It took lots of bold steps for Graham Thompson to reach the top of his game and become one of the best fine hatmakers in America. The Optimo Hat Company factory, 1700 West 95th Street, was built from the feisty spirit of a decommissioned 1914 Chicago firehouse.
Visitors walk up a long flight of stairs underneath an eight-foot-tall Paul Natkin photograph of blues great John Lee Hooker wearing an Optimo hat before a 1998 concert at the Arlington Park racecourse. The building’s interior is finished in relaxed materials including blackened steel, walnut and cork. A cool lounge features Thompson’s collection of a thousand jazz LPs. And there are historic items that date back to when Thompson started Optimo twenty-seven years ago.
I’ve known Thompson for twenty-six years. I met him just after he had completed an apprenticeship with the late Johnny Tyus, one of Chicago’s last great hatters. Johnny’s Hat Shop, 79th and Racine, did hats for the Blues Brothers, blues great Willie Dixon and Robert De Niro. When Tyus retired he had no one to take over his business. Thompson stepped up. He saved Chicago history.
In 2011, GQ magazine featured Optimo as one of the seven best hat stores in America, writing, “There are hat stores, and then there’s Optimo, one of the few joints keeping factory-method hat-making alive.” During an interview in his firehouse workshop, Thompson says, “The making of hats like we make hats disappeared from the market. That’s one big reason I make them and don’t just buy them.”
Optimo hats/Photo: Justin Hummerston
Thompson opened his first Optimo Hat Company in 1995 at 102nd and Western. He was twenty-four years old. Optimo is named for a classic straw hat from South America. Thompson loved the magic of the name. In 2018 Optimo moved its factory to the century-old fire station in Beverly. The factory workshop is closed to the public. The hats are sold at Optimo’s shop in the Monadnock Building, 51 West Jackson.
To commemorate the latest Optimo anniversary, the beautiful coffee-table book “The Art of the Hatmaker” was just released in April via Forlaget Ehrhorn Hummerston in Denmark. The 320-page book is a deep dive into Thompson’s career and craft accompanied by stunning portraits of well-known clients such as Jack White, Buddy Guy, Lurrie Bell and chef Johnny Besch. Hooker was his first major musical client.
“I’m a blues fan and when I think of iconic hat wearers, John Lee Hooker is it with his homburg,” Thompson says. “I wanted to do a hat for him so I reached out to his management. They kind of blew me off, like ‘Whatever.’ Then his assistant called back a week later and they said they mentioned it to John. He said he was a 7 1/2.”
The connection was made in 1997 when Thompson was still relatively new to the game. Thompson sent the hat to Hooker’s home in Vallejo, California, outside of Oakland. A couple of weeks later he was cleaning hats in the back of his store. Thompson’s girlfriend told him he had a call from California. “I pick up the phone and it’s Hooker,” Thompson says with an everlasting smile. “He’s stuttering a little bit and says, ‘This is beautiful. Thank you.’ I had seen pictures of him. I knew what he liked. And I nailed it. And if you look closely at that Natkin picture he put pins and shit in his hat. Then he wanted a blue one, a brown one. I made hats for him until he died. We were the only ones making hats for him. How can you get cooler than that?” Optimo made hats for Hooker until he died in 2001.
“About the same time I started with Hooker I went to Buddy Guy in his club and said, ‘I’d like to make a hat for you.’ He said, ‘I never wear hats.’ I said, ‘Well, you did in 1974 or whatever.’ I was all geeked out on album covers.” Guy’s late harmonica-playing partner Junior Wells was known for his natty fedora. Tyus worked on hats for Wells.
Thompson is not shy. He is very confident. Thompson told Guy that if he ever changed his mind to give him a call. The sudden change of heart for Guy was the realization that Thompson made Hooker’s hat. Thompson recalls, “ He turned around and goes, ‘You’re the guy! Sit down. I was asking John where he got his hats and he wouldn’t tell me.’ He didn’t want Buddy to copy his style. And John knew I was in Chicago. They were messing with each other.”
Optimo has since made at least twenty hats for Buddy Guy. One of the earliest hats Thompson made for Guy was a homburg. Thompson told Guy about an extra-thin beaver material Thompson had developed for him in Italy. It was elegant and thin, yet it can be rolled up. It was soft and easy to travel with. “That’s what Junior used to do with his hats,” Guy told me in 1999. “He used to roll them up and put them in his pocket.” Guy and Thompson settled on an old-fashioned brown homburg with one-hundred-percent beaver fur felt. The hat’s high crown gave Guy the regal aura of a 1950s bluesman.
