All I have been able to find out is it is a bucket hat but as to how old it is I have no idea.

In 1928, David Warsaw founded Sports Specialties Corporation, which was the first company to sign a licensing contract with a professional sports team. While creating and manufacturing sports souvenirs at his Chicago-based company, he came up with the idea for ashtrays in the shape of Wrigley Field and selling them to Cubs fans. He approached Cubs owner Phil Wrigley for permission to sell them at Wrigley Field and won him over when he agreed to pay him a “royalty” on every ashtray sold. As his business grew, so did his ideas. In addition to the ashtrays, David patented a miniature ceramic baseball player, whose head bounced on a small spring. Today, this doll is known around the world as the “bobble-head doll”.
David’s sons Jim and Robert entered the family business. Together the Warsaw family grew Sports Specialties into the world’s leading licensed sports headwear company. In 1963, Sports Specialties became the first official licensee of the National Football League and was the first to be named as an official championship locker room headwear supplier for special sports events such as the Super Bowl, NBA Finals, All-Star Games, and the NCAA Final Four. Now base out of Irvine, California, Sports Specialties secured the first “Authentic” license agreement in professional sports when the NFL “ProLine” was created in 1984. They became an official licensee of Major League Baseball that same year, entering the on-field professional model cap market, competing against New Era Cap Company and Roman Pro Cap Company. Sports Specialties took the place vacated by Wilson Sporting Goods, which had just left the on-field cap market.
Early 1980s Sports Specialties caps

The company’s signature 100% wool sized caps, called “The Pro” (their equivalent to New Era’s 59/50), were the first contracts for “on field” authentic headwear for the NFL, NBA, NHL, Major League Baseball, and the 1992 Olympic Basketball Dream Team, as well as more than 80 countries in the International Baseball Association. Sports Specialties was bought by MacGregor Sporting Goods Inc. in 1986 and was sold by late 1987 to the Oppenheimer-Palmieri Fund L.P. Their caps were used by several Major League Baseball teams throughout the 1980s, giving New Era a run for their money by the end of the decade. More than half of the MLB teams used their caps for at least one season. Around that time, Sports Specialties and New Era were granted dual exclusive licensing for MLB caps, making them the only two makers of on-field professional model caps under the “Diamond Collection” label (Roman Pro and ANNCO were granted dual exclusive licensing under the “Cooperstown Collection”). During the 1989 World Series (between the Oakland Athletics and San Francisco Giants and when the famous earthquake struck) both teams were wearing Sports Specialties caps.
Sports Specialties caps were not made in the United States. They were manufactured by the Young An Hat Company in Korea, which still exists today but no longer makes ballcaps. Their caps were later made in various South American and Asian countries. Sports Specialties caps are recognizable by their thick wool, flat as possible embroidery, and short, narrow visors. Their sizes were also sometimes one to two times larger than New Era’s sizes.

Well, one clue is the NFL official licensing logo, which means it’s post AFL merger with the NFL. I believe the merger was finalized in 1970, but they began merging legalities a couple years or so before 1970. I would tend to think the licensed retail merchandise was sold once the merger was finalized, due to legalities, but not sure.

The logo attached appears from the photo to be genuine wool felt, if so, that indicates to me the hat was manufactured pre 1980’s, which during the 80’s imitation felt began to replace wool. However, if the manufacturer was considered one of high end, best quality…they could’ve still used genuine wool felt.

The text style also indicates to me the 70’s, but again…it’s hard to say for sure.

You might try searching and watching Ebay to see if one similar is listed, sometimes the seller is the original owner of a vintage item listed and will give a history, including age.

try VillageHatShop.com, they claim to be experts on unique hats maybe they can give you info and value

I’ve collected Chiefs memorabilia for almost 30 yrs…but I’m partial to vintage memorabilia. I’ve not ever seen another hat like yours. I don’t think it’s ‘homemade’ because of the tag. I doubt it’s 1963, because the Chiefs weren’t part of the NFL in 1963, so their merchandise from pre-NFL merger era didn’t have any tags related to the NFL.

I’m still thinking it’s an early 70’s era hat, based upon style, felt logo, and the NFL licensed merchandise tag.