Hats…Yachting Hats. Captain’s Hats. Skipper’s Caps…A Tutorial


Greg Jones, and his hats are here to edjumacate us.

You may want to make a large cup of Varnish Coffee today. Mother of God, today is the ultimate hat story. I asked fellow Woody Boater Greg Jones to send us a story on his hat collection. Oh! Ya! He delivered.. oh he delivered.. It’s a fun read, and even more fun to look at all the classic boating hats. And shockingly, Greg looks normal in these hats. I can never pull it off. But he sure can. So without adding more stuff you need to read. Take it from here Greg!

Note.. He has been banished to the basement. Thats the sign of a true collector

Can we all agree that his bride is “done” with the “hat thing”

You asked for it…you got it. Hats…Yachting hats. Captain’s Hats. Skipper’s Caps…a tutorial

I was raised in the 1970’s and they were everywhere. K-mart, Sears, sporting goods stores, mail order, and marinas. TV had them on Captain & Tennille, McHale’s Navy, and of course that little show about the castaways…

I digress.

They were for whatever reason a sign of being rich, authoritative, or leisure to me I guess. I wanted one. Everyone had ball caps. I guess I needed to stand out.

We are all a little Dinghy. LOVE THIS PHOTO

So mom and dad likely bought one for me at the department store. Then Dad worked at the airport and bought one of those “Junior Captain” pilot hats at the gift shop. But these were flimsy and inexpensive and lasted a few months before they were worn out. Finally being a lousy student, Dad hatched a plan to bribe me to do better in school. He went to the Army & Navy Surplus store and bought the real deal! A bonafide Captains hat with black sweatband, white top and gold embroidered patch. I was promised if my grades improved I would be given the hat.

So the school year trundled along…no improvement. After a while I suspect my folks just gave up and by summer they wanted it out of their bedroom. Alas I was given the hat. I lasted about a year.

1940’s dinghy. Thats alot of hat for that little boat!

So as I got older, high school came along and hats went away as it was more important to be “cool”. Some time after high school I was playing trombone, and could never play the damned thing quietly. So I needed a way to quiet things down on a ballad. Bucket Mutes are clunky and heavy. Cup mutes are too restrictive. Plunger mutes have to be held over the bell and leave your arms feeling like MaGilla the Gorilla. So I needed something quickly accessible…and something I would be able to find if I might…have…a…drink on the bandstand. So the Captain’s hat fit the bill. Pop it off…hang it on the bell…return to head when done.

So yes. It became my thing. People fought and lost their lives for us to live as we wish and thus I wear the damned hat. I see many folks wearing sports teams hats who have never played a day in their life. At least I’ve owned and restored 11 boats.

Greg and Remy.. Next pooch should be called Tennille .

More amazing when we are out, I get the rare Captain and Tennille remark, but generally people stop us to make favorable comments. At the fast food drive thru, the grocery store, the meat counter. On and on. Maybe people are starved for fashionable headwear.

Marshall Fields hat

Department Store Hats

These are on the inexpensive side. The Han-Kraft Flyweights are at the top end of that spectrum. The unknown Khaki hat in New-old-stock and made in Louisville with no indication by whom. The Imperial is more typical of the Sporting Goods Store. And the cheap blue one is interesting in that I was told by Trombonist Grover Mitchell who was Count Basie’s 2nd in command near the end of Basie’s life…Grover would be sent out to buy hats for “the Chief”. But “Chief” didn’t want to spend much money, so this was typical of the hats Mr. Basie wore.


Abercrombie and Fitch

Search the internet and you will find similar caps on his album covers or publicity stills. The Forty Fathoms and Columbia Sportswear hats are nicer department store hats and look for all the world like the famous Lancaster hats. They are pretty rugged too, albeit light-weight in construction. These get favorable comments for whatever reason.

I used to wear the Columbia Sportswear hat often during election season. I looked up the manufacturer and they are around and still producing ball caps. In fact they produced the infamous MAGA Hats, so I wore this when I was around non-MAGA types. Not because I liked HIM…but I thought those folks were childish acting in such a way toward a hat. So this was my little undercover protest. SHHHHHH!

So there are also many manufacturers of what I’d term intermediate caps. These are a step above the department store hats, but not quite at the Lancaster Cap Co. grade…which for me is the Holy Grail and measure of all hats.

