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Jenny Pfanenstiel

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Would you like to try on a hat? Don’t mind if I do! Pull up a chair, pour yourself some tea and come with me through this journey that I like to call “the making of a milliner.”

Sewing was a hobby that my mother, aunt and grandmother enjoyed — always sewing clothes and toys for both my sister and me. So, when I expressed interest in learning, they were eager to teach. It all started at the age of 5, when they taught me how to cross-stitch. I then moved on to clothes, which was certainly challenging at first. This taught me patience, gratitude and an appreciation for sewn things. I loved being able to create something from nothing, which eventually led me to study fashion design at the Art Institute of Colorado in Denver. After graduating, I moved to Chicago, where I created costumes for Cirque du Soleil, movies and commercials.

I loved making costumes, but I knew something was missing. One night, I attended a lecture where a woman was talking about an age-old technique of blocking hats, where she molded material over old wooden hat forms. Part of what intrigued me about the hat-making process was the old blocks that were used. I loved thinking about the many hands that had once made a hat on that exact block.

I had dabbled in hat making to accompany the costumes I created, but never knew the proper techniques for making them. I found a beautiful cloche hat block from the 1920s at a local thrift store, bought some millinery felt online and started practicing. Just like learning to sew, there were definite struggles. The amount of strength you need to stretch the wet felt to get all the bumps and pleats out was challenging. I remember it took me three hours to block my first hat, restarting the process several times, but I did it.

After drying for two days, I was so excited to take the felt off the block, but when I went to do so, it wouldn’t budge. I didn’t understand what I had done wrong. Eventually, I came to realize that the wet felt fibers had seeped into the wood of the hat block and, when dried, they literally became a part of the wood. I had to rip the felt off the block, destroying the hat. To this day, there are still fibers stuck to the block that are permanently embedded in the wood. I now know that you need to cover a hat block with plastic to protect the wood — and your hat! Though it was heartbreaking at the time, that 1920s hat block now tells the story of how Jenny Pfanenstiel started her journey.

Hat making started out as a hobby in my basement in Chicago to have a break from the corporate world and keep true to my artistic self. Slowly, people started to learn I made hats and I set up my dining room as a showroom and filled it with raw materials, trimmings and hat blocks for people to see when they came over to get a custom hat.

Two years into my hat-making journey, I met a woman from Louisville, Kentucky — home of the Kentucky Derby. I had never been to Kentucky, but she felt my hats would sell well for the big event that takes place on the first Saturday in May. The following year, I made appointments with local boutiques and sold out in one day.

The idea of moving to Louisville and opening my own store became more intense every year, and in 2014 my husband and I packed up to start a new life in Kentucky. I found a small art studio in a converted meatpacking plant amongst other artists. Then, In 2019, I moved to my very own storefront, a cottage that was built in 1877.

I had a vision of creating a whole experience for my clients when they came to see me. I didn’t want to be just another retail store. I wanted to take my guests to a different place mentally and physically, where they are surrounded by old hat blocks, vintage sewing machines, trims, and millinery artifacts.

When a client comes in for a custom hat, we walk through the process of how a hat is made. First, I measure their head. It is important for a hat to fit properly — not too heavy, not too loose, but just right. Then, we try on different styles to find the best shape that works with their physique. We look at the raw materials and trimmings and put together a concept for the finished hat. Each hat can take anywhere from three days to three weeks.

The process starts by molding the millinery material over the hat blocks by wetting and steaming it to create the shape of the specific block. Once all the pleats and bumps are removed through the blocking process, it is tacked and roped down. When dry, which can take one to three days, I remove the material from the crown and brim blocks, cut away the excess material and hand sew the crown and brim together. A sweatband and wire are added for additional comfort and stability. Finally, we add the embellishments, whether that be a feather flower, sculpted horsehair bow, or handmade flower. I allow my imagination to soar with no boundaries to create the perfect custom accoutrement — hats not only complete your style, they create a wearable journal of life’s adventures.

From Formé to the next venture

Let’s talk about hat boxes — something that is valuable in the hat world. When I started making hats in 2007, it was import- ant to me to present my work in a way that alluded to quality and craftsmanship. I found a great company out of Canada that had been making hat boxes for 100 years. There were some things I would change about the boxes, but they were better than the alternative square, flimsy boxes that never fit a hat and were made more for gifting a shirt.

