Both pairs -- I wear the bulkier of the two on the plane -- have to multi task. One has to look good with a dress but also be comfortable for long strolls on the beach or all-day walks on city streets. And, it should also serve as a light sports shoe for cycling or low-key hiking trips. The Chaco ZX2 Yampa sandal that I blogged about recently fits the bill.
The bulkier shoe should be lightweight, comfortable for longer walks or hikes, provide good traction on the trail, be ultra breathable because my feet hate being in closed shoes to begin with, dry quickly when wet should I go kayaking, and not suffer from odor problems with daily use. The Chaco Outcross Lace shoe met all these criteria. I wore this shoe with or without socks and never ended up with blisters nor did my feet get sweaty. The foot bed cushioned my foot so well that arch fatigue was a thing of the past. They slipped on and off easily because this model doesn't rely on a traditional lacing system. And, though I have huge (for my 5'2" height) size 9 feet, these shoes didn't exaggerate the silhouette of my feet.
Now that I'm back in New York, I continue to wear these shoes. In fact, there're comfortably on my feet now as we speak.