Guy was electric style. And Thompson likes to say that the hat is the seat of style.
Optimo’s shop in the Monadnock Building, 51 West Jackson/Photo: Justin Hummerston
“For me, a hat is the most personal and iconic thing,” Thompson says. “When I’d watch old film noirs with my Dad, it was the hats that my eye went to. When I see a picture of Bob Dylan, Hendrix, all the way back to Bogart, how could they not have a hat on? Think about the cowboys without their hats. The dignity of dress. I don’t like to use the word ‘crown’ and there’s something to that, but it is this utilitarian luxury item. That’s why it’s style. It’s also a thing that most absorbs and reflects a person’s lifestyle. A hat is not everyone’s thing. For some people, it’s the car they drive. It’s your glasses. And when I see hats, unless it’s really old, they’re all bullshit hats. You don’t know how to put it on. Most people don’t know that.”
Optimo has made hats for Sean Penn, Woody Harrelson, Chris Rock, the late Bo Diddley, Louis Farrakhan and Bill Murray, among others. Years ago Murray’s friend Andy Garcia was directing a film and sent Murray to Optimo. “Bill got some hats from us for films and I’ve seen pictures of him wearing them off-camera,” Thompson says. “It was fun to chat with Bill Murray for a little while.”
In “The Art of the Hatmaker,” Eddie Vedder wears a short-brim Western hat that pays tribute to the early 1900s Hawaiian cowboy. He writes, “My appreciation for cool-looking hats goes back to the summer of 1978 and seeing ‘The Last Waltz’ in a pot-smoke-filled theater in Chicago. The way that Bob Dylan, Neil Young and the Band wore them, It was a look unattainable for a thirteen-year-old, but the impression was indelible… Years later, when I was able to purchase a truly fine example (a brand new one), I could feel the vision, artistry and tradition that went into it. Had to smile when I discovered it was made in Sweet Home Chicago.”
Optimo hats range in price from $795 to $20,000 for those made with the finest custom museum straw. The average price is $1,500. Thompson and his team design most hats by listening to the client before looking at the client.
“We talk,” he says. “They’re designing their own hats a lot of times. I just try to get an idea of the vibe. There are some general rules. Part of it is the face and build. Like if you’ve got a big build and a big face you normally don’t want a tiny brim. But you can break the rules. Similarly, if you’re small and skinny you don’t want a huge brim. Sometimes if you only get a hat extremely tailored for the face or the body then you look kind of plain. We try to mix those things up. I look for cues. Does someone have a bit of a Western vibe? Maybe I spot that they’re wearing boots.”
Thompson takes off his brown gouster and explains, “This is the forgotten hat. A real hat. It’s taken me all this time to get comfortable enough to wear a gouster. Everything else I wear is smaller and a bit more conservative. My hair is a little long now so I can wear a little more brim because it balances it. The wearer itself has to know how to wear it. If you look at John Lee Hooker, the unsaid thing is that would you ever have gone up to him to say, ‘Let me see your hat!’ You know it’s something special and that’s how our customers feel. We’ve had customers punched over people grabbing hats.”
Earnest Miller at Jazz Showcase/Photo: Justin Hummerston
Great Chicago rivalries include White Sox-Cubs, ketchup-mustard, and the gouster-Ivy League style of hat.
The gouster wide-brimmed hats were inspired by Italian mobsters. “The Art of the Hatmaker” features a 1940s-era photograph from the historic Gerri’s Palm Tavern, 446 East 47th, with all the men wearing gousters. The Ivy Leaguers deployed a preppy dress with more cool confidence. Jazz giants Miles Davis and Thelonious Monk wore Ivy League-inspired hats. Later this year Optimo is rolling out “The Monk” in its iconic series collection.
Beloved Chicago hat wearers Phil Cotton and Earnest Miller have been friends for twenty-five years. Cotton, seventy-three, leans into the Ivy League side while Miller, seventy-six, is more gouster. They are included in “The Art of the Hatmaker.” They have a muscular yet playful chemistry that is pure Chicago.
Their hats do not collect dust.
During a conversation at the firehouse I inquired if there was any kind of rivalry between them. “No, we don’t have a rivalry,” Cotton declares. Miller replies, “No.” Cotton smiles, then adds, “Not necessarily.”
Miller was born and raised in Chicago. He had been to the Optimo on Western Avenue, but only met Thompson during a 2019 tour of historic Chicago blues sites that was led by former City of Chicago historian Tim Samuelson. Thompson was driving the van. Beverly blues fan Dorothy Slaughter invited Miller to the event.
