the majority farmed rabbits. Better hats are made wild hare felt, and beaver. Optimo uses the very best beaver.

("Saying it's beaver in hatmaking is like saying it's cashmere in knitwear - there's still a lot of variation," says Graham)

Actually, the thing that surprised me most about seeing the Optimo hats in person was the felts.

They were stiff, yet malleable and light. They felt strong, and Graham demonstrated how they could be crushed or moulded and then re-shaped.

They felt distinct from felts I've used with any other hatmaker.

It’s mostly about density, apparently. Modern hats use less-dense felts because it’s thought people want something more malleable and soft.

But those quickly lose their shape over time. Indeed, they aren’t even more malleable, really, because they can’t be shaped by the wearer to a look they want.

If you try to put a certain crease in such a hat, it will just drop out over time or when it gets wet. A denser beaver felt is easier to shape, and re-shape, with perfect control. 

There’s more on felts and production on the Hatmakers section of the Optimo website here.

I ordered a fedora from Graham in a very dark brown/grey felt (above).

Slightly tapered crown for my narrow face; decent size of brim as I can get away with it, being tall.

Standard beaver (for them) with a smooth finish. Much as I like the fluffy finish of my Stephen Temkin hat, I wouldn’t want it on every hat I own.

Ribbon in a grey to keep it formal (it’s amazing what difference the ribbon colour can make to the colour you think the felt is). Graham has new ribbons and thousands of metres of vintage ones bought from old hat shops.

And a welted finish on the edge, where it is simply folded down and stitched (below). Most brims are either welted, bound, or left raw.

A welted edge is sturdy and stronger than the others, but isn't necessarily more casual or formal, according to Graham. Dress hats and sports hats have been made in all three finishes at different points.

Optimo hats are not available to buy online.

Even in the shop in Chicago, a customer cannot simply walk in and pick up a hat. In Graham's view interaction is fundamental, and therefore a customer has to request a hat from behind glass to try, which then comes with certain advice.

However, a reader can arrange a phone appointment with someone from Optimo (details here), which will involve a discussion of styles, lifestyle, and a self-measuring of the head (video on that here).

And after a long resistance, there will be some selling online with Optimo's new website, launching soon. But only for repeat customers.

Most hats are ready-to-wear and sold as such.

Fit is not that hard with hats, after all, and Optimo does sizes in half centimetres (which is very unusual) and in at least three different shapes: round, round oval and long oval (me).

Custom orders like mine make up about 25% of sales, and are usually when someone wants a different brim/crown combination - or unusual colour.

The ready-made styles can be seen on the Optimo site, here.

I'll report back on the finished hat soon. In the meantime, thank you to Graham, to Edmund, and to Steven at Leffot for hosting us.

Photography: Elliot Hammer

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The hats don’t do much for me (I’ve got a couple of watch caps from Drake’s that serve all my head covering needs) but what an amazing looking shop!

Chin-Chen Lee

How would this compare to offering in London (say Lock & Co)

Peter O

1. What do you mean by hard to find an excuse to visit Chicago?
2. Did you mean Graham’s hats are a higher level of quality than Locke’s?
I’m surprised, because Locke’s claims to be the best.
3. I don’t understand your phonetically observation. Graham is not usually pronounced in Chicago as
Gram (one syllable), but with two:
Graham = Grey + hM. Make a test.
For example: Graham Crackers.
4. Did you ask Graham how he came to use this particular felt?
5. You look cool wearing a hat, Simon.


Great to see more on hats, as it is something as I am lost on what I should be looking for in hats!

I’m wondering how the stiffness of the felt with Optimo compares to Leon Drexler. Was Leon Drexler’s soft and flexible like most other hat manufacturers? Or is it closer to Optimo’s?


I would recommend a visit to Chicago. As cosmopolitan as NYC sans NYC brashness. And that dramatic skyline surpasses anything NYC can conjure up.

Just avoid Jan-Feb due to the typically brutal cold.

Peter O

PS: Neither Obama nor University of “Chicago” are native to Chicago. Obama and Rockefeller instrumentalized the city. Obama lives in a villa and University of “Chicago” is
a Rockefeller elitist experimental station.