However, in 2016, my hat box supplier closed its doors with no one to take over their manufacturing. I was at a loss and determined to find a solution. I located a packaging company in New Jersey that partnered with a local paper mill that produced recycled products. I worked with them to create a template for the perfect hat box. I needed it to be collapsible because I didn’t have a lot of room to store the boxes. I wanted it to be a unique shape to stand out and, so, we went with hexagonal. Then I thought: Why not create three hat box sizes to fit three of the most popular hat styles I sell?

All my hat boxes were made with the Formé Millinery logo, and I felt it really added an additional element to my brand. They were sturdy, made of recycled materials, and made in the USA. People bought them whether they bought a hat from me or not. This got my husband, Bart, thinking: If you were having a problem getting hat boxes, then surely other people or companies are, too. Why don’t we start a hat box company?

And in 2017, Hat Boxes USA was born to fill a void in the market. We understood the challenges associated with finding quality hat boxes to accommodate the large array of hat sizes and styles — and we knew the importance of protecting these heirlooms. Bart took on this challenge and started the business in the basement of our home. Boy, do hat boxes take up a lot of room!

We decided to put them for sale on Amazon. Initially, we were just hoping to cover the Amazon fees. In the first month, we were able to pay our fees and then some. We were selling hat boxes faster than we could have them produced. Wayfair then reached out to us and wanted to sell our boxes under their name. Just as Bart predicted, not only did hat makers like me need hat boxes, but also boutiques, hotels, movie sets and travel agencies — even cruise ships ordered hat boxes from us by the hundreds.

Things were going well and we were beginning to make a name for ourselves within the hat community. Then, Judith Mishler, who owned Judith M Millinery Supply House in La Grange, Indiana, contacted us. I knew Judith because she had one of three millinery supply houses left in the U.S. I bought many raw hat-making materials from her over the years, and taught hat-making workshops at her place, which was located in the middle of Amish country a couple hours outside of Chicago.

With the pandemic in full swing, Judith was looking to retire after almost 30 years in business. She knew Bart and I were heavily involved in the hat world and asked if we would be interested in taking over. We certainly didn’t want to see her close, like so many other hat companies had done over the last 10 years. So, we thought: Well, we are in the middle of a pandemic … it is probably difficult to get a loan right now … we don’t know when all of this will turn around … yes, let’s go for it!

People thought we were nuts. So did we, frankly, but we were going to see if we could make this work. The signs were already pointing in our favor because we lived in La Grange, Kentucky. So, we packed up Judith M in La Grange, Indiana, and moved the business to our La Grange.

Hat Boxes USA was doing well, and we really needed to move it out of our house, so we decided to open a storefront in our little historic town for the new headquarters for Hat Boxes USA and Judith M Millinery Supply House. We kept the original name of Judith’s business, her website, and even phone numbers. She had created such a name for herself in the industry and we wanted to continue her legacy.

Bart now runs our La Grange store. We sell all the raw supplies to make a hat from scratch — any material you can find from across the globe. We sell to the millinery and costume departments of Disney, Warner Bros., opera houses, universities, etc. The store is open to the public, so we also get hat makers who come visit us to see the supplies in person.

Just when we thought we had created our own little happy hat family and everything was going well, a big uproar occurred in July 2023 in Louisville. A local craft store that had been in business for 52 years was closing. It specialized not only in home goods, but also had a big business during the Kentucky Derby when they decorated hats for people.

When I say big business, I mean BIG. I mean: They sold roughly 4,000 hats from March to May. Now, their hat business was very different from Formé Millinery, where I create hats from scratch, and from Judith M, which sells raw materials. This craft store sold hats that were already made, but not decorated. They sold every hat base shape you could think of, and feathers, flowers, ribbons, etc. People would come in, pick out a hat base, and then select all their embellishments and either glue it together themselves or have the shop’s designers do it for them. The shop turned completed hats around in a day.

