Yikes! I’m leaving for Chile on Thursday. Activities will include hiking and desert excursions. But we will also be in the city, and plan to visit wineries.

My plan was to bring hiking boots, sneakers and birkenstocks. The latter are silver and I can wear them with a dress in the evening.

However, the weather report is showing lower temps than we expect, especially in Santiago. 70’s-80’s during the day. Probably 60’s and low 70’s during the evening. I’m not sure the Birkenstocks are the rught choice anymore. I would have subbed in black ballet flats, but I just passed on some that were falling apart. I have midnight blue metallic flats, but they are harder to pair with things. They also have no support, and I’d be concerned about them in the rain (supple leather).

My feet are fussy and we walk a LOT. I also need the option to change out shoes at night and from day to day. The only shoes I’d be happy with in this third place are my Teva boots and my Birkenstocks really, comfort wise. But the weather won’t be quite right for either.

Should I suck it up and bring the Birkenstocks, even if I’m a little cold at night? Or find some sturdy black flats that will look okay with a dress ASAP? Bring the Teva booties and just use them at night or on rainy days (they are waterproof but don’t look it)?

PS- hope to bring this dress because I can also use it as a tunic over jeans. I’d wear my metallic Ecco sneakers that case, but it would be nice to have a third shoe, and to be able to wear this with or without tights.

ETA: trying to pack carry on, as that is my personal strong preference. More than 3 shoes isn’t possible. This will be more of a gear trip than a dressy trip. I just want ONE decently drrsssy option because I often need a change of shoe at night, and want the option to go to a nice restaurant at least once in Santiago. I’ve decided against heels entirely.