“Her husband is John Slaughter,” Miller says. “John is still hardcore gouster. He lived it. He comes to my house on Sundays to watch the Bears. He goes to the Grand Ballroom at 63rd and Cottage Grove. They still have the steppers set. I don’t attend anymore. The majority of the older steppers wear gousters. If you ever want to see the gousters that are living and breathing now, follow the stepper’s set.
“The gousters were harder than the Ivy League, some were in the gang element. During the 1960s and seventies you had to be careful. There weren’t the killings and shootings like now, but you could get your ass handed to you. If a girl invites you to a party and you don’t know anybody at that party and everybody is sizing you up—you know what I’m saying? It can go left. I wasn’t the only one unique, but I had the South Side background and the West Side. To be honest with you, the guys on the West Side were tougher than the guys on the South Side.”
Miller has lived on the South Side, the West Side and the North Side so he understands how territorial Chicago can be. But his congenial personality and classy look enabled him to float between parties in all kinds of neighborhoods.
Phil Cotton and Earnest Miller at Jazz Showcase/Photo: Justin Hummerston
Miller and Cotton bounce back and forth throwing out names of long-gone Chicago clubs: Robert’s Show Club, High Chaparral, Perv’s Place (run by the late Pervis Staples of the Staple Singers), Tiger Lounge, the Twilight Zone. Miller stops and says, “Now this is where Ivy would be in trouble. The Green Bunny, 70th and Halsted. Everybody in there was all gousted up. And they were GD (Gangster Disciples). You had GD and P-Stone Nation on the South Side and Vice Lord and Cobra gangs on the West Side. I was a close friend of a chick named Alice. For reference, Alice always had an ice pick in her purse. She was going with one of the guys from P-Stone Nation and that’s how I ended up at the Green Bunny.”
Cotton and Miller now live quietly in Beverly. Cotton says, “I only went to a few gouster parties, but at an Ivy party I’d wear my Brooks Brothers hats, double-breasted suits and skinny pants like I got on today. Ivy Leaguers were keeping our style under wraps so nobody knew our business, unless you wanted them to know your business.”
He looks at Miller, laughs and adds, “And dare I say we got just as many girls as you guys.”
On this Saturday afternoon Cotton is wearing a beautiful Optimo long-hair beaver in black diamond with a short brim. The smooth Ivy League-style is accented by a vintage ribbon. “It seems to be a part of me,” he says.
Cotton is originally from Buffalo, New York. His father, Curtis Cotton, was a bartender at the esteemed Pine Grill and historic Statler Hilton Hotel in Buffalo. “I grew up listening to (B-3 organist) Jimmy Smith, B.B. King, I’m pretty sure Buddy Guy came through on occasion,” he says. “As a kid I couldn’t drink, so they gave me a ‘Grenadine Milk.’ I’d sit at the bar. I had two brothers who were bartenders. At the Pine Grill you would be dressed up with a nice hat, suit and tie. It was more Italian style. More clean. The pimps dressed in a more extravagant way. But even some of them were clean, like businessmen. They didn’t want to be too showy. We were smooth. The hats were always classic brimmed hats. The musicians always wore ties and suits. Miles Davis, Dexter Gordon, those guys were straight-ahead Stetsons and Italian shoes. There was a sense of quiet about your coolness. The blues guys were a little more flamboyant. I picked up on all that growing up. I didn’t discover the gouster style until I came to Chicago.”
In the fall of 1972 Cotton landed in Chicago to attend graduate school in visual design at the Illinois Institute of Technology. He didn’t know anybody in Chicago. “I was living in Hyde Park,” he says. “What’s the best way to meet people? Give a party. I started giving parties in my studio apartment, massive numbers of people, music, food and all that. It was a tear,” and he nudges Miller.
Miller fist-bumps him. They both laugh. They are two very cool cats in their hats. “We’ve known each other a long time,” Cotton says. “We’ve been down a lot of alleyways. The whole fashion thing and music was intertwined in my DNA from the beginning.”
It is the same deal with Miller. He remembers saving loose change as a teenager so he could buy hats. “Prior to when Dr. King got killed, West Roosevelt Road and West Madison were meccas for shopping,” Miller says. “I remember looking in the windows and seeing all these wonderful hats and saying, ‘One day I’m going to be able to purchase those.’ When I got to high school (Harrison in South Lawndale), we didn’t go to high school looking like these kids do now, bum-ass stuff. I wore sportcoats. Even back then I wore beaver hats.”
