Sleepy Hollow Country Club Headless Horseman 2023 Imperial Golf Hat Tillie Rare

A truly unique and exceptionally hard-to-find piece from one of America's most prestigious golf clubs, this Sleepy Hollow Country Club Headless Horseman hat celebrates the club's rich history and architectural legacy. Produced by Imperial for the 2023 season, this navy performance golf cap features a one-of-a-kind embroidered Headless Horseman logo that cleverly incorporates the iconic "Tillie Head" caricature of legendary golf course architect Albert Warren Tillinghast.

For golf architecture enthusiasts, the detail is remarkable. The smiling head atop the horseman is a tribute to Tillinghast's famous caricature, affectionately known as the "Tillie Head," which has become synonymous with some of America's greatest Golden Age golf courses. Similar versions of the Tillie Head can be found at renowned Tillinghast designs and destinations including Asbury Park and other historic golf landmarks, making this hat especially desirable among architecture collectors and club memorabilia enthusiasts.

Founded in 1911 overlooking the Hudson River, Sleepy Hollow Country Club is widely regarded as one of the finest classic golf courses in the United States. The course was originally designed by C.B. Macdonald and later refined by Seth Raynor before extensive restoration work returned many of its legendary design elements. Today, Sleepy Hollow consistently ranks among the Top 100 golf courses in America and remains one of the most exclusive clubs in the country.

The front logo combines Washington Irving's famous Headless Horseman imagery with patriotic details and the Tillie tribute, while the rear embroidery features "Headless Horseman 2023." Manufactured by Imperial, one of golf's most respected headwear companies, the hat is constructed from lightweight performance polyester with an adjustable strapback fit.

Details:

* Brand: Imperial
* Club: Sleepy Hollow Country Club
* Event/Theme: Headless Horseman 2023
* Color: Navy Blue
* Size: One Size Fits Most
* Adjustable Strapback
* Performance Polyester Construction
* Embroidered Front Headless Horseman Logo
* Features Tribute to Albert Warren "Tillie" Tillinghast
* Embroidered Rear "Headless Horseman 2023"
* Lightweight Golf Performance Fabric
* Made in Bangladesh

Condition:
Excellent pre-owned condition with light signs of wear. Clean throughout with strong embroidery and vibrant colors. Please review all photos carefully for condition details.

Treasure Hunter's Note:
This is one of the more unusual and collectible private club golf hats we've come across. Combining Sleepy Hollow's legendary Headless Horseman identity with the beloved Tillie Head tribute creates a piece that appeals to both golf architecture enthusiasts and collectors of elite club memorabilia. Given Sleepy Hollow's exclusivity, Top 100 status, and the limited nature of club-issued merchandise, opportunities to acquire hats like this are few and far between. A standout addition for collectors of Tillinghast, Macdonald/Raynor, or premier golf club memorabilia.