I absolutely LOVE Pikolinos! They are definitely the most comfortable and longest lasting/wearing shoes I’ve owned. I have 2 pairs of sandals that are going on 4 and 5 years of daily use from May – September for work, city walks, and travel. Last fall I purchased a pair of Pikolino brogues and loafers that were comfortable right out of the box, and are perfect for work or a dressing up a casual outfit. Unfortunately, I find the shoes to be extremely expensive in Toronto, but I’ve been fortunate to come across the brand during visits to Portugal, France, and Spain where they are much more reasonably priced. 

I have such a hard time with content like this because I work a (literal) blue collar job. my go to work shoes are 5.11 ATAC 8″ boots. theyre kind of expensive, but theyre by far the most comfortable tactical boots I’ve ever tried on. I am in the market for a new pair though, and I think I want ones with a puncture resistant shank, so if any other work boot wearing cup of jo readers have recommendations Id love to hear them.
I commute in Cole Haan ballet flats (unless boots are needed) and then change into heels at my desk. My most comfortable are the Sam Edelman Hazel pumps, which are honestly the most comfortable heels I’ve ever worn. Pro tip – Zappos sells the black and nude (in various materials) in a narrow width, which has been a life saver for my feet! I’ve also found Ann Taylor and Tory Burch heels to be pretty comfortable and narrow feet friendly.
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.
I can’t say enough about Rothy’s flats! I have two pairs – a leopard print and a bright blue with orange soles and they are both the pointed toe flats. I get a ton of compliments from random people on the street, and all of my coworkers have bought a pair. They feel like sneakers but are fashionable and can be washed in the washing machine so if I get caught in a rainstorm, they aren’t ruined.
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!
Taos ballet flats. They had some in pewter a few years ago, with a laser cut design along the opening, that I wore daily until the leather on the right toe of one of them cracked. It was the only time I’ve ever felt heartbroken about shoes. I now have a pair of shiny patent leather (black) Taos ballet flats, but they lack the laser cut detail. I would pay double for another pair of those original flats. So cute, comfortable, and perfect with pants or dresses, even for someone with narrow feet. 

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)!
When I was in my early 20’s, I realized that I would not be able to sit at a desk for the next 40 plus years and went back to school to get a degree in occupational therapy. I specialize in pediatrics and work in a sensory integration gym with mats on most of the surfaces, so we take off our shoes when we treat. I wear Crocs at work! I play with children all day long and I don’t have to wear women’s shoes, ever, which I find impossible to walk in, anyway. When I go out I wear Frye boots in the winter or Mephisto sandals in the summer. I refuse to hobble myself.
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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 second Ali’s comment! Have you tried Gekk’s? I’m newly obsessed with them! They’re no show socks except you basically glue them in place in your shoe so they don’t slide around like normal no-show socks seem to do constantly. Then if they get stinky you can pull them out and wash them. They’re not cheap but neither is replacing smelly shoes every three months :-)
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)!
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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.
When I was in my early 20’s, I realized that I would not be able to sit at a desk for the next 40 plus years and went back to school to get a degree in occupational therapy. I specialize in pediatrics and work in a sensory integration gym with mats on most of the surfaces, so we take off our shoes when we treat. I wear Crocs at work! I play with children all day long and I don’t have to wear women’s shoes, ever, which I find impossible to walk in, anyway. When I go out I wear Frye boots in the winter or Mephisto sandals in the summer. I refuse to hobble myself.
I can’t say enough about Rothy’s flats! I have two pairs – a leopard print and a bright blue with orange soles and they are both the pointed toe flats. I get a ton of compliments from random people on the street, and all of my coworkers have bought a pair. They feel like sneakers but are fashionable and can be washed in the washing machine so if I get caught in a rainstorm, they aren’t ruined.
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’m a long-time reader but first-time commenter – this post has made me want to share my shoe shopping secret. On New Year’s Day, Saks has an incredible sale (up to 75 percent off!) before noon. It’s amazing for shoes! In the past few years, I’ve gotten black Rag and Bone 1.5” heel booties and grey suede Stuart Weitzman loafers for 70 percent off. Still a splurge, but so worth it. I wear them constantly. I work in a formal environment and have to be *dressed* for work each day (though I avoid suits). I also generally avoid heels, save for a pair of ridiculously comfortable oxford heels I got from L.L.Bean, of all places, and always get compliments on. Flats, loafers, and boots are my mainstays, even though I’m short and pretty small. You don’t have to wear heels to look professional!
You can even find wallet-friendly women’s work footwear when you search by our price and discount filters. Our shoe width and size filters can help you find the right fit, and if you need a new pair quickly, you can take advantage of our free shipping on eligible items. Better yet, if you find they don’t quite fit your needs, you can take advantage of our free returns on eligible items.

When I was working full time, on my feet all day, I had an amazing pair of Naturalizer boots, so I’d recommend that brand for sure, Also a favorite, Geox shoes are incredibly comfortable. I still wear a pair of wedge sandals I bought about 5 years ago, and they feel like you’re walking on pillows! Bought them in brown too, love them so much! Geox has seasonal warehouse sales, where you can score some great deals, and they have mens, ladies, and childrens footwear.
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.
Love this post. I used to always buy cheap shoes and they would leave me tired and blistered every time. One Christmas I got the Everlane Babo shoes and I am NEVER going back. I literally where these shoes everywhere—work, out, walks around the city. They are by far the most comfortable shoes that I’ve ever owned. I feel so passionately about these shoes that I will find myself on unsoliciated ramblings on elevators telling everyone they should buy these shoes. I realize they aren’t the *cutest* shoe (I call them my elf/witch shoes) but I love their interesting shape and they go with everything! Do yourself a favor and buy these shoes: https://www.everlane.com/products/womens-modern-babo-black?utm_medium=cpc&utm_source=pla-google&utm_campaign=838132553&utm_content=197323891655&utm_term=pla-341116225674&adgroup=43249559952&pid=2414-8509&device=m&gclid=CjwKCAiA24PVBRBvEiwAyBxf-TmH1XO5IYJ8Bi3MK5k-SUMQmo8tvfiC1Gc0v86JuwjptnbHnglemhoCwPAQAvD_BwE
I absolutely LOVE Pikolinos! They are definitely the most comfortable and longest lasting/wearing shoes I’ve owned. I have 2 pairs of sandals that are going on 4 and 5 years of daily use from May – September for work, city walks, and travel. Last fall I purchased a pair of Pikolino brogues and loafers that were comfortable right out of the box, and are perfect for work or a dressing up a casual outfit. Unfortunately, I find the shoes to be extremely expensive in Toronto, but I’ve been fortunate to come across the brand during visits to Portugal, France, and Spain where they are much more reasonably priced.
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.

So I tried the Susina loafers and they ARE soft as butter, which was nice, but I know I am hard on shoes, so I returned and opted for the Everlane Modern Loafer (and got my official Everlane Club Member card…jk) Significant price difference, but I feel worth it. LOVING them! Ordered 1/2 size up and will likely use a stretcher to break in the toebed a bit more.
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.
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