1930’s Unknown Crusher Cap

So here we go!! A step above the department store hats

The Unknown Crusher is designed after the popular 50 Mission Pilot cap. It can be rolled up in a duffel or stored without damage by cramming it in where needed. This Abercrombie and Fitch cap is pretty much Identical to the hat Humphery Bogart wore in “To Have and Have Not”. This insignia is embroidered into the band braiding. This is kind of unique.

Art Caps Yachting Hat

The Art Caps is just a typical, but good example of a nice medium-grade cap as is the next one from Kerr’s Sporting Goods.

Kerr’s Sporting Good White Yachting Cap

Their stores were on the West Coast and this hat is actually waterproofed on the fabric. The Kingform was worn by a senator or congressman in the Michigan political circles. That may explain the 7 5/8 sizing. LOL! And last the Marshal Fields hat is just a nice example of a removable wool cover on a frame for cleaning purposes. It’s in quite good shape, though the visor needs to be softened.

Kingform Yachting Cap

Bored yet!?!?!? Who knew there were so many styles of hats!?!?!?

We now are migrating toward military spec or professional grade hats. These are hats that tend toward the formal and or military style with a frame, chin strap, removable cover, and band with insignia.

Commodore White Captain Cap

First is the fact they are all military spec caps manufactured by companies who provided hats to the Army, Navy, Air Force, Marines and Coast Guard along with that they saw an opening in the yacht club market.

Commodore White Yachting Cap

The first is from Commodore with an beautifully embroidered visor and insignia. Love that gold bullion wire!! The 2nd Commodore is New-old-stock in the bag and comes from a yacht club in Northern Ohio, but was found in an antique mall in Springfield Ohio 150 miles away…for the princely sum of 35.00. Its near perfect and denotes the Yacht Club Rank of Commodore with the three stars around the fouled anchors.

Joe Harris White Yachting Cap

Next is a Joe Harris of San Francisco Cap that is again military grade and the three silver stars denotes Past Commodore. The same is true of the S. Appel Co. of New York, NY. Nice example with some slight staining from age.

S. Appel Co Yachting Hat White

We are getting to the Holy Grail of caps next. Two manufacturers made the hats we are most likely to see on on tv shows and movies. They are Midway Cap Company and or course Lancaster Cap Company.

So now we get onto the hats everyone loves and has seen in a million movies. Midway Cap Company is still in business in Chicago and makes a nice cap for not too awful much money. They are not as comfortable as a Lancaster Cap, but Lancaster is no longer in business. However thankfully Matt and the Woody Boater blog managed to get one last run in before the doors closed the final time. I missed the opportunity to buy one at that time, but found some Woody Boater abandoned his cap on eBay…and I snagged it.

Midway Aristocrat

So let’s start with Midways caps. Midway is Chicago based and still makes hats on request. They are around 75.00 or so bucks last I checked. They are nice with removable covers for cleaning and come in blue or black and white. They also make a mesh version for hot heads at the launch ramps.The Aristocrat is still made, and the “Unknown” is I suspect a Midway contracted cap for a store dating from the 1950’s or 1960’s given the short visor.

Lancaster 2014 Last Run

And the Lancaster Caps are the best and most comfortable if worn. The Black cap from the 1990’s is probably due for retirement. It has been my goto cap for years…and still fits like a glove, so I’ve had a hard time not continuing to press it into service. Next is a second job I had Lancaster do for me. I added the insignia…and again…it has been well used.

1990’s Lancaster Standard Yachting Cap

The Lancaster Standard White cap is one I ordered with the black cap. They both were 75.00 at that time in 1996 or so. The next custom cap by Lancaster is one I had them build with the Admirals visor using the gold bullion wire embroidery. I added the insignia and this hat is used and abused, but never seems to never fail to get a favorable comment. I guess beauty is in the eye of the beholder. It fits great and is getting raggedy and should probably be retired as well. It is nearing 25 years old.

Captain’s Locker – Lancaster Cap – Sprayweight

The next two are from Captain’s Locker and are house brands made by contract with Lancaster. The shape and style is certainly close. But the construction is of a lesser quality. That is typical of contract work. No one makes the best hat under a name other than the “marquee brand name”. Outboard motor manufacturers did the same thing.

