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#SheWomanManHatersClub

Another vote against Toms due to lack of arch support and less than optimum cushioning. I wanted a pair because they are so cute & would be very versatile, but I nixed them after trying them on. Not nearly as comfortable as they are cute.
 
Last time I fretted about being somewhere and needing good shoes to walk a lot, I just ended up wearing flip flops and walking hours and hours and miles in them without issue (except dirty feet). I guess you wouldn't want flops in Chicago November, but I guess I just wonder if you really need specific walking shoes or just wear something moderately comfortable? Just anything you have already that doesn't give you blisters or something?
 
Oh god flip flops are the wooorst for walking long distances for me. Maybe fancier ones with super support but I don't own any like that. And walking around the city in them grosses me out. I don't have to wear fancy shoes to work and don't have to stand much so I don't have many with support or that would be suitable for walking a lot without getting tired feet. I think maybe the wool socks would help though so maybe that will make the boots a viable option!

I really think we walked like 7-10 miles last time.
 
thicker socks in your boots does seem like a good idea!

I wore cheap Target or Old Navy flip flops all throughout my trip to Rome, definitely not fancy or supportive. Washing my narsty dirty feet at the end of the day was crazy refreshing. Guess I'm lucky to be able to wear crappy shoes for lots of walking.
 
Oh man Dr. Scholls has some REALLY cute shoes! Hopefully I can find some in stores so I can try them on. Thanks for the rec!
 
Clark's can be $$$. Just forewarning. That said, they're usually really really comfy... so maybe try on the Dr. Scholls first :)
 
I did a brief check online and they appear to be having a pretty good sale right now so I'm hoping it's the same in-store!
 
I love my Danskos, Eccos and my Tsubos for walking. There are some cuter (ie not clogs/mules) Danskos if you look. But the Dr. Scholl's suggestion intrigues me for the future.
 
Another option for the boots would be to try some inserts that could take up some extra space/support/comfort. (Also boots might be a good choice in November in case there is snow or the sidewalks are wet.)
 
Fell in love with the duvet cover on the front of Better Homes & Gardens... looked it up... $675. LOL NOPE.

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