Our first autumnal "ways to wear" comes courtesy of some vintage catalogue and magazine cuttings. The beret is easily my favourite cold weather hat - it's very wearable, and doesn't look out of place in a modern world. As the featurelette from 1950 says, it's many hats in one.
Ideas from 1935, below, in the Sears catalogue.
A 1949 Everywoman magazine suggests different ways to adorn a beret for a variety of looks.
A featurelette from 1950, again in Everywoman magazine extolls the beret's virtues, "dressed up, flattened down; pinned with a priceless gem; padded muffin-fashion; adorned with a feather; on the back; on the front; on the side." What you will notice, though, is that these berets are slightly smaller than the standard beret size now. I've been trying (so far in vain) to find a 1950s little beret, but the styles are all still doable with a modern hat.
As an aside, this was such a transitional period in fashion that even though these two articles were published only a year apart, you can see real differences in the styling from the early New Look period to the perky 1950s.