The Optimo hat factory, Chicago

Friday, November 8th 2019
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Optimo hats in Chicago has to be the prettiest factory I’ve ever been to. 

Over the years I have been to some impressive ones: Hermes, Loro Piana, Zegna. But they’re grand, sweeping, sometimes in sculpted countryside. 

Optimo is small and gorgeous. An old fire station that was repurposed by the (famous in Chicago) architects Skidmore Owings & Merrill, it has polished floorboards and brass fittings.

The floors are scrupulously clean - partly because all the power and air is pumped up from the basement. 

The machinery is all old - anywhere from a decade to a century - but it’s clean. And upstairs is an entertainment area with Graham’s jazz record collection, massive speakers, and shelves of vintage hat-making equipment. 

It’s actually very similar to an old Northampton shoe factory, like John Lobb.

There are wooden floors, old iron machinery screwed to the floors, product being carefully fed into one machine or another, and then set to rest on trolleys. 

The difference is the efficiency and the cleanliness. Even those trolleys are beautiful, and specially commissioned.

I think it's how a shoemaker might dream his factory could be like. 

It helps that only five people work here - there’s more space and machinery than production really needs. 

Graham has collected hat-making apparatus consistently for 20 years, and is always on the hunt for a spare model or a different version of something he already has.

None of them are being made anymore, so it future-proofs the company. 

Each machine, inevitably, also has a story. For example, the row of pale-grey machines for blocking panama hats (a completely different process to felts). 

Graham found them in France. He was visiting an old supplier of hat ribbon, hoping to get them to make the vintage quality again, or at least buy up their archives. The owner of the company listened for five minutes and then said ‘you need to talk to my Dad’. 

The father was called, and turned up, and explained at length why it was impossible to make the same quality. Then he asked Graham why he wanted it. Graham explained his mission to make an old, superior quality of hat. The man squinted at him, then said he might like to see the barn. 

Which was rotting and falling down, but (of course) full of old panama-blocking machinery. Graham asked if he could buy it. The man laughed. ‘What else would I do with it?’ he said. 

It’s amazing how often I’m told these stories. I think it shows the gap there is between new makers of quality products, and the makers of the equipment that used to supply them. The former still isn't big enough to justify the latter. 

With all the hats, Graham’s drive is always to try processes that were used in the past, to improve the quality (which normally translates as denser, stronger and more consistent). 

So there is the double blocking of the straws, where it is blocked both with forms underneath the brim and crown, and then again later, with forms on top of them (so with the hat upside down). 

Then there is decatisation, which uses steam and pressure and particularly helps the denseness of the felt. 

And there is the ageing of the felt bodies themselves. Beaver felts settle and become stronger over the years you wear them - actually getting better with age.

But if you keep them in the right conditions, they can be like that from day one. You just have to keep track of their age and use different amounts of steam to block accordingly (in the same way you have to with different weights.)

Graham is building a small archive of these old felts in the basement, in what will eventually feel like an old humidor of qualities and colours.

I’ve only visited one hat factory before (Christy’s, article here), but as far as I’m aware there is no other factory in the world with the range of machinery and processes that Optimo has. 

Which is interesting, because most other makers at this level of quality are bespoke, one-man operations. There are a few, but I’ve tried Stephen Temkin (article here), Tamara Williams (the City Milliner), Brent Black (article here) and am trying Cody Wellema. 

Which begs the question, what difference does it make having a factory-made hat at this level, with all its machinery, rather than one from a single person using hand-wielded tools?

The first thing I’d say is that the biggest quality difference is having beaver, rather than hare (like most quality hats) or wool (like most cheap hats). 

Worry about getting beaver first, before the maker. It ages so much better, both in terms of softening and improving over time, and in being stronger - so able to be crushed and reshaped in the hand for example, without being reblocked. 

Then I would say that - on my still limited experience - a bench-made hat like Optimo is a little stronger and denser, and more precise. 

Graham used to make hats by hand too, back when he was taught by Johnny Tyus in his Chicago shop. And he talks about the little imperfections, the slightly different angles, that are inevitable when you’re working with hand tools. 

I notice the difference particularly comparing my Brent Black panama with ones from Optimo. The latter are much sharper (or rather can be - they don’t have to be finished that way). 

Perhaps like hand stitching that looks like hand stitching, some people won’t think this precision so important. But it’s the difference I notice most between the two types of maker. 