Peter O

I disagree with G regarding comparison of New York and Chicago. New York is for a Chicagoan for more complicated.
Chicagoans respect New York because it has more history and is
not as easy to comprehend as Chicago. NY is under influence of Europe. Chicago has organization and is the right place to get things done. In every sphere Chicago is organized, for good and evil. Lake Michigan gives the flatland freshness and flexibility. Chicago is not cosmopolitan. It is itself. Chicagoan would never consider NYC brash. Chicagoans admire NYC in many respects. Now you have your own peacoat to keep warm, but weather in Chicago has many temperatures.

Stephen C.

Whoever Peter O. is, he is correct in all of his observations about Chicago. I was born in Chicago and reared in its N.W. suburbs but do not consider myself “of” Chicago, but perhaps really an international-cosmopolitan with huge respect for New York and other places like Switzerland, where I have had clients. Chicago, with its amazing location and vast airport, lets you go anywhere fast and get there & back with ease. A lot of things are easier in Chicago (some not, like road traffic & parking) but we don’t make a big deal of things here — including the dramatic weather. It always puzzled me that suburban people scorned the City of Chicago. As a business-owner, my family & I were always in-and-out of Downtown/The Loop using our fantastic commuter-rail lines. Today, I can go to L.A. using Amtrak by driving three miles; parking for seven days at a meter in Glenview; and taking the Hiawatha service to Chicago and the Chief to California, totally bypassing the TSA-experience at O’Hare. Yes, it takes two days — but you ride through New Mexico and actually see it, in the company of convivial people. Chicago abounds in those kind of people, also. And those hats at Optimo? Let me at-’em, Brother. As for Gramm or Gray-em? Whatever. When I speak, people always ask if I am from London.

Peter O

Dear Steve,

When Simon studies a map of Chicago, he’ll see the transparent Burnham post-fire street coordinate system and need to ask where the two huge Afro-American ghettos are (on the South and West Sides). Your comment about the Chicago suburbs and their relationship to the city (not to be confused with such an oddity as so-called independent corporation “City of London”)
is justified. Please keep in mind the significance of fresh-water Lake Michigan whose expanse means its horizon is only water. So the suburbs beyond the North Side are connected to the city of Chicago by the shore of Lake Michigan and Lake Shore Drive and Sheridan Road.



Great piece on amazing hat makers.
I walked in there by accident about 2 years ago, and couldn’t phathom spending $750+ on a hat….fast forward 2 years and I’m about 8-9 hats in.
They are absolutely amazing quality, the fit and style are second to none.

Coming to Chicago next year?

That’s the most exciting part for me!

Anything big planned?

Andrew Eckhardt

Excellent news! Looking forward to popping down to Chicago to say hello. Please do keep us informed.

Reuven Lax

Same happened to me! Seemed like a lot for a hat, but I have no regrets 🙂


Christys of London also make some nice fur felt hats. They make them for Bates and Lock, too. Bates and Lock no longer make their own hats. Most of Christys hats are still handmade, in the traditional way, in Oxford. All three hatters have shops in the Jermyn Street area of London. Just to complicate matters, Christys are owned by Liberty. If you live in the UK and want a fedora or a trilby, Christys are a good company to consider and they are a pleasure to deal with. They make panamas and a range of other hats, too.


When you’re next in Naples take a short trip to Salerno.. there’s a very good hat maker there, Russo Giosue. I’ve bought a panama and a fedora from him and have been delighted with both.


My city! A good shop for hats. Completely agree with you Thorn.

Reuven Lax

I own two hats from Optimo, and a number of vintage (deadstock, previously unworn) hats from from the 1930s and 1940s. The felt quality you describe is quite typical in these old, vintage hats. In fact while the Optimo felts are some of the closest I’ve seen to these vintage felts, the old felts are even moreso malleable and dense.

I believe one of the issues is a paucity of felt makers. 80 years ago there were many hat makers and felt makers, and a lot of competition for quality. Nowadays there are few hat makers and even fewer felt makers. In addition, some of the old old hat makers were vertically integrated. One prized edge finish (most commonly called the Cavanagh edge, but sometimes went by different names) looked like an underwelt, but without the brim being folded and sewn; the swelling was built into the the felt itself. This is something that required coordination between the felt maker and the hatter and no modern hatter is able to duplicate it.

That being said, while the quality of some of the old hats is unbeatable, modern craft manufacturers have a special place in my heart, and Optimo is one of the best.