Joe Harris – Lancaster Cap

Next the Joe Harris Co. hat is contracted by Lancaster and is similar to one worn by Elvis. This one is New-old-stock as well and at one time had a yacht club insignia inside the life ring. It is near immaculate and was built in the 1960’s is suspect. The next Lancaster is BLUE! It was one I snagged of eBay and was run with the last from the Woody Boater run before Lancaster closed up shop.

Lancaster Open web

And finally…the Super-Duper-Holy Grail is this Lancaster hat with the open weave headband. YES! This was made at about the same time as Alan Hale Jr’s cap for that show. This can be identified by the cut of the cap and the insignia which varied over the years. I wear it sparingly, and never in a dirty environment if possible as these are probably the most scarce hat made by Lancaster. BTW it is also featured on the head of Captain Daryl Dragon on that album containing “Love will Keep Us Together”. (That didn’t really work out so well…did it?!?!?”

2000’s Lancaster Custom

Now most of my Lancasters are well past 20 years old and going strong…so I would say money well spent. I will likely not have to buy another to get me through the end of my life…so I wear them. I enjoy them especially when out in our 1958 Lyman running the Ohio River. It’s part of the package. Folks really respond to it…”aboard ship” or on land.

1912 Vintage S. Appel Co Yachting Cap

My three oldest caps are a vintage 1912 cap from S. Appel of New York City. It features a very early yacht club burgee in enamel for a now defunct club in Manhattan. The next is an unknown probably from the 1920’s.

1920’s Unknown Blue Yachting Cap

It is tired and needs a new sweatband inside. The headband is made of cane and the stitching on the insignia is awful, but original. Lastly a late 1920′ to early 1930’s cap from E.J. Willis. This hat’s age is based on military caps of the era.

E J Willis Co Yachting Cap

And last a few photos of the hats in use.

Hope I didn’t bore you, but there is a lot of history here to be told. It’s all part of the classic boating hobby. We restore, over-restore, and are stewards of the boats, and we have a right or responsibility to not forget all aspects of our hobby. And Woody Boater does a helluva job at that, as does everyone who contributes to this blog. So thanks to one and all from Cap’ Jones. Go buy someone you love a classic hat for classic boating next season. It’s Christmas time. what could be a nicer gift.

Don’t go down with the ship Greg!

I think I sent enough for 5 days with of hats. sorry, but that is only a small percentage of my 75 plus hats I have collected. I’ll send tow quick shots in a minute of the collection


SIDE NOTE FROM MATT, I may have butchered some of Gregs story? It came in several emails, and lots of photos? AHHHHHHHHHH!

Ironically, my head hurts

33 replies
  1. don vogt
    don vogt says:

    very impressive. Do you or someone you know collect the yacht club pins that go inside the life ring? that might be an interesting follow up to this story.

    Is there currently a source for manufacturing the yacht club pin?

    • Gregory Jones
      Gregory Jones says:

      I do not collect them per se’. But they show up on hats. I think most yacht clubs that have a “formal uniform” still have them made by any company that does enamel pins. But boy oh boy some of the vintage ones are elegant.

      • Russ in Bolton
        Russ in Bolton says:

        I found a pottery shard in the woods at Black Mountain Point on Lake George, NY with an image of this burgee on it.
        I found this burgee image on Lannangallery.com without any identification of yacht club. The burgee was manufactured by Prestige Flags of San Diego.
        Do any of you have info as to the club this burgee belonged to?

  2. Gregory Jones
    Gregory Jones says:

    Okay…I forgot one. Missy made this for me a few years ago using an old visor I had laying about.

    So Merry Christmas to all…and to all a better 2021!

  3. Troy in ANE
    Troy in ANE says:


    I will need to read this over the next few days, so Matt you can take a couple days off if you want. Looks like a great read, just don’t have the time this morning.

  4. Chug-A-Lug
    Chug-A-Lug says:

    The Admiral(my wife) wants one.So she can direct me where she wants to go while sitting in her fancy dancy leather boat chair in “Chugalug”(the boat)Do I get her one with the scrambled eggs on it or knot?

  5. Greg Lewandowski
    Greg Lewandowski says:

    Great and informative story. Thank you Greg.
    I purchased this one in an antique store a few years ago for $20. Way to small for me so I will be checking out Midway Cap Company.