With the store’s imminent closure, people literally went into a panic. The hats there were sold at a particular price point that was less than a truly custom hat and appealed to a large market. Bart and I thought we needed to do something. If someone was going to step into this market and save the “hat” day, we were the best pair to do so. We had already established relationships with the manufacturers who make the raw materials so we could just work with them in a dif- ferent way and have them make hat bases for us, too.

During this time, we knew we would need a storefront that would have a lot of foot traffic like the craft store did. We even considered moving into the old store, but it was in much need of repair.

We found a wonderful place within the same area in an outdoor mall that also had JOANN, Trader Joe’s and World Market. This was a perfect place and great size (our biggest store), but very expensive. The landlord was not willing to do a pop-up shop, only a three-year lease — at the minimum.

To make this work properly, we needed to be open by the end of the year to work out all the kinks before the Derby rush. This was certainly going to be the biggest (and most expensive) business decision Bart and I had ever made. We decided to bite the bullet and take the plunge: We opened our third store, The Hat Shoppe, on November 10, 2023.

It’s a full-service hat shop with, of course, Derby hat-making supplies and hat bases ready-made for decorating, along with feathers, flowers and ribbons, plus we have a men’s hat lounge and a hat bar where you can make and brand your own felt hats. We also conduct hat-making workshops of all types and bring in guest instructors. We still feel very new, and this store does operate differently than Formé and Judith M, so we are still working out all the kinks (of which there have been many). With a three-year lease in our future, success is our only option.

It has now been 17 years since I started making hats in my basement in Chicago. I am a five-time Featured Milliner of the Kentucky Derby. I make ongoing hat collections for Vineyard Vines, J. Peterman, Keeneland, and Brown-Forman, to name a few. I am also a hat designer for McCall Patterns and the author of the book The Making of a Milliner. My hat clients include Oprah Winfrey, Madonna and Barbara Cochran.

At the end of the day, Bart and I come home to more gray hairs. Amelia is 8 years old and has grown up in the world of hats and entrepreneurship. She has her own little corner in every shop that is her happy place — when she is not playing with the feathers or helping customers. If you are in the Louisville area, come see us. Try a hat on, buy a hat, or experience one of our hat workshops.

Regardless, always make it a hat day.

Would you like to try on a hat? Don’t mind if I do! Pull up a chair, pour yourself some tea and come with me through this journey that I like to call “the making of a milliner.”

Sewing was a hobby that my mother, aunt and grandmother enjoyed — always sewing clothes and toys for both my sister and me. So, when I expressed interest in learning, they were eager to teach. It all started at the age of 5, when they taught me how to cross-stitch. I then moved on to clothes, which was certainly challenging at first. This taught me patience, gratitude and an appreciation for sewn things. I loved being able to create something from nothing, which eventually led me to study fashion design at the Art Institute of Colorado in Denver. After graduating, I moved to Chicago, where I created costumes for Cirque du Soleil, movies and commercials.

I loved making costumes, but I knew something was missing. One night, I attended a lecture where a woman was talking about an age-old technique of blocking hats, where she molded material over old wooden hat forms. Part of what intrigued me about the hat-making process was the old blocks that were used. I loved thinking about the many hands that had once made a hat on that exact block.

I had dabbled in hat making to accompany the costumes I created, but never knew the proper techniques for making them. I found a beautiful cloche hat block from the 1920s at a local thrift store, bought some millinery felt online and started practicing. Just like learning to sew, there were definite struggles. The amount of strength you need to stretch the wet felt to get all the bumps and pleats out was challenging. I remember it took me three hours to block my first hat, restarting the process several times, but I did it.

After drying for two days, I was so excited to take the felt off the block, but when I went to do so, it wouldn’t budge. I didn’t understand what I had done wrong. Eventually, I came to realize that the wet felt fibers had seeped into the wood of the hat block and, when dried, they literally became a part of the wood. I had to rip the felt off the block, destroying the hat. To this day, there are still fibers stuck to the block that are permanently embedded in the wood. I now know that you need to cover a hat block with plastic to protect the wood — and your hat! Though it was heartbreaking at the time, that 1920s hat block now tells the story of how Jenny Pfanenstiel started her journey.

