Drop waist dress + striped espadrilles
ASOS dress sz 2P (similar options below), Celine luggage tote in nano Soludos espadrilles sz 5 (25% off, price matched at Nordstrom)
This is my second dress in the drop-waisted style...the first one I experimented with was back here and I initially had mixed feelings, but ended up absolutely loving it after shrinking that dress in the dryer. Shrinking brought both the hem and dropped waistline up several inches so the dress fit more like a tunic, which made a big difference visually (wish I had an "after" photo!). I think a key to shorter ladies pulling off this style is to keep the waist undefined but make sure the length is short and shows off most of your legs. This will help balance out the lack of a true waistline, which usually marks the visual beginning of the leg line. I prefer my pieces with this silhouette to hit around the upper thigh - pairing it with flat or lower shoes will help keep that length from feeling too hoochi!
Alterations tip: to get dresses like this to hit at your optimal length, try either shortening the shoulder straps if sleeveless, or, have your tailor remove the bottom ruffled hem part from the dress and re-attach it at the best height (rather than hem length off the bottom of the ruffle). Here is a drop-waisted dress I borrowed from a friend that was altered to fit a shorter frame.