I'm probably the most vehement seasonal confusion fulminator on here, so I apologize, to Brooklyn and anyone else I may have put off -- completely unintended and I'll try to mind my tongue in future.
Having moved to a new climate, I see in a new way how what is seasonally confusing (just as what is appropriate in other ways) depends to a huge extent on climate (obviously!); an individual's specific work/ roles and where those are performed; whether or not a person runs hot or cold, etc.
What was seasonally confusing (and downright stupid) in my old climate is sometimes just the thing in my current climate. Workhorses here were "barely worn" items there. And so on.
Echo, for give me if I'm wrong, but don't you live in the northeast? If so, turtlenecks and sleeveless can definitely feel a bit off -- but they can also work really well for specific situations -- cool summer nights (with a denim jacket or other topper -- and yes, that's totally okay with a dress like this!); when you are in not-so-arctic AC, if you run medium, neither hot nor cool; days when there is less humidity in summer and/ or maybe cloudy days.
I don't have a dress like this but I used to put together similar outfits with sleeveless turtleneck tops and a tube skirt. I wore this kind of combination a lot -- dressed up or down -- when I lived in Ontario. I haven't been wearing my sleeveless t-necks much lately, but I still have them because they're useful items.
I love that dress for its ability to skew casual or dressy depending on how you style it.