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:
By 1939 (possibly earlier), the Willys-Overland sedan was sporting a more familiar arrangement, a large W over a broken O:
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:
For the 1941 Willys Americar, the company created a much fancier hubcap:
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