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I bought a pair of Ecco sandals (the hauraches) for my summer Italy trip, and they were the best! They look kind of dowdy online, but are way cuter on than in the photos, and they have a really supportive insole, and really stable almost sneaker like outsole/bottom, so they really hold up for tons of city walking, while keeping your feet cooler than a regular sneaker, and work with dresses and pants.
I’ve been wearing Sam Edelman Felicia flats to work almost everyday for over a decade (not the same pair…I have a couple pairs at a time that get replaced every two years or so). They are cute and have a padded sole so they’re comfortable to walk distances in. A few years ago the manufacturer changed the design a bit, so now they have an embroidered logo on the heel (yuck) and are slightly less comfortable for my foot. I haven’t found anything as good yet to replace them though, so I am soldiering on with them.
I work for a public transit system, so I have a job that has my time split in offices with public officials wearing suits and walking around in train yards and tunnels with oil-covered rail mechanics. Sometimes I’ll have time to swap out my shoes at my desk, but I’ve relied on these suede Vans https://goo.gl/yVJZxT for 3 years now. They’ll never pass for heels, but they are incredibly versatile and comfortable plus the price point is perfect.
For those of us not in an office setting that requires heels and the like…Hoka One One Bondi 5 and Hoka One One Clifton 4 running shoes are amazing. Working in a research lab on my feet all day I’ve found there’s no point in wearing anything other than sneakers (and absolutely no open toed shoes – you’ll lose a foot!). I have gigantic and WIDE hoofs with a supination issue and high arches. Hoka One One makes the best shoes for my feet (the Bondi is the cushiest). Insoles that support your unique foot shape are a must (I’ve found that Superfeet Green insoles do it for me, plus a custom pair of orthotics for long runs). But seriously, go see a podiatrist and get your feet and your gait analyzed (multiple times throughout your life – it changes!). Well worth the co-pay.