At this moment in time Miller is wearing a dark green old-school Optimo fedora. “My hat is a 47th Street hat which a lot of guys wore in the late 1950s and sixties,” he says with a note of pride. “I wear the hat up but I can also do this,” and he lifts a hand to dip the brim. “So I can give you another flavor just by changing the bill on it. This is as individual as the hair on your head. When you come out in your hat you are making a statement. I grew up watching my uncles, my Dad, all the guys in the neighborhood with their hats. These guys would wear the Knox hats. The Borsalinos. The Stetsons. I couldn’t wait to be a grown man to wear one. As a kid going to church I wore a pork pie hat. I had the full suit on, top coat and tie.”
Phil Cotton and Earnest Miller at Jazz Showcase/Photo: Justin Hummerston
At last count Cotton says he has twenty-seven nieces and nephews. “Our nephews look up to us and the way we dress,” he says. “They start emulating that. They were in their late thirties or forties when they got into that. They thought it was cool, a way of being respectful to their elders as well as bringing back that style.”
Miller adds, “I’m kicking up on eighty. I’m respected by my family, ‘Uncle Ernie is a cool dude, he dresses cool.’ Auntie Eloise, my wife, she dresses cool. I do question the younger generation. They’ve been so hip-hop, pants off their ass, all that for so long, so when it comes time to clean up, what are you going to do?”
Thompson is accustomed to hearing questions about the future of his craft. He reflects, “There’s always a desire for the old-school stuff; the styles, the cars, old movies. Around their thirties they start dabbling in it. Occasionally we get twenty-year-olds. They’ve been thinking about it, but they’re not really comfortable until they are in their forties.”
Now comfortably retired, Cotton was an art and design teacher at assorted Chicago public schools. “There is a saying in design that design is circular. Good design comes back,” he says. “Hats are a matter of respect. One of the things people used to ask Richard Pryor was, ‘Why are you always holding your thing?’ He would say, ‘Well, you’re taking everything else from us.’ The pride in clothing and wearing hats is a way for Blacks to have a sense of empowerment. We dress well, we feel well. We may not have the wealth the rest of society had but as an individual, we’re coming out with the right hat, the right suit and my lady’s looking good. That’s important. A hat is a part of me that is me! Nobody else. That’s what I get out of the whole idea of fashion and civilization. You take it from who is in control and who is the slave. Because there are slave mentalities still going on in society—unfortunately.”
Cotton met Miller when they worked together at the National Teachers Academy in the mid-2000s. Cotton was teaching art education and design. Miller was designing tech infrastructure for the Academy. In the 1980s Miller produced radio and TV at Chicago Access and in the early 1990s he produced “In Focus With Chicago Public Schools.” During the 1970s Miller was also a freelance photographer for Chicago newspapers.
Cotton first encountered Thompson at the Optimo store on Western Avenue. He had purchased a half-dozen hats that had belonged to a Black neurosurgeon at an estate sale in the Pill Hill neighborhood of Chicago. “But these hats were filled with smoke,” he says with a smile. “This guy was an incredible chain smoker. He was a brain doctor. And a smoker. I brought a few of them to Graham to clean those hats.”
In 1980 the hat connoisseur founded Phil Cotton Design, a commercial, advertising and product design business in Chicago. His clients included North Michigan Avenue ad agencies and social service companies such as the Red Cross. Cotton has an eye for detail. He looks straight ahead at a cabinet filled with some of Optimo’s most treasured hat tools and says, “It is fascinating to see these beautiful old machines and the things they would do to make a hat that you never think about. It’s technology, but hands-on technology. I love the hats but I also love the process Graham goes through.”
Roan leather sweatbands are gently installed/Photo: Justin Hummerston
The Optimo Hat Company has fashioned an evocative workshop. Hats are made on the first floor of the 7,700-square-feet former firehouse. The ground level contains three distinct, dimly lit rooms: one for production, one for sewing and one for surface finishing. Custom-made shelving is used for storing hat forms and molds. Thompson keeps a homage to his past on the second floor. A porthole window flush with the second-floor steps commemorates where the original fire pole was and allows for a view of the production operation below.
A second-floor display case features the original Johnny Tyus tools and equipment on which Thompson learned his craft. “There’s a lot of sentiment there,” Thompson says. “Like his irons, His hands were on those all the time. You can see how they have worn down from years and years. I got trained on all of this.” Racks in the second-floor loft space include hats that Optimo is recreating from the 1920s, thirties and forties.
“Most everything upstairs is retired,” he explains. “Downstairs we use everything.” The ground level contains functioning straw-blocking machines from the early 1900s through surface-finishing machinery from the 1950s. The space is a working museum.
