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I have a pair similar to these. I have worn them all over Europe - walking all day. They are waterproof so keep you nice and dry.
https://www.zappos.com/p/cole-haan-american-classics-plain-toe-boot-waterproof-black-black-waterproof/product/9806844/color/316545 |
| Clogs! I'm telling you - clogs. |
| Bass Weejuns |
| I also love my Blundstones. They are my fall/winter walking shoe. Great in all weather. |
Not a huge fan of the loafers, but I like Vionic flats. |
| My comfiest shoes and boots include: Blundstones, Doc Martens, Fit Flops, and Birkenstocks. I have some Taos sneakers that I like, and might try their shoes to see if they work for me as well. |
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Girl, I just bought some Naturalizer loafers. They were 1/3 of the price of the fancy brand the saleswoman at Nordstrom tried to sell me and look exactly the same.
Also, Sorel shoes are very stylish nowadays and so comfy. |
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These Vionic heels are very comfortable! Not great for winter, though: https://www.vionicshoes.com/chardonnay-heeled-sandal.html?color=722
I have some Vionic loafers (not the ones mentioned already, I think mine are the Sellah style) that are all black and very comfortable. |
I have had luck with black waterproof wide width modest heel ankle boots from Naturalizer and Rockport. When I find shoes or boots that fit well, I buy multiples. Eastland might work. They just discontinued the rubber bottomed penny loafer that was my favorite casual shoe for 25 years. They have some wide widths. Canadian boot brands look good to me - just never been in the right place at right time to end up with them. But they do know winterwear! |
| Where's an in person store to try on a lot of these suggestions? |
| I prefer to walk into DSW, Nordstrom or Macys to try on shoes. I know you think you don’t have the time for this, but purchasing, waiting for shipping and returning is time consuming too. |
OP here. This actually IS what I do. Buying shoes online, unless I already know exactly what I want, rarely works for me. Hell, even if I’m reordering a shoe I already own, I find the second pair rarely fits the same (I’m looking at you Birkenstock.) |
| I have black suede birkenstock mules that I wear for these types of occasions |
OP here. This has actually been on my list to try because Birks are my go to summer shoe. Do you have Boston, Berkeley or Zermatt? |