I like fedora hats. But myself I am stopped by three issues:
1. I am affraid of looking way too dated. As if I am going to a costume party.
2. I am short and I am not convinced that a fedora hat is a good thing for a short guy.
3. How do you drive a convertible without the risk that the hat goes off your head. Even if you have it connected to your buttonhole, it would still cause a distraction if it happens.

Andrew Poupart

1. Why would you be afraid of looking dated? That feeling doesn’t make sense. Think of a hat as a useful tool for protecting your head from the sun and the elements.
2. Perhaps another style would work best for you?
3. Don’t wear a Fedora in a convertible. I drive a vintage 450SL and only ever wear caps when driving. Linen in summer, tweed in winter.


Hello Andy,

it is impossible to walk 100 meters in Munich in a fedora hat without gathering the attention of everybody around. Attention is not necessarily a bad thing, but in this case people are not thinking “what a great style” but are thinking “is somebody shooting a video clip about the 40s/if I am going to a costume party”.
I think you are both right, that I have to check for a good hat maker/shop that could do a proper consultation on the style and shape that could work for me.
Regarding a driving caps. I am interested, but is it really safe to drive with it?

Andrew Poupart

Hi Hristo,

People stare at me in the States, and in London, too. It doesn’t bother me in the slightest. I don’t necessarily agree with Simon’s point about wearing a hat “subtly”. I’m not sure how one could really do that. It feels like an apology, almost. Better to wear an appropriate hat and feel good in it.

Regarding driving caps, I’ve had no problems at all with either linen or tweed at speeds up to 70mph or so. I wouldn’t try going much faster than that in a convertible wearing a hat, at least not in my car. Try it and see if it works for you!


THank you, Andy! You are right, I should give hats another try.


An excellent way to ease the process is to wear appropriate hats in the pouring rain. People will gaze at you with envy.


@Simon: Could you recommend a place to order a cap in Europe (Germany, Italy, France, UK)?

@Andy: You could definitely post some more photos with a driving cap.
I only found a photo of the white linen one:


Thank you!

Clifford Hall

Simon, be interested in your thoughts on what you are planning on wearing with your new hat when the time comes. Have a similar custom hat and always looking for inspiration.



If there is a better hat than Optimo being made somewhere on the planet then I have never come across it on my travels – they really are an heirloom item that can be worn daily and still passed on to the next generation

Andrew Poupart

Very nice piece, Simon. I wear a hat every day and Optimo had been on my list of must-visit places for several years. I finally got to visit the store about a month ago. What an amazing place! You really will enjoy the visit. Adding to the pleasure, the shop is located in one of Chicago’s 1930s buildings.

I bought two hats on my visit and have since bought another one by email. The quality is virtually unmatched. Only a completely custom, handmade fedora I have comes close. I’ve been a customer of Bates’ for years but I may go to Optimo for all my future hat needs.

Your hat looks like their Park Avenue model, am I right? If so, it’s one of the hats I purchased from the store. Mine is light grey, in undyed silver belly beaver, a very versatile color. Since I bought it, it has become my most-worn hat and was the only hat I brought with me when I visited London last week.

Anyway, excellent piece!


Optimo hats look to be superb and what a fabulous factory.
Although I love Chicago, it’s a bit off the beaten track – does he do trunk shows and how would you avoid import tariffs on hats shipped to the U.K. ?
Great article – this is what PS is about.


Hi Simon.

At what age should a man start commissioning a bespoke suit?



I do very much hope you are able to come and do some sort of event here in Chicago, especially if in conjunction with Leffot and Optimo. If you do end up coming to Chicago, also consider seeing the Horween tannery (cordovan, among others). I know Kirby Allison went over the summer



As a rule of thumb, wider brimmed hats, such as the fedora, suit taller men. Narrow brimmed hats, such as the ‘stingy brim’ trilby (or just a trilby) suit shorter men. My view is that the pork pie hat suits no one – not even jazz players.

However, the trilby hat comes in a range of shapes. While I have a lot of fedoras, I find a medium brim trilby the ‘easiest to wear’. Coloured fedoras can slip into the ‘costume’ look. The really important thing about hats is to feel comfortable in them. Or, ‘put the hat on and then forget it’.


“Bogart” the consummate hat wearer was 5’8 – perhaps the exception that proves the rule?

