I don't mind others wearing seasonally confused styles. Well, in fact, I often find them fascinating, fun, even hilarious. But I realize that people likely have their reasons for dressing the way they do, and that some of the reasons might be related to health and body issues.
As for myself, I feel a need to keep my neck and shoulders warm year round, so even in hot summer you will often see me wearing a scarf or shawl. But apart from that, I don't think I tend to wear seasonally confused outfits nowadays.
When I was in my late teens, however, I actually tried to kind of ignore the seasons. So I would wear i.e. a long wool coat in summer, thin nylons or thin white cotton pants in freezing winter, open shoes on rainy spring days, and thin silk skirts on windy, cold fall days. Neither practical nor comfortable.
Over the years, I have felt a growing need to live in harmony with the seasons and have become increasingly interested in reflecting them in my clothing, food, activities, etc. Harmony means a lot to me, in all areas of my life.
I have favourite colours, styles, and jewellery for each season. They are not forced upon me by others, but are careful choices made by me. I certainly do not feel that those colours, styles, and pieces of jewelry are the only ones I can wear in the actual season. But to me, it brings joy to subtly reflect the actual season in my outfits--like wearing gold jewelry in spring (to reflect the sun), wearing cool colours like blue, torquoise and white on hot summer days, sporting cozy knitwear in fall, and wearing velvet and other shiny fabrics in dark winter.