Hat making started out as a hobby in my basement in Chicago to have a break from the corporate world and keep true to my artistic self. Slowly, people started to learn I made hats and I set up my dining room as a showroom and filled it with raw materials, trimmings and hat blocks for people to see when they came over to get a custom hat.

Two years into my hat-making journey, I met a woman from Louisville, Kentucky — home of the Kentucky Derby. I had never been to Kentucky, but she felt my hats would sell well for the big event that takes place on the first Saturday in May. The following year, I made appointments with local boutiques and sold out in one day.

The idea of moving to Louisville and opening my own store became more intense every year, and in 2014 my husband and I packed up to start a new life in Kentucky. I found a small art studio in a converted meatpacking plant amongst other artists. Then, In 2019, I moved to my very own storefront, a cottage that was built in 1877.

I had a vision of creating a whole experience for my clients when they came to see me. I didn’t want to be just another retail store. I wanted to take my guests to a different place mentally and physically, where they are surrounded by old hat blocks, vintage sewing machines, trims, and millinery artifacts.

When a client comes in for a custom hat, we walk through the process of how a hat is made. First, I measure their head. It is important for a hat to fit properly — not too heavy, not too loose, but just right. Then, we try on different styles to find the best shape that works with their physique. We look at the raw materials and trimmings and put together a concept for the finished hat. Each hat can take anywhere from three days to three weeks.

The process starts by molding the millinery material over the hat blocks by wetting and steaming it to create the shape of the specific block. Once all the pleats and bumps are removed through the blocking process, it is tacked and roped down. When dry, which can take one to three days, I remove the material from the crown and brim blocks, cut away the excess material and hand sew the crown and brim together. A sweatband and wire are added for additional comfort and stability. Finally, we add the embellishments, whether that be a feather flower, sculpted horsehair bow, or handmade flower. I allow my imagination to soar with no boundaries to create the perfect custom accoutrement — hats not only complete your style, they create a wearable journal of life’s adventures.

From Formé to the next venture

Let’s talk about hat boxes — something that is valuable in the hat world. When I started making hats in 2007, it was import- ant to me to present my work in a way that alluded to quality and craftsmanship. I found a great company out of Canada that had been making hat boxes for 100 years. There were some things I would change about the boxes, but they were better than the alternative square, flimsy boxes that never fit a hat and were made more for gifting a shirt.

However, in 2016, my hat box supplier closed its doors with no one to take over their manufacturing. I was at a loss and determined to find a solution. I located a packaging company in New Jersey that partnered with a local paper mill that produced recycled products. I worked with them to create a template for the perfect hat box. I needed it to be collapsible because I didn’t have a lot of room to store the boxes. I wanted it to be a unique shape to stand out and, so, we went with hexagonal. Then I thought: Why not create three hat box sizes to fit three of the most popular hat styles I sell?

All my hat boxes were made with the Formé Millinery logo, and I felt it really added an additional element to my brand. They were sturdy, made of recycled materials, and made in the USA. People bought them whether they bought a hat from me or not. This got my husband, Bart, thinking: If you were having a problem getting hat boxes, then surely other people or companies are, too. Why don’t we start a hat box company?

And in 2017, Hat Boxes USA was born to fill a void in the market. We understood the challenges associated with finding quality hat boxes to accommodate the large array of hat sizes and styles — and we knew the importance of protecting these heirlooms. Bart took on this challenge and started the business in the basement of our home. Boy, do hat boxes take up a lot of room!

We decided to put them for sale on Amazon. Initially, we were just hoping to cover the Amazon fees. In the first month, we were able to pay our fees and then some. We were selling hat boxes faster than we could have them produced. Wayfair then reached out to us and wanted to sell our boxes under their name. Just as Bart predicted, not only did hat makers like me need hat boxes, but also boutiques, hotels, movie sets and travel agencies — even cruise ships ordered hat boxes from us by the hundreds.

Things were going well and we were beginning to make a name for ourselves within the hat community. Then, Judith Mishler, who owned Judith M Millinery Supply House in La Grange, Indiana, contacted us. I knew Judith because she had one of three millinery supply houses left in the U.S. I bought many raw hat-making materials from her over the years, and taught hat-making workshops at her place, which was located in the middle of Amish country a couple hours outside of Chicago.

