I have the same problem with some of my shoes, you just have to pick the right store. I like nine west and MK but I have bought a few online I love and are comfortable. I have found a site I like called http://www.heelstoday.com, I bought a 6in stiletto from them that turned out to be great and I have bought two other pairs. So I would look at them if you are in to online shoes.
My husband splurged and got me a pair of Tory Birch flats for Christmas this year (these: https://www.toryburch.com/minnie-travel-ballet-flat–leather/32880.html?dwvar_32880_color=232&cgid=shoes-ballet). After years of wearing el cheapo Target flats, it was AMAZING. Zero break-in period. One of the most comfortable pairs of shoes I’ve ever worn. It has definitely made me realize that, if you can float it, better quality shoes are worth it!
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. 

If you’re a commuter, I really recommend the brand All Black! I have a few of their slip-on Vans-style shoes and have received so many compliments on them. They’re super comfy for the commute into work, and they’re nice enough to wear in the office if you work somewhere a bit more casual/ slip off super easily if you’re running to a meeting and need to quickly change shoes. They’re the best (and currently on sale)!
I’m a produce manager so I need to wear comfy, heavy, non-slip shoes. After much searching, I found these https://m.6pm.com/p/shellys-london-tulle-hiker-boot-leopard/product/8940739/color/429?zhlfid=139&kpid=42196438&ef_id=WZirBgAAAHxMmQN_:20180310231403:s ( although I got mine for $60!) and they are both cute and functional. And I get compliments on them all the time.
Basically, these are them. https://www.deichmann.com/GB/en/shop/home-ladies/home-ladies-shoes/home-ladies-shoes-loafers/00009001307653/Slip*On*Casual*Shoes.prod?gclid=EAIaIQobChMI8J6yqf_f2QIV7bXtCh1wiAn0EAAYASABEgIeU_D_BwE&adword=google%2FBrand_Brand_Deichmann%2Fsearch%2Fdeichmann&imgFmt=&_=1520624405081&mlid=1178.26.244312.44044fabbd4970dcb4af7508ed681eb3…0.1520624402.1.1523216402&fromCategoryDetail=true&positionInList=46

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