“Every machine has a story,” Thompson says. “There’s cracks and gouges in them but it is super-efficient to make hats in here. I spend a lot of time in the surface-finishing room. It’s where we do the sanding, polishing and pouncing. My hatter’s bench is in the room. That’s where I do creasing and polishing. I do a lot of the same things I did on Western back here. It’s been a labor of love restoring this. We had to replaster the whole place. This was exactly the right amount of space and layout for when I wanted to expand. It was perfect. We can make more hats out of here.”
Graham Thompson in Optimo’s new workshop/Photo: Justin Hummerston
Was this beautiful workshop his vision or did he take it day-by-day? “For hat businesses this is tiny,” he answers. “But, we make the best hat in the world. That has been my overriding goal. Even when I met you, that was my goal. I met you a year after I opened.”
Thompson, who graduated from Benet Academy in Lisle, met Tyus when he was a sixteen-year-old living in the western suburbs. After high school he obtained a degree in international trade and finance at Chaminade University of Honolulu and a minor in Japanese from Ritsumeikan University in Kyoto, Japan. He returned to Chicago in 1995.
When he came home one of the first things Thompson did was to track down Tyus. The longtime hatmaker told him he was closing his store. “I was saddened by that,” he says. “It occurred to me just as I arrived home. It was in the back of my mind that I wanted to learn a rare craft of my own. My dad was always working on stuff, he’s great with bodywork on cars. He built homes.”
Tim Thompson had worked for General Motors since he was a kid and then started moonlighting and building custom homes, starting in west suburban Westchester. “We were always moving,” Thompson recalls. “We’d have a house, sell it, move. When he was like forty, he quit GM. Threw his pension away and started building more homes (in the Hinsdale area).” Tim Thompson is retired and remains in the western suburbs.
“My dad’s an artist and I kind of caught that where money was secondary,” he says. “That can make you broke quickly. But now we have a cool place. I think it’s gonna all pay off. And it has.”
In November 2013, Graham Thompson purchased the former Engine Co. 121 firehouse for one dollar, according to the City of Chicago Planning and Development. Thompson acquired the property with the requirement that it be rehabilitated. The firehouse had sat vacant for six years and was valued at $190,000 according to city records. The Chicago City Council approved the redevelopment plan, estimating first-floor renovations at $422,000 and second-floor conversion at $400,000.
“The first thing we did with this place was to strip it down to its bones,” Thompson explains. “Then it started to look better because over the years they had partitioned walls and added holes for more firepoles. We took it back to the original designs.”
Thompson initially didn’t have an architect. He was moving in a DIY cadence, slowly cleaning up and stabilizing the building. He fixed some leaks. He looked for some exterior sun. He decided to reach out to a retired partner from Skidmore, Owings & Merrill (SOM), known for the original Sears Tower, NATO headquarters in Belgium and the Seven World Trade Center in Manhattan.
“Something was wrong,” Thompson says. “I couldn’t move my stuff in here. I needed to talk to someone about getting some design in here. Especially on a workflow. I thought there was no way SOM would take this. It was too small. I didn’t have the budget. But they took the project. It wasn’t exactly pro bono, but it was a neighborhood rate. I was concerned that this was going to be like medical students training on somebody but because there was no money in it and they are a for-profit business, the partners had to work on it. They gave me fairly accurate drawings and then my friends made all this.” And Thompson proudly looks around the beautiful second floor. He continues, “A steelworker pal. A woodworker pal. SOM won awards with this, which was cool.”
The team honored remnants of the building’s former life, including the Chicago Fire Department plaque and marble from original showers which was used in the construction of a new kitchen. In 2018 the project received the American Institute of Architects (AIA) Chicago Design Excellence Award and in 2019 was recognized in the AIA Interior Architecture Awards.
The firehouse project was completed in 2018. “It was the best thing I ever did,” he says. “If you look you can see the order in the architecture and design. This is the smallest factory SOM has done. By far.”
The former fireman captain’s quarters have been transformed into a lounge area filled with vinyl LPs. Thompson’s crew blew a hole in the terra cotta wall to allow southern light to come in. The lounge archway was made of reclaimed pieces from Thompson’s original hat bench. If a visitor looks close before entering the lounge, burn marks from a distant past can be seen. “I sit up here, listen to jazz records, and do my work,” Thompson says. “I bought the vinyl, the corner speakers, and most of the stereo system from a guy that collected music from the late 1940s until the eighties. He lived in the neighborhood. He had passed on and his son sold it to me.”