With the pandemic in full swing, Judith was looking to retire after almost 30 years in business. She knew Bart and I were heavily involved in the hat world and asked if we would be interested in taking over. We certainly didn’t want to see her close, like so many other hat companies had done over the last 10 years. So, we thought: Well, we are in the middle of a pandemic … it is probably difficult to get a loan right now … we don’t know when all of this will turn around … yes, let’s go for it!

People thought we were nuts. So did we, frankly, but we were going to see if we could make this work. The signs were already pointing in our favor because we lived in La Grange, Kentucky. So, we packed up Judith M in La Grange, Indiana, and moved the business to our La Grange.

Hat Boxes USA was doing well, and we really needed to move it out of our house, so we decided to open a storefront in our little historic town for the new headquarters for Hat Boxes USA and Judith M Millinery Supply House. We kept the original name of Judith’s business, her website, and even phone numbers. She had created such a name for herself in the industry and we wanted to continue her legacy.

Bart now runs our La Grange store. We sell all the raw supplies to make a hat from scratch — any material you can find from across the globe. We sell to the millinery and costume departments of Disney, Warner Bros., opera houses, universities, etc. The store is open to the public, so we also get hat makers who come visit us to see the supplies in person.

Just when we thought we had created our own little happy hat family and everything was going well, a big uproar occurred in July 2023 in Louisville. A local craft store that had been in business for 52 years was closing. It specialized not only in home goods, but also had a big business during the Kentucky Derby when they decorated hats for people.

When I say big business, I mean BIG. I mean: They sold roughly 4,000 hats from March to May. Now, their hat business was very different from Formé Millinery, where I create hats from scratch, and from Judith M, which sells raw materials. This craft store sold hats that were already made, but not decorated. They sold every hat base shape you could think of, and feathers, flowers, ribbons, etc. People would come in, pick out a hat base, and then select all their embellishments and either glue it together themselves or have the shop’s designers do it for them. The shop turned completed hats around in a day.

With the store’s imminent closure, people literally went into a panic. The hats there were sold at a particular price point that was less than a truly custom hat and appealed to a large market. Bart and I thought we needed to do something. If someone was going to step into this market and save the “hat” day, we were the best pair to do so. We had already established relationships with the manufacturers who make the raw materials so we could just work with them in a dif- ferent way and have them make hat bases for us, too.

During this time, we knew we would need a storefront that would have a lot of foot traffic like the craft store did. We even considered moving into the old store, but it was in much need of repair.

We found a wonderful place within the same area in an outdoor mall that also had JOANN, Trader Joe’s and World Market. This was a perfect place and great size (our biggest store), but very expensive. The landlord was not willing to do a pop-up shop, only a three-year lease — at the minimum.

To make this work properly, we needed to be open by the end of the year to work out all the kinks before the Derby rush. This was certainly going to be the biggest (and most expensive) business decision Bart and I had ever made. We decided to bite the bullet and take the plunge: We opened our third store, The Hat Shoppe, on November 10, 2023.

It’s a full-service hat shop with, of course, Derby hat-making supplies and hat bases ready-made for decorating, along with feathers, flowers and ribbons, plus we have a men’s hat lounge and a hat bar where you can make and brand your own felt hats. We also conduct hat-making workshops of all types and bring in guest instructors. We still feel very new, and this store does operate differently than Formé and Judith M, so we are still working out all the kinks (of which there have been many). With a three-year lease in our future, success is our only option.

It has now been 17 years since I started making hats in my basement in Chicago. I am a five-time Featured Milliner of the Kentucky Derby. I make ongoing hat collections for Vineyard Vines, J. Peterman, Keeneland, and Brown-Forman, to name a few. I am also a hat designer for McCall Patterns and the author of the book The Making of a Milliner. My hat clients include Oprah Winfrey, Madonna and Barbara Cochran.

At the end of the day, Bart and I come home to more gray hairs. Amelia is 8 years old and has grown up in the world of hats and entrepreneurship. She has her own little corner in every shop that is her happy place — when she is not playing with the feathers or helping customers. If you are in the Louisville area, come see us. Try a hat on, buy a hat, or experience one of our hat workshops.

Regardless, always make it a hat day.

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