This Elizabeth and James Zoe Square V Neck Poncho dress has a bit of a Rozae Nichols flare to it (if you are unfamiliar, this is a good thing).
I can not think of a more versitle piece (especially for$275!).
For day (transition): wear with black Lanvin ballet flats (cheapest at mytheresa.com)
For day (fall): wear with flat, black over-the-knee boots and black tights (sheer or opaque)
For happy hour/ bar casual: wear with a suede, YSL-inspired wedge
Keep this look clean with minimal accessories. Remember what your father told you: less is more.