The latest acquisition for Optimo’s upstairs space is a classic 1955 Hammond B-3 organ that sits in a corner at the top of the steps. The Hammond B-3 debuted in 1955. Optimo’s Hammond formerly belonged to the beloved Chicago keyboardist Marty Sammon, who died on October 15, 2022, one day after his forty-fifth birthday. Sammon played with Buddy Guy and recorded with Devon Allman, Carlos Santana, Kingfish Ingram and others.
Late last year Thompson was having a beer at a bar in Blue Island. His friend introduced him to someone in the bar who played in a local band. “I mentioned I wished I was in a band,” he says. “I said I tinkered around on piano, but I really wanted to learn how to play the Hammond and I was looking to buy one. He said that was so crazy because he had a friend who was good friends with Marty Sammon. And he was selling Marty’s B-3.”
Thompson did not know how to play the Hammond, but he threw his hat in the ring. “It all worked out,” he says. “I got it for a good price but a fair price.” He declines to disclose the sale price but continues, “They didn’t have to pack it and ship it. They said some people were calling from Norway.”
The Optimo factory does not have an elevator. The Hammond B-3 weighs 425 pounds. Thompson, Omar Navar (hat blocker and manufacturer) and the Blue Island guys carried the B-3 up the stairs. “Marty lived just a couple miles from here,” Thompson says. “I didn’t know Marty very well. I’d say hi to him at events. I love it. As soon as you hit a chord with those little bars you get that rock sound. And just listening to (B-3 greats) Jimmy Smith and Jimmy McGriff on vinyl all the time. Sometimes I play my records and then play along. I want it up here because anybody that respects the blues and wants to play it, it’s there. Just come up here and jam. I want this to become a music place where we have little jams up here once in a while. ”
Graham Thompson in Optimo’s new workshop/Photo: Justin Hummerston
Graham Thompson is fifty-one years old. Optimo has a seven-person staff, all younger than Thompson. Does Thompson have plans to mentor someone just as Johnny Tyus mentored him?
“I’m doing it now with everybody who works with me,” he answers. “Lucy (Lucia Tovar de Lozano) is our head trimmer and director of quality control. She has been with us for twenty years. She’s got it. I’m not going to sew anything. Everybody that we have sewing is way better than me. Sewing is all part of hat-making. It used to be very divided: ‘The men are going to make the hats and the women are going to put on the bow.’ Sewing is difficult and intricate more so than a lot of the other processes. I set this up in a way so it would go on and wouldn’t just die with me.”
Tovar de Lozano is Quality Control and Trimming Department Manager. She began at Optimo in 2002. Hat trimming involves installing the sweatband, making the bows, sewing the ribbons onto the hats and finally sewing the linings into the hats. Tovar de Lozano is a patient and thoughtful craftsperson. She wanted to take her time to articulate answers to questions and asked that we correspond through email.
“My mother taught me never to settle for mediocre quality of work whether it was cleaning or drawing,” she writes. “My father set the example of patience. I suppose they go hand-in-hand.” Her mother Lourdes Tovar is a homemaker. Her father Jesus Tovar recently retired after fifty years of working for a manufacturer of packaging and custom printing. The family grew up in the Gage Park neighborhood of Chicago. Before coming to Optimo, Tovar de Lozano worked as a server at the Corner Bakery in the Field Museum. Her best friend was working at Optimo. “The idea of being able to work with my hands and also work in a place that would take me back in time was so appealing to me,” she writes. “I dove into it.”
Brady Leaf is vice president at Optimo. He spends most of his time working with clients at the downtown shop. He has an easygoing but focused personality. The six-foot-five-inch Leaf was quarterback for the University of Oregon between 2003 to 2006. His older brother is former NFL quarterback Ryan Leaf. His father John has spent forty years in the insurance business and his mother Marcia is a retired nurse.
A native of Great Falls, Montana, Leaf has been a fishing guide, has managed bars and has been in sales. He was a trauma rep for orthopedics in Traverse City, Michigan when he contacted Thompson in 2019. “It was taking a risk or a chance,” he says. “I sent Graham an email. I was interested in his brand and I wanted to learn more. I wanted to see about job opportunities, but nothing specific. I was looking to learn the craft from him and work on the business side. About nine months after I sent that email, I got a phone call from him asking if I wanted to come to Chicago and have a beer.