      • Gregory Jones
        Gregory Jones says:

        Classic cap. Looks like its based on a police cap. Amazing how people have gotten bigger over time. This 7 1/8 is probably from the 40’s or 50’s. Just a guess.

        • Greg Lewandowski
          Greg Lewandowski says:

          Thanks for the info. I never knew anything about the cap until today. I just talked to Midway and I can order one, custom made in my size, for $50.
          My uncle had one in the 60’s that he wore regularly when on his cruiser in Michigan. It was weathered and looked great. I so wish I had that cap today, but it somehow got lost over the years.

  6. Mike D
    Mike D says:

    It is interesting that there was such a demand for hats that there were so many companies making them. Any idea how they manufactured the gold bullion wire embroidery? Thanks for the story.

    • Greg Jones
      Greg Jones says:

      I don’t know the process. But I’m sure it’s tedious. But it looks amazing.

      Army Air Forces had huge patches made for their squadrons using this. True art.

      Now that embroidery is done in Pakistan or overseas. I notice that a group from Pakistan is making these hats and have stolen my photos for their EBay ads. 🤬. I’m sure they are not of very good quality. I also doubt Pakistan’s GROSS NATION PRODUCT will hinge on Yachting Cap Futures. 🤣

  7. Matt
    Matt says:

    Dont even get me started about that tool on ebay! CRAP! buy a used one on ebay or Midway. The gold boulion on my Lancaster order was done in France and took 6 months. But DAM! to be honest, the patch is kinda cooler and less formal. Now I want a crusher!

    • Gregory Jones
      Gregory Jones says:

      Matt! I’m jealous you guys had the khaki hats with a patch and the white with a patch made…and I missed it!! Very cool styler and simple.

  8. KM
    KM says:

    A great collection! Some of your followers may not be aware that the gold braid on the peak is sometime referred to as scrambled eggs!

    • Mark in Ohio (sometimes da U P)
      Mark in Ohio (sometimes da U P) says:

      Cool story Matt and Greg. Reminds me of when I was a kid and got a Captains hat as a souvenir on Mackinac Island. I thought I looked pretty cool in it at six years old. I’m sure there’s a picture of me wearing it somewhere.

    • Gregory Jones
      Gregory Jones says:

      Benford I think was contracted through Midway. But his look a little nicer. I don’t have one and wish I did. LOL! I’d like to try it. Looked like it could be a “go-to” hat for daily use.

    • Gregory Jones
      Gregory Jones says:

      Yes…but construction makes a huge difference in comfort. I have never found a cap…including a ball cap…as comfortable as the Lancaster’s once they get a shape to your head. But you have to wear them to get them there. Sweat and heat help!

      I like the cut of the Benford hats. The embroidered insignia is a nice touch and nice quality. (Looks at the variations on the insignia on hats above. Even Lancaster varied a lot over the years as to size and other details!) The chin strap is a rope with two knots, not quite like the Lancaster, but has a great styling and is classic. But I have not seen one to look at the frame. Cane…or plastic? Plastic won’t give or stretch or contour to your head as easily as cane or webbing. That make’s a comfortable difference.

      And in reality the Benford hats are not terribly priced for a nice higher end cap that looks similar to Midway or Lancaster in presentation. I just haven’t scraped up the cash for one. Maybe I should sell one of my old outboard motors I’ve restored.

  9. Dick Dow
    Dick Dow says:

    Lots of great information! Amazing what is uncovered when an interest is followed with such passion. Thank you! I suspect many will never look at Captains hats indifferently again… I have never really worn one, except on one Opening Day when I was president of the local ACBS chapter and we morphed the theme a bit. 🙂

  10. Troy in ANE
    Troy in ANE says:

    Look at that. I actually found time to read this story. Guess you need to go back to work tomorrow Matt.

    Great info Greg! Thanks for sharing.

    Here is my Father-in-Law’s original Navy hat. I suspect my Sister-in-Law has it now. May have to look into that.

  11. Chad
    Chad says:

    Thanks for sharing your awesome collection, Greg. Very informative story.

    Some guys (like yourself) look great in a cap. I am NOT one of those guys. My Lancaster sits on a bookshelf.

    My son, however, used to love his Midway cap.

Comments are closed.