I like the old 30’s & ’40’s films and everybody wears a hat. Where did they all go?

Also, when and why did the baseball hat become the thing to wear? It really isn’t better!

Toby Luper

Thanks Simon…..I love hats….my oldest hat is one from Lock & Co which my late brother, John purchased for me 42 years ago for my birthday and it still looks great today!
I will certainly be making a visit to see this shop in March when I’m next in Chicago seeing my tailoring clients over there!

Barry Jaynes

Love your website and mailings. Surprised to see Gram using tape measure to measure your head. Fifteen years ago he did the same for my head at Wilkes Bashford. Wonderful hat…alas it did not fit! I have number of custom made beaver hats,($1,000- 2,000) that fit perfectly. In each case a conformateur
was used for the head measurement. I will not purchase a custom hat unless
a conformateur is used.



A nice hat but I think the fur it’s made from would have looked better on its original owner. Provenance goes back beyond the maker to the source of the original material, in this case a wild beaver. A hundred years ago, beavers were nearly driven to extinction by the fur trade and although numbers have recovered, over 135,000 are killed each year in Canada alone. At a time when global wildlife is coming under sustained threat from habitat loss and climate change, we surely have a duty to protect it and not add further pressures in pursuit of our insatiable drive for conspicuous consumption.

Elsewhere, you rightly rail against the unsustainable trade in cheap Christmas jumpers. You write: “There are many problems with consumerism and how it affects our planet, and society.” But the luxury end of the fashion market is also guilty of unsustainable practices and turning a blind eye to the source of its materials. As someone who buys good quality clothes, because they last, and who values your blog as a trusted guide, I would like you to pay as much attention to the provenance of the raw material as you do to the quality of the workmanship that goes into the making of the finished product.



Well said.

On a related matter, there are few cars I would buy that I cannot afford but almost without exception they come with dead animal skin interiors. As a consequence, I own a very fine Skoda with fabric seats and the “luxury” brands who use the conceit that leather equates to luxury and that their products are somehow artisinal in nature as a consequence lose business. This applies to any such vendor such as the one highlighted here. And then they wonder why they go out of business.

Get with the programme chaps – as they say in the colonies.


Really enjoyed this, thanks.

How would the quality compare to a bespoke offering from Herbert Johnson? I was in there a few days back back & was told that all hats are still handmade in England from the finest materials. The trilby’s looked & felt incredible

At around £500, not on the cheap side but understandable when you see them in person


Thanks Simon.

I should say that I’m not a fur campaigner but I am a conservationist. I think that biodiversity decline is the defining issue of our time and the one that future generations will judge us by. I know that only a small amount of fur goes into producing each hat but if the total use by the fashion industry adds up to 135,000 beavers in Canada alone, that is not sustainable. But I agree with you that the dumping of fur, for whatever reason, is a travesty. So what about recycling all those abandoned fur coats, like the one hanging in my mother’s wardrobe, into new hats? Worth asking.

Jeffrey Landis

Graham makes awesome hats.
Go to his south-side shop to get the full body experience. Very cool.



They are fantastic, I had a couple when I was a child – believe it or not, one in black Persian Lamb….

(Simon, as others have commented, you look sharp in the ones in this article…)

I have several hats, and wear them regularly – great for the skin (sun damage protection) as well as being stylish…

However, having inherited a fantastic Borsalino from my Dad, the biggest problem, is finding someone who can properly “block” and shape it…a lost art, sadly…even a lot of shops that retail them, have no idea where you can send them….

Does Graham have any suggestions?


Ciao Simon,

Been following your site for quite a while now – it’s really a fantastic read! As slowly building a wardrobe, I’ve particularly enjoyed all the capsule collection posts (trousers, shirts, etc.) – looking forward to more of those!

