Hats Off To The Horses - The Mr. Cowboy Hat

Special thanks to TV analyst at Gulfstream Park and former Miss Connecticut, Acacia Courtney, for helping us by modeling this lovely hat!  Thanks also to Connie Bush of Tiger Eye Photography for her stunning images of Acacia and Mr. Cowboy.
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 The Ninth Annual "Hats Off to the Horses: The Road to the Derby"

 A Unique Online Derby Hat Auction Benefiting Old Friends  
sponsored by MAGGIE MAE DESIGNS® - Custom Derby Millinery by Sally Faith Steinmann

For the ninth consecutive year, MAGGIE MAE DESIGNS® of Cape Cod and Old Friends of Kentucky are teaming up again for an unparalleled online shopping experience with their Hats Off to the Horses: The Road to the Derby" auction.  This unique Derby hat fundraiser is an annual event which features one-of-a-kind couture Derby hats created and donated by custom milliner Sally Faith Steinmann of MAGGIE MAE DESIGNS® to benefit the Old Friends horses.

Our first eight years of the fundraiser have been a great success, and to date over $33,000 has been raised for the retired racehorses of Old Friends.

The third Derby hat up for bid in our 2018 auction series honors New York-bred, Mr. Cowboy. The 8 year-old son of Stonesider is perhaps best known for his thrilling victory at Saratoga on August 26, 2012.  This hat auction will end on March 11th at 8pm EST.


Mr. Cowboy retired in 2014 to the Old Friends satellite farm, Old Friends at Cabin Creek. 

JoAnn Pepper of Cabin Creek Farm, describes Mr. Cowboy in the following way: “Mr Cowboy is one of the most entertaining horses I know. For a small treat he will race anyone, anytime. He also entertains himself well with his jolly ball and road cone. He's very lovable and we are thankful he's in our lives!”

The fact that Mr. Cowboy is alive and well today is a miracle, for he was not breathing when he was born during the wee hours of March 15, 2009 at Cabin Creek farm. The owner of what was a boarding farm at the time, JoAnn Pepper, gave the tiny chestnut colt human-to-equine resuscitation which soon revived him.

A long period of recovery followed for the little colt that JoAnn named “Mr. Cowboy”, while another resident of Cabin Creek named Moonshadow Gold became Mr. Cowboy's guardian and mentor.  Mr. Cowboy grew strong as a yearling and eventually went into training with Bill Allyn; racing under the partnership of Team Cowboy which included Mark and JoAnn Pepper and many of the volunteers of what had since 2009 become the Old Friends satellite farm, Old Friends at Cabin Creek – the Bobby Frankel Division.

Mr. Cowboy had a big win in the summer of 2012 at Saratoga for then-trainer, James Bond. In an August 27, 2012 Bloodhorse article Bond was quoted as saying, "There are miracles in this world, and I think he (Cowboy) was a miracle. But the biggest miracle is he got to be with Mark and JoAnn. They believed in him and they never gave up." Bond also spoke in the article about the colt's good fortune having Team Cowboy in his corner:"It was unbelievable to see all those people (in the winner's circle), who are so respectful of the horse and his time. I hope they all had as much fun as I did, because they sure seemed to. Their hearts are really in it. They really love the horse."

A minor injury in 2014 resulted in Cowboy heading back home to Cabin Creek where he has been enjoying a happy retirement since then, surrounded by all those who know him and love him.  Read more about Mr. Cowboy by clicking here.

Clearly, a very special hat was needed to honor this beloved retiree of Old Friends at Cabin Creek. The resulting hat design showcases Mr. Cowboy's bright chestnut coat, his yellow and green Cabin Creek racing silk colors, his buddy Moonshadow Gold and his bloodlines.

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The foundation of the design was created with a strong Western flavor to reflect his dam, I'm a Cowgirl, and dam sire, Western Expression.  Fashioned out of deep yellow dupioni silk, the hat is shaped with a fedora-style crown and upturned “cowboy” style brim.


A thin strip of fancy dark green braiding top stitched to a band of chocolate taffeta along the brim edge gives the hat a finished look.

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For the trim centerpiece a single large rose was sculpted out of swirling layers of chocolate organza and dupioni silk and placed along the front crown of the hat. A shiny gold star black button was stitched to the center of the rose.  The rose was then framed with a medley of emerald green dupioni silk leaves with chocolate braiding loops.


Fabric “feathers”, a MAGGIE MAE DESIGNS® trademark, were fashioned in varying sizes out of chocolate organza lined with golden yellow organza and layered and shaped to add a splash of dramatic detail to the floral trim.


Stunning, from every angle!

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Continuing the Western flair a unique sash was created out of braided chocolate and emerald dupioni silks, and placed around the crown of the hat.


A large brassy colored button with a spiral design was added to the back of the hat for the finishing touch. Along with the gold organza-lined feathers, this button is a tribute to Moonshadow Gold, the horse whom JoAnn Pepper describes as, “The one who raised Mr. Cowboy”.


The lining for the “Mr. Cowboy” hat was created from a rich brown satin to coordinate with the trims.

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The finished “Mr. Cowboy” hat design measures approximately 16 inches across, exclusive of the silk “feathers” which extend approximately 10 inches over the brim.   As a physical remembrance of Mr. Cowboy, several strands of his tail hair were braided and woven into the trim of the hat, creating a unique, one-of-a-kind Derby chapeau that captures Mr. Cowboy not only in spirit but in substance as well.


Many, many thanks to TV analyst at Gulfstream Park and former Miss Connecticut, Acacia Courtney, for helping us this month with our “Hats Off to the Horses” fundraiser that supports the retired racehorses of Old Friends in Kentucky.  As always, we thank our good friend, Connie Bush of Tiger Eye Photography for her stunning images of Acacia and Mr. Cowboy.

"Sally Faith Steinmann's works of millinery art have raised thousands of dollars and a priceless amount of awareness for all these great retired athletes. Their stunning beauty and indescribable originality symbolize what one great artist can do to positively alter the lives of so many deserving athletes."- Michael Blowen, President, Founder of Old Friends. 

Bid as many times and on as many hats as you like during these auctions. For further information about the eBay bidding process, please contact Old Friends at 502-863-1775.  Freight charges will be at the expense of the winning bidder. Please allow 3-4 weeks for delivery of your hat in order to ensure proper sizing.  To view the couture Derby hats from previous auctions, please click on the following -

View MAGGIE MAE DESIGNS® information page about this hat.

Old Friends Hat Auction Portfolio.



Once again, we thank our participants in the MAGGIE MAE DESIGNS® presents
''Friends of Old Friends'' social media campaign - help us out by sharing the love!

Please join me in thanking all of the wonderful organizations listed in the above poster who have joined us this year as “Friends of Old Friends” to help spread the word about our “Hats Off to the Horses” fundraiser.  To read more about this new social media campaign, please click on the poster or this link to learn more!

All hat designs and hat photos on this page are the sole property of MAGGIE MAE DESIGNS®. All Images and content may not be reproduced for any commercial purpose without the express, written permission of MAGGIE MAE DESIGNS® or the photographers noted.  Copyright MAGGIE MAE DESIGNS®


Learn about this fundraising project for Run In Sheds - Click here