I have several hundred WW2 period Air Force titles (with many shown on websites) and have made a particular study of them. There is nothing in regulations stating lettering styles and many were private purchase from tailors (most usually by officers). The style of lettering (serif or non serif) is really down to the tailor, with issue and private purchase each having both. I have BCATP issue, theatre made, British, Canadian, Indian, Rhodesian, Australian, New Zealand, South African and others and all follow the same pattern.
The construction is more of a givaway to country of origin. The BCATP for example are of a shiney thread on wool with a black cloth backing, Canadian made are usually cotton thread on wool, NZ titles are often found with newspaper backing, British are generally silk thread on wool, etc. Stiff printed (using a dark colour over a light base) are British manufacture, screen printed (light print on dark base) usually NZ, Bevo-weave generally British too, etc. I also have flocked, although their origin is so far a mystery!
Obviously there are exceptions to alll, but lettering style I have not found to be an indicator of date during wartime.
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