I have a question about your general experience with trying to find a hat. I am the ‘proud owner’ of a long oval head shape as well (there seems to be very few of us), and I’ve found that finding something that suits is an absolute nightmare (other than flat caps). I’m not feeling quite ready to make the jump to a bespoke commission just yet, but I’d like to start with something of decent quality. Trilbies usually look best on me (I am shorter, so the narrower brim is more flattering), but I just can’t seem to find anything blocked in a ‘true’ LO shape anywhere I go. Whatever I get pointed to in hat shops always ends up looking absolutely huge on me (the crowns are just too large since I need to go up in sizes). Even more frustrating is the shocking apparent incompetence of shop owners at providing any real guidance (maybe it’s a cultural thing as I live in France, but I always get blank looks when mentioning Long Oval, and sometimes just end up getting pointed to ridiculous things, ie: “oh, try a cowboy styled hat, that’ll work with your head shape”). So the questions are – how did you manage to find a ‘first hat’ that looked ‘good enough’ without going bespoke? Did you ever have any luck with more ‘standard’ retailers that don’t seem to offer dedicated LO blocked hats, ie: Lock&Co, Christy’s, etc.? Looking back on your first purchases, how do the fits compare to your current bespoke commissions?

Thanks a ton!


Most enjoyable post, Simon, thank you. Truly great hats, and Graham Thompson is as convivial as he is knowledgable. A visit to Optimo’s website will also reveal a good-looking Milan straw that has a wonderful golden color, a hard-to-find summer option.

As an aside, Optimo’s downtown Chicago location is in the Monadnock Building, a national landmark and worth a visit on its own. Dating from 1891, it is among the earliest skyscrapers in the United States, and per Wikipedia, the tallest load-bearing brick building ever constructed.

Great hats in a great building…..


I am sure that Optimo hats are good. But they are enormously expensive and mostly ready made. Can anyone comment on their value in comparison with the smaller, custom hat
shops that now dot America. I am particularly interested in a comparison with Vintage
Silhouettes in Oregon.

David Vizzini

Very good and comprehensive article. I ‘m curious, does this company use the same exquisite rabbit fur as that which was use by Borsalino for decades? I’m fortunate to have a collection of pristine, never-worn Borsalinos fron the 40’s to the ’60’s. Borsalino itself admits that they do not maintain the same quality as once was the case. Thank for any comments.


Any thought given to the conditions and methods the fur is “taken” from the unfortunate animals?


I must have missed it in the article.

There was a review of a long established maker of fine, hand crafted gentlemen’s wallets perhaps here or on a comparable site. In reading their website they source the leather for their wallets from Bangladesh. Now there are two things about Bangladesh leather, one that it is obviously the cheapest and two is the non-existent animal welfare and the appalling cruelty inflicted on animals there included skinning calf’s alive in front of their mother.

Needless to say no one should buy this company’s products and unless any company who produces or sells such items states the source of their materials I simply avoid them. I also think it is incumbent on web sites that review their products to enquire and remark upon into this aspect.

Mr. Pink

Though I’ve been in their shop, I don’t own any hats from Optimo. I do own a couple from Art Fawcett/VintageSilhouettes. I’d say the quality is identical. I’d recommend Art very highly. There’s a great deal of information about Art’s and Optimo hats at thefedoralounge.com. Also, Art will clean, reblock, or rebuilt vintage hats. Optimo used to do this but will only deal with their own product now.

Tim Fleming

I was so happy to see and read this post. Thank you Simon for your continued valuable content. I’ve been looking forward to the day when I can get an Optimo hat and hope to do so soon. Seeing this new factory and reading your input on the quality level and its position in the hat market only makes it more confirming of what I’ve thought and encouraging to go through with a purchase.

For the other gentleman who questioned wearing a hat due to being short, I’m only 5’7” and generally feel comfortable in a trilby, but I imagine my tastes will broaden once I have help at Optimo. So I agree with Simon’s suggestions that proportion is critical to a good look. I also think that pulling it off, due to the amount of attention a hat-wearing man generates, requires a level of confidence that is encouraged by the positive feedback from others. At least this has always been my experience and personally, I think that any topcoat or overcoat requires the finished look of a hat. Even as a boy I always thought a grown man looked silly coming in from the snowy cold with an overcoat, scarf, gloves, and nothing on his head -especially if he didn’t have much hair.


Simon, it’s great to see that you were finally able to meet Graham and commission an Optimo hat. The factory (and originally the retail store) is in the somewhat distressed neighborhood where I grew up, and I very much enjoyed visiting the store when it was there, as everyone seemed to share the same passion for making things well instead of quickly or cheaply. It’s fantastic and exciting to see someone pursue their craft with such a passion in my very home town.


I have 4 Optimo hats, two of them have a size tag in them and the other two do not. Yes, I have looked inside the band but nothing???? is this normal for them to be missed?