For decades car makers have used hubcaps as a way to promote their brands, so it's not surprising that Willys-Overland and Willys Motors also did that, specifically with W-Os and Ws. Now, I'm most definitely no hubcap expert, but I'll take a stab at this anyway based on some Google searches (what could go wrong with that?).
In Willys-Overland's case, one of the earliest examples of the W-O branding appearing on a hubcap was this 1932/1933 Overland 8-88s:

From this page: http://www.wokr.org/gallery/wil_hc_09.htm
By 1939 (possibly earlier), the Willys-Overland sedan was sporting a more familiar arrangement, a large W over a broken O:

This 1939 sedan has a set: https://www.mecum.com/lots/AN1116-260766/1939-willys-overland-sedan/
Based on that hubcap, we can also date the original version of this sign, which pops up on the internet quite frequently, to the late 1930s:

In 1940, Willys changed it up to show WILLYS in all caps:

http://www.wokr.org/gallery/wil_hc_32.htm
For the 1941 Willys Americar, the company created a much fancier hubcap:

From this page: https://www.jalopyjournal.com/forum/threads/sold-nos-41-willys-hub-cap.1074070/
After the war, Willys-Overland introduced their new 473 wagon with a riff off the 1939 hubcap, a W over a broken O with the letters about the same size:

http://wokr.org/gallery/wil_hc_47.htm
In mid 1947, the company introduced the Jeep Truck. The jeep truck sported a new Willys logo, a W-over-an-O design, with the W larger than the O, on the truck tailgate, as seen in this introductory ad for the truck (and would be manufactured with the embossed tailgate through 1953).

I expect that the hubcaps on the wagons were changed over to the newer logo, but I lack a specific date for that. It seems logical that by the time the Jeepster was announced in 1948, that all the hubcaps would have sported the new W-over-O design, shown below. (though, some 1948 ads for the wagon still showed the older design ... 2WD wagons would use this hubcap design through 1964, as best as I can tell):

https://www.flickr.com/photos/geepstir/8115007284
It was also in 1948 that ads began appearing with the same Willys-Overland logo, as part of the City to City ad campaign, mentioned in this long post.
In 1951, Willys-Overland shifted to a Willys-centric marketing strategy, as part of an attempt to put both jeeps and cars under one umbrella brand, as seen in the 1951 Willys Makes Sense campaign.
From here, the story continues as Willys continues it's shift from Jeep to Willys with the introduction of the angular W logo (post below this one).
BTW, I doubt that this is a complete list of Willys-related hubcaps, so I welcome corrections for those that know more about this than I do!



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