One of the coolest retro-style caps is the pillbox cap. Popular during baseball’s infancy in the late 1800s, the pillbox cap is a ubiquitous look and stands out compared to the average ballcap. Though somewhat of a misnomer (actual pillbox caps lack a brim), the pillbox name has stuck to the baseball style of cap that has a boxed, round look around the crown of the cap with a flat top. The Ideal Cap Company has an excellent visual guide to the various styles of older baseball caps. For our purposes and for familiarity’s sake the following cap is referred to as a pillbox cap.
Yellow pillbox crown and brim
Brown soutache (piping), squatcho, and ’69-era interlocking SD
Brown and yellow New Era logo
Part of a Cooperstown collection release circa 2010, this cap makes great use of the classic brown and gold colorway as a pillbox look. The brown squatcho on top of the flat crown is merely a decorative touch compared to the average squatchee on a regular 59Fifty. The pillbox is also not referred to as a 59Fifty since well…it’s a pillbox. The 59Fifty moniker is reserved for the standard on-field 6-panel style of cap New Era produces.
The rear of the cap features the MLB Batterman logo in white, brown, and yellow with a brown border. The beauty of the pillbox is in its lack of seams compared to a regular cap; only one seam for the entirety of the rounded portion of the crown is found at the rear.
The underbrim matches the rest of the cap as yellow; the sweatband is black. OF note on the inside of a pillbox is the lack of a buckram. Generally pillbox caps are considered “crushable” crowns, or crowns with no horsehair buckram to maintain the shape and integrity of the crown.
Here’s a better look at the interior “New Era Fits” taping and tagging. My example is a 7 7/8, a size considered a bit of a unicorn in the collecting world. Not many caps are made in a 7 7/8; those in between a 7 3/4 and an 8 either go for one size or the other. Being a 7 5/8-7 3/4 wearer this cap is actually a perfect fit; the pillbox cap is markedly shallower and runs a bit smaller than a normal 59Fifty cap. The looser fit allows the cap to sit on my head properly without literally sitting on top of my head.
Cap Availability Status: Grail
The cap pictured here was a generous gift from @tonylosoya in his eBay browsing. Your best bet for this version of the cap is eBay as well. I haven’t seen another example of this cap since acquiring it.