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.