Note that custom orthotics only fit in certain shoes, like sneakers, where you can remove the foot bed. Also note that sneakers are not my idea of fashionable tropical vacation footwear. Yes, I'm vain. I don't want to accessorize my sundresses with my New Balance. Sue me. Rather, don't sue me, because I will be spending all of my money looking for the "perfect" tropical vacation footwear.
The last time we went on a long trip to Hawaii where I knew that I would be walking a lot, I kind of ignored the needs of my feet. I traipsed all over Waikiki in a pair of Havianas flip flops. And I almost broke my left foot. Literally. One more day of doing miles in my flip flops, and my post vacation home time would have found me in an air cast, healing a stress fracture or two. Nice. I can not afford to be that stupid again.
So, I'm trying a different approach: a Merrell sandal that is a teensy bit supportive (hence, kind of fugly). In photos, it looks a little heinous. See...

I tried one on in the store, though, and it wasn't so bad looking. The reviews on Zappos are good. I'm giving it a shot. I'm also trying a pair of Skechers as my "evening wear" walking shoe. I think I might be able to squeeze my Powerstep inserts into these babies if necessary. Woohoo, sexy!

I have issues.
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