Finally, I should say a quick word about the Optimo store, which is easily the best hat shop I’ve been to. 

Partly because of the set up, with lines of hats behind a dark wooden bar, and a special ‘straw room’ with the finest straws exhibited in cases. 

But more importantly, for the manager Tiffani.

I’ve always said that most men don’t realise which hats suit them: that they need a lot of help realising which crowns, brims, colours and even ways of wearing them work. 

No shop I’ve been into really delivers that, from Lock in London to various Borsalinos in Italy. Tiffani did, meticulously, and I’m sure that’s in small part due to the way Graham has trained her, as well as her innate skill. 

It’s just a shame Optimo are only in Chicago. Except that (did you like that segue?) they are in London at the moment, on Savile Row. Graham has just extended their ‘residency’ there, to November 23*. 

It’s 37 Savile Row (same as where our PS Presents pop-up was).

I recommend going by and having a look, even if you’re not going to buy a hat. Because chances are it will be a while before you get to Chicago. 

Many thanks to Graham, Nina and Edmund for their hospitality while in Chicago. 

*For the sake of transparency, there is no commercial connection here whatever. I just want everyone to know that the Optimo shop is open. Unlike when Optimo were a brand in our pop-up, when they were paying us for the space.

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Darren Thompson

I’ve got a few hats; Optimo are easily the best. Now that I can afford them I won’t buy any more from the others.

I’ve been to the London pop-up inside the Permanent Style Trunk in early spring this year and the Chicago store too; easily the best hat shop I’ve visited. Graham is great – knowledgeable and enthusiastic. Tiffani is honest and has a wonderful manner and eye… there’s something about her. If you’re a hat guy and can afford one (or more) get one (or more)… If not a hat guy, give them a try. maybe they’ll change your mind. Thanks Simon for the article and for your hand in bringing them to London.


This article makes me REALLY want one!

Andy Poupart

I completely agree with your characterization of Optimo and I think that the Chicago store is one of the best retail spaces of any type, anywhere. I have felt hats from quite a few makers and Optimo is in a class by itself. I stopped by the Optimo pop-up when I was in London recently and I thought they managed to capture just a hint of the flavor of the Chicago store, which is quite an achievement. I recommend Optimo to anyone who wants to buy a hat. Graham and his team make the best felt hats money can buy.


A piece of constructive criticism on Optimo (and some menswear stores more generally), because I imagine someone from there might read this. Perhaps what follows is no longer true. Perhaps they have improved since I visited. I hope they have.

A few years ago, I lived in Chicago for a bit and went to Optimo (immediately after going to Leffot–a very nice experience with superb customer service). I told them I was interested in their hats and had heard good things about them, but that I had no experience with the sort of hat they sell. They said “ok” and basically ignored me, and the person I was with, after that (ordinarily something I wouldn’t mind, but all the hats at Optimo are behind a counter, so you can’t really browse on your own). They had no other customers there. So, not being able to see their hats, I saw they had another room, I was wandering back there, when they pretty sternly told me I wasn’t allowed to go back there. Fine. So then I left, empty handed. Maybe I would have gotten something had they not been so curt. The person I was with wore hats on occasion and he might have gotten something also. Even if not then, maybe down the line.

I am not really sure why menswear stores are so snooty sometimes. It hurts their business and offends the customer. A hat is no more expensive than a good laptop or good jewelry and far less than a car, but businesses that sell those sorts of things are rarely so snooty in my experience. Perhaps more people don’t buy nice menswear because the experience can be such a turn-off at some places.

A few points of clarification:

1. This was not a case of racism. I often hear stories like mine from black people.
2. Not that it should matter, but I wasn’t wearing tailoring. I was probably wearing nice casual clothing, e.g. OCBD, chinos, Aldens. Regardless, what the customer is wearing shouldn’t matter.
3. This was a few years ago (2 I believe), so things might have changed.
4. Normally, I might give the salesperson the benefit of the doubt–maybe they were having a bad day. But there were 2 salespeople and no other customers in the shop.

Maybe there would be more hat shops remaining if hat shops didn’t treat their potential customers like this. The quality of service was especially bad in light of the customer service I had just received at Leffot where the guy who runs the Chicago location (Sean, I think) talked with me and the guy I was with very exuberantly for over an hour.


