It is perfect Pamela-style and will be worn often
In terms of collars it is mostly spread collars (I have a narrow face and use every opportunity to wear a tie), some button down for more casual dressing and a point collar for more formal events maybe
As a general rule, I find that pairings that show no skin (see here and here) and a little skin (see here, here, and here) work best, as opposed to sweater dress looks that expose a significant portion of your legs (see here)
These adorable dresses were inspired by nostalgic prairie life/Old West/ frontier days but with the short 60s hemline
WHERE TO WEAR: Pretty date nights, romantic dinner dates, champagne with the girls, bottomless brunches, garden parties, vacays