“We both took a leap of faith. I quit my job and moved to Chicago in 2020. He hired me as his apprentice and then as vice president. I’ve been running the shop and he’s been slowly teaching me the crafts. It’s been a great partnership. I was trying to find my passion and it took me a little longer than some people. Every summer we meet up with my grade-school friends in Montana and we go fly fishing. We were sitting around the fire one night talking about how ‘money didn’t matter’ in what you do. I said, ‘I’d like to be a maker of something, like a hatmaker and learn that.”
The next summer the friends reconvened in Montana. One friend reminded Leaf of how he usually follows through on his dreams and how he thought he’d be wearing a hat he crafted. “I had read about Graham’s company,” Leaf says. “When I got home from that trip I got on the internet and that’s when I reached out to him.”
Thompson liked the fact that Leaf didn’t have any prior experience in the world of hat crafting. Leaf says, “His reference was to imagine we were making the best coffee in the world and I had been a barista at a chain. Maybe I learned some bad habits, and then I come to Chicago to make the best hats in the world.” Thompson wanted a blank canvas.
Optimo’s shop in the Monadnock Building, 51 West Jackson/Photo: Justin Hummerston
“Everything I’ve learned has been through him,” Leaf says. “And Lucy has been here so long and has been very helpful. So we’re slowly taking it in stages. Ideally, it would be nice if I could be at the factory every day with Graham and just make hats. On hat-making I’ve been focusing on the felt and me and him have been blocking and surface finishing. Eventually I can be at the factory more and we can hire some more people at the shop. We have a business to run and that’s something I can bring to the table through my experiences of managing small businesses.”
Tovar de Lozano saw the same perfection in Thompson’s principles she witnessed while growing up in Gage Park. “We never settle for a decent bow, for example,” she writes. “We figure how to make it ‘perfect.’ That means using specific needles and threads to make the bow of specific material and tack the ribbons around the hat, using a specific stitching technique to keep the ribbon flush onto the hat, all while keeping in mind how we hold the hat so the brim is undisturbed. So, as we are using our right hand to insert the needle from the inside of the hat and through the ribbon, the left fingers gently hold the bottom edge of the ribbon onto the band line of the hat while trying not to bend the rim.”
Thompson has remained steady over the years. He has not lost his edge. Tyus sold him his hat business in 1994. Tyus made custom hats but he was even more known on the South Side for servicing and renovating precious hats. Tyus allowed the young Thompson to make his payments over time. He also taught Thompson to make hats. And Thompson had to pay the Master Hatter to be a mentor.
“What was good is that you had this intense pressure to get every little thing out of what you were learning because I was paying dearly for it,” Thompson says. “Johnny was a joy to work with and a great mentor. The money coming in back then, we just didn’t make a lot of hats. And when we did make one, I had to pay Johnny to make one. It was like a hot dog stand. There was a local place where I would buy hat bodies (raw material). I’d come back, make it with Johnny, sell it. I was going in the hole deeply. So I kept borrowing. I’ve got almost a delusional positive attitude. Like, ‘That’s okay. If it gets any worse, I’ll just wholesale dry clean hats.’ I remember going over to Franconello’s restaurant across the street to ask them if I could valet park cars at night. They said, ‘No, we’ve got the parking thing down.’ I would work all the time and it was insane. I was taking any credit card, signing up for it, maxing it out, getting cash back to pay for this thing. I barely got through the first year.”
Being a former major college quarterback, Leaf is accustomed to pressure. “We come from a football family,” he says. “I was in a high-stress situation. You have to be able to communicate and lead and that’s what I did in football. And that transfers into all businesses in general, but especially small businesses because you have a small team and you have to be on the same page. I worked for a multibillion-dollar company before this and there are hierarchies to it and you get in line. Here, you have to make adjustments on the fly.”
Entering Optimo’s shop in the Monadnock Building, 51 West Jackson/Photo: Justin Hummerston
When he was a rookie small-business owner, Thompson could not believe he landed a mortgage for his dream. The loan was not co-signed and Thompson said he was working with a “relatively conservative” bank. Thompson promised the bank he would restore the property, just as he later did with the fire station. “The owner of the bank, whom I am so grateful for, gave me the loan,” he says. “I took this property that was an eyesore of Western Avenue, bought it and renovated it.”
About a year later Thompson refinanced his mortgage. He took his refinance money which was roughly $50,000 and paid off the credit cards with $20,000. “And then I took $10,000 and went to Ecuador to get more material. And then I took another $10,000—and everyone is telling me don’t spend a dime—and I found the guy (Blair Hunt) that did the interior design for the first Ralph Lauren store. I knew the place didn’t look right. He lived in Lake Zurich. He comes down in a pickup truck. The first thing he did was, ‘Why do you have all your molds in the back?’ I didn’t know. I just wanted it clean. He said, ‘No, bring all this in.’ So we made the racks and put them out front. And then we put the hats in front of them. I just knew when it looks right, it feels right. And it’s going to be right.”
