It pays to hitch to the House of Heiser
The inaugural holster I'm placing here is the one that nurtured a budding interest in old leather. It has to be the first one because it holds the most sentimental value to me. It's a Heiser holster, with floral carved motifs and white latigo-laced trim made for the Colt Woodsman. My old gun club friend, Cres Lawson sold me his Woodsman, purchased new in 1928. This pistol was one of two shipped to Ad Toepperwein's hardware store and gun shop in downtown San Antonio, subsequently resold directly to William Crites of Crites gun shop just around the corner and down the block from Toepperwein's. Cres worked for Mr. Crites summers and when he was home from college from about 1926 to 1932. He said it was only gun Mr. Crites sold him for full retail, not giving him a normally generous discount and he'd always wondered why. Some 70 years later, Cres learned the rest of the story, about his Woodsman was shipped to Toepperweins, from whence Mr. Crites fetched it to fill Cres' order. Crites and Toepperwein were good friends as well as business competitors so Cres was much amused at this discovery found within the Colt factory letter I had requested.
Cres originally purchased a Brill holster to fit the Woodsman, purchased from A.W. Brill's shop in Austin, Texas. Both Cres and his father had traded there on occasion plus Cres was in Austin from 1927 to 1932 attending the University of Texas. The Brill, a holster which Cres waxed enthusiastic about, was later left in Mexico on one of the Lawson family visits to their ranch west of Cuidad Victoria. There the holster got away from him. So, he ordered this Heiser sometime later on.
The Hermann H. Heiser Saddlery Company almost lasted a hundred years, from 1858 to 1955, turning out very well-respected leather goods of all kinds. Hermann H. Heiser was born in Saxony the year of Texas' hard won independence from Mexico. He immigrated to America and by 1858 had opened a saddlery and harness business. He apparently made quality leather goods and he had a good head for business as well for the company prospered. He brought his sons into the business and when he died in 1904, they continued operating it for many years afterward. A better history than I can offer is provided in this link:
Hermann H. Heiser Saddlery Company History and Maker Marks - www.vintagegunleather.com California
No man ever lived long enough to wear out a Heiser Holster
Cres always spoke of the Heiser holster line as being
the premium line of gun leather back in the day. He did reserve a special place of top honor for the comparatively scarce Brill holsters. Perhaps this was because he traded in their shop and he and his dad knew the Brills personally. The Heiser holsters I've examined are very good holsters, made of high quality leather, near as thick as saddle skirting. No scrimpy thin wallet leather here. They are well-formed and ruggedly stitched. Though the newest Heiser is now over 60 years old now, the leather is generally found to be supple, is not found to be rotten, and the holsters remain serviceable. Any holster leather can break down when used and abused but Heiser holsters are generally found to be remaining in better condition than many more modern makers from the 1950s forward that one may see in collections of used holsters offered for sale.
Cres' Heiser holster has seen a good bit of use. I don't know its exact age but am guessing late 1930s/early 1940s. Heiser changed their maker's mark in the early 1920s and this holster features the later mark. Heiser snaps were of brass, amply large and decorated with the Heiser logo, all art deco in style, up until the late 1920s or early 1930s. It's possible to have a Heiser holster with the later style maker's mark but having the large brass Heiser-adorned snaps so there was overlap of these features for a few years in the 1920s. Later, the snaps became smaller, were of stamped steel construction, dark brown enamel painted and more simply marked "Heiser." Even later, the Heiser marking on the snaps was deleted which is the style seen here. Last style of snaps appear to be bright metal.
Heiser gun leather - Life is too short to take chances!
Cres never scrimped on what he termed "cheap-jon guns" or on accessories. The Colt Woodsman came to me in a vintage Boyt fleece-lined leather zippered pistol case. I don't know its age but am guessing it to be from the 1930 to 1950 time period. The Woodsman always lived in this case when Cres had it, the pistol carefully preserved in a coat of RIG so that's the way the Woodsman lives in my safe.

Old pamphlet advertising the Toepperwein's (spelled Topperwein in the text) Winchester shooting exhibition.