No clue. Haven’t been to other serious hat shops (don’t know of any others in the US). It was definitely a generalization on my part. I have seen aloof salespeople at other menswear stores on occasion, although never this aloof. I think this attitude turns a lot of people off towards menswear, especially when proper menswear can be intimidating enough to the uninitiated. Traditional menswear can hardly afford this as it is already unpopular enough.

I think that hat shops need to make an extra effort not to be aloof as hats aren’t terribly popular. They won’t get more people interested in hats by being distant. Again, my experience was only the experience of one person (actually two) one time. I wish I had a different experience because their hats do look nice.

I am probably younger than most of their customers. This might have had an effect. But all the more so, stores of a dying breed like this should make an extra effort to reach out to younger customers.

One extra thing: I feel like some salespeople feel like they need to be reserved because menswear is supposed to be “serious” or something. I am not sure that anyone appreciates that attitude, though.

Peter O

Dear Simon,
EL in his reply first now refers to his age and dress when he visited Optimo. What he writes about Optimo salepersons makes no sense. Both shop and factory are in quite down-to-earth locations in Chicago and their reaction wasn’t because they are “snooty”. He isn’t conscious how he appears and he admitted he’s not from Chicago – I suspect he’s the one who puts on airs
felt to be fake in the Windy City.


Interesting. To me, it feels like it boils down to personal preference.
To give an idea about this, when I enter a luxury store, there’s usually someone who asks if he/she can help me. Most of the time, my answer is that I’m just browsing.
I like having a general look in the shop. Do I like what I see in general? How is the atmosphere here? Is it within my budget? Is there something that I’m specifically attracted to? I like covering those points by myself, without a salesperson constantly trying to make out what I’m looking at and commenting on it, endlessly telling me to try this or that, and we also have that colour, etc. I remember a store where the salesperson, seeing I was interested in trousers, wanted me to try on every single model of their current collection. Even after I clearely stated that I didn’t want corduroy, the answer was “but ours isn’t the same”. Or the salesperson at Cifonelli’s shop in London, to whom I expressed I was only here to have a quick look to see the shop for the first time, but don’t have the time to try on anything today, who still offers me to try every single item I looked at, wanting to measure me, bref, pressurising into buying. There’s nothing that’ll do more to convince me not to buy that such behaviour. If I need help, have a question or want more information on something, I can find a vendor and ask. And if I’m on time pressure and want something more or less specific (a new seater maybe), I then answer “yes, this or that is what I’m looking for”.

I guess it’s not easy to attend to both customers who want to be looked after at every turn and customers like myself, who prefer to, in a way, assess the shop by themselves before making a decision.

Nina Thompson

What a disappointing review.

Hi E L – my name is Nina Thompson, from Optimo.

We don’t often get bad reviews , so I take them seriously, and use them to improve our business, so thank you for taking the time to post this.

My email is [email protected] – please email me so that I can find a way to raise your estimation of us.

We pride ourselves on customer service, and our team gets trained extensively on this.

We have a racially diverse company that services a racially diverse client base – and have zero tolerance when it comes to perceived discrimination from both sides.

Unfortunately, because it was two years ago, there’s not much I can do.. other than reminding my current staff about treating everyone who walks through the door with the same respect and attention to detail that we are known for.

Please accept my sincere apologies- I hope you drop me an email.




Great article Simon! I stopped by the pop-up in London recently and absolutely loved the products! I have always loved hats and currently have a Lock panama and Muehlbauer felt. I find the panama works well as I usually wear it with a t-shirt and shorts by the beach. The felt has a bit of a modern kick to it (no band, narrow brim and slightly asymmetrical). Yet I am too much of a coward to wear hats in London, so they end up being worn on holiday or in the country. I am not old enough to not give a damn and just do whatever I want and I don’t have long hair to pull of the rocknroll look. So I was wondering, perhaps you could do a post on the sort of outfits (yours or people you know) work well with hats? I’m thinking felt with leather jacket or parka, would give a bit of balance and make the look a bit more 2019?

Robert Giaimo

I’ve been buying hats for over 25 years, and recently bought my first Optimo hat–there’s really no comparison. I spent some time on the phone with Tiffani figuring out the style and material and I couldn’t be more pleased. I still hope to make it to their store, as someone who appreciates the esthetic and quality of vintage things, I think it would be a real joy. Chicago is also a great city for art and architecture if you haven’t had a chance to visit it.

Simon thank you for exposing me to Optimo in the first place, it’s amazing that someone from across the pond found a real gem in my own backyard.