People started coming in.
“Even the factory colors we have now, walnut, black, Blair brought a lot of that in,” Thompson says. “The Sun-Times hit [a story I wrote about him in 1995] and then I sold a Montecristi hat. I needed this money so badly. I was kind of over the hump.”
“Every time I’ve had a few bucks and if it’s available, I buy tools and equipment. I travel and learn.”
Thompson tapped into the craft movement before it became fashionable. “When I got into this it was weird,” he explains. “It was like, ‘What do you mean you’re making hats?’ The craft movement has become trendy. And trends come and go. You will survive if you are a true craftsman and you apply yourself to doing things right. You can’t be brewing beer and saying, ‘I’m like the guy who has been doing it since 1450.’ Because it takes refinement. Good craft is not crafty. You don’t want to look at something handmade and you can tell.
“Now it is definitely less unusual and there are a lot more hatmakers. With Johnny, I saw right off the bat the hats that were made in the thirties and forties. That was the standard I wanted to hit. We’ve gotten more and more toward that old-school quality.”
Thompson says that in 1914 hat sales peaked per capita in the United States. For example, men were wearing derbies, the collapsible opera hat seen in old movies, and the flat straw boater hat. The industry remained vital through the 1940s. “But hat-wearing was declining,” he says. “That was mainly due to the rise of the automobile. You didn’t need to have a hat. That’s why hats are very much an urban or an island thing. The less time you spend in the sun or the elements, the less that you need to wear a hat.
“In the 1930s per capita was declining but the hat companies were competing on quality. It was elegant, more defined, and beautiful. You also had advancements in engineering and production. You got the best quality hats in the 1930s and forties. During World War II that old style was dating a little bit. American troops are coming back from Europe. It’s not as cold in Europe and they’re not wearing as many hats, it was more caps. No problem. But what changed was the understanding of what real hats are. The industry started to do cheesy advertising. It went from elegant to kind of kitschy and dippy. It probably was a trend, but certainly, there would be several companies that would never do that. You need a lot of equipment, tools, knowledge and material to do this. Small places didn’t have it. Large places converted. It changed what quality meant. And in the sixties and seventies, it just tumbled. By the time I got into the business, there was nowhere where you could get what used to be made. Not one place. That blew my mind.
“People forgot you need a high-quality hat. A guy in a hat company makes a press and they stiffen it up and make a faux version. It was like a clip-on tie. ‘How did you knot your tie like that? I don’t know! Let’s have a tie machine do this.’ You can see how stuff gets bullshit. It’s not weatherproof. Quality starts to dip. Clients don’t know anymore the whole ritual of creasing.”
Thompson neatly creases the brim of his gouster and says, “Al Capone’s hat did not come like this. He put that in himself with his style. And you can do that with a good hat.” Optimo has created “The Capone”-style fedora in undyed white Rex fur, an exotic white rabbit from France. Capone’s go-to place for hats was Maurice L. Rothschild at State and Jackson, just a block away from Optimo’s retail shop.
Optimo’s legacy is resplendently honored in “The Art of the Hatmaker.” The book was a three-year project from the Danish team of Justin Hummerston and Morten Ehrhorn. Thompson had seen their books on cigars and pipes. Hummerston visited Optimo four times. Hummerston and Ehrhorn’s mission was not to promote the sale of hats. Hummerston did the photographs and Claus Lex was the writer.
In the book preface they write, “This book is about passion, respect, craftsmanship and honoring lost traditions. It is an ambition to remind the world—today and tomorrow—so valuable knowledge will not be lost again. This is one of the noteworthy attributes of books. They remember where we forget.”
“They interviewed me for a long time,” Thompson reflects. “So I was researching old journals. I found my notebook from my first year in business. One of my entries was how we should do an elegant coffee-table book on hat-making. Even our best clients and biggest fans don’t know all that goes into hat-making. We wanted to show it’s not just what we do in Chicago, but to explain craftsmen from the weavers to the felters to the block makers. We wanted all of that as well as to commemorate what we’ve been doing.”
Several years ago, Thompson considered opening several Optimo stores around the world. “After COVID, forget it,” he says. “Because doing stores is managing people. I want to work on great hats. So now the vision hasn’t changed that much. I love this place. But we’re doing the same thing we were doing on Western, just always trying to make it better.”