What a fabulous factory and shop.
Clearly a business with a huge heart.


Nice article, but I’d hardly describe the architects of the Burj Khalifa, One World Trade Center, and Chhatrapati Airport as ‘(famous in Chicago)’ – they are among the most famous architects in the world.


I have bought approx. 20 trilby / fedoras hats over the years, mostly from Christy’s, Lock & Co. and Borsalino. However earlier in the year I came across Optimo on one of the PS posts and then went to the London pop-up shop in Feb. 2019. Having met with Graham I placed my order for a Manhattan style fedora in Golden Tan. Spending £1k on a hat was a big gamble (compared to normal hat prices), but it paid off. I was extremely pleased with it!

The quality of the felt is superior to any I have come across previously (from the UK / Italy). The hat is softer to manage than English made hats as its brim can be moulded into shape easily by hand, without steaming and it then stays in place until specifically moved again. But not too soft, as I found with Borsalino hats, which can move out of shape with the slightest bump.

The stitching, lining, ribbon, brim binding and feather were all superbly executed. Also the hat box is as stunning as the hat, a great piece of engineering. Only missing an external label so you can ID which hat is inside.

I love the fact that I now have a unique hat made to my specific head size / shape. In a colour I chose and trimmed with my choice of ribbon / binding etc. I consider the process similar to that of making a MTM suit.

The Optimo team have been great throughout the process. I worked with Graham (owner) on the initial order, Tiffani (shop mgr.) payment processing and Ethan (shipping) when tracking the package from US to UK. They sent me status emails and always replied quickly to any email I sent and also called me when required.

Since Feb. I have purchased 15 Optimo hats in various colours / trim styles, in both their Manhattan and Dearborn models. If I have ever had any problems Graham or his team has always been sorted them out.

I can honestly say I will only ever buy Optimo hats from now on. Expensive yes, but what get is quality. I now have a collection of hats that I expect to last me for decades. Thank you Optimo (and Simon for intro article)!

David Lane

Gary White in Buffalo NY is very much one of those one man operations you spoke of. He is a wonderful craftsman and gentleman. His hats are beautiful and worth seeking out.



Hi Simon, I was in London yesterday for a fitting in Savile Row and was eager to visit Optimo but it was closed.


I visited the London store on Friday too and found it closed. I contacted Graham by email and he told me that their London store has now permanently closed. They might be back in April. It would’ve been helpful if they could put this on the website.


Are there any Italian tailors that visit London who aren’t too expensive?


Yep, who are the Italian tailors who will cost around €3000??

Jai Kharbanda

I spent all of July and August in Chicago, with my only souvenir being a hat from Optimo. I’ve never worn or owned a hat before but their hats are so sublime and so well crafted it’s only a matter of time before I find an occasion.


I loved the Ottimo pop up in London so inevitably ended up ordering a lovely fedora. The quality is superb. What amazes me is how few guys wear hats – they’d rather get soaked in the rain. Yet in the old black and white crowd photos everyone wears a hat. I wonder when and why this most practical of garments fell out of fashion.


for a rollable hat, is beaver always preferred to rabbit? is beaver that much better long term?

Brent Black

Congratulations to Graham and Simon! Beautiful factory and wonderful article.


Based on Simon’s recommendation I visited this gem of a store when I was in Chicago this past weekend and was lucky enough to work with Tiffani. Though my hat wearing is limited to beanies in the winter, Tiffani was ever so patient and gracious in educating my wife and me about different kinds of hats, their uses and portability, detailing and characteristics, and had me try on a few. Wonderful store, host, and experience, without a hint of snobbery or haughtiness. Much appreciated!



I had always heard great things about Optimo but never personally met anyone who was a customer or seen their work. Therefore, thank you for the firsthand report of your experiences. I don’t ever see myself as a customer as I never travel to that part of the country. However, it is still a fine and enjoyable read. Very well done.

If you don’t mind I would enjoy briefly sharing an experience. I have three bespoke hats (all 100% beaver) made by D Bar J in Las Vegas. Two are Western style hats. One “buckaroo” and a “gambler.” I very recently commissioned a fedora which I just received. All three are superb.

David Johnson is genuinely a wonderful guy who does great work. There is also a very interesting backstory story about how he obtained his vintage equipment.

I am not associated with this business and have no financial interest. I’m just a happy customer and thought you and my fellow PS readers would find this interesting. Thanks again.