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 work at a business school and rarely wear heels anymore. I have embraced a feminine menswear style. I have the everlane loafers, cole haan oxfords (they come in wide which translates to less narrow), an old pair of jcrew monkstrap type shoes. I have one pair of 1” -ish heels, again “wide” cole haans. Non work I do clogs/clog boots (everyone has their fancy faves but Dansko is still my go to for their sole) and multiple Ecco leather sneakers. Very comfy, those!

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
after a long search I settled on these. Not super exciting but we will see how it goes. At least they will go with pretty much everything. Sorry for the dansko rant, I am just bitter about them because they are so heavy and I wore them for so long working full time and they changed the structure of my feet! My little toe started rotating. And all the ankle rolls… hard working nurse ain’t got time for that.
Check out our latest arrivals section for the latest styles and brands in men's shoes, like Allen Edmonds, Kenneth Cole, Timberland, Steve Madden, Frye, Cole Haan, Calvin Klein, and Bass. We feature categories of men's shoes that fit the latest trends and styles, from fashion sneakers to dress boots, so you can always be on the cutting edge of men's shoe fashion.
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 think I need the Everlane heels now … I work in a corporate legal department in Northern California, but I am often meeting with executives, so I am trying to look halfways professional. I am also a 6 footer, so don’t really need heels. I love Paul Green oxfords (available on Zappos), they look great with slacks or jeans; they look essentially like mens’ oxfords (wingtip and such), but a bit cuter, and they are incredibly comfy and long-lasting.
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Emily, thanks for this comment! I work in disaster relief, so I wear work boots when I’m on sites. I LOVE that my “work uniform” is a)whatever I want when I’m remote, and b)work boots and a hard hat when I’m on site. I wear Vasque hiking boots. These are sturdy and comfortable, with traction and support. They are not, however, steel-toed or puncture-proof, which would technically be best practice. I love them and am willing to forego the latter precautions, but I know that as another commentor mentioned, Red Wing has those things. I would recommend checking out Sierra Trading Post for certain boots, because nice quality brands tend to get very expensive, but they are worth seeking out at a discount.
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 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. 

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.
Want something between a men's shoe and a boot? Check out a Chukka. Perfect for going from work to a night out with friends. For a classic comeback, the boat shoe is making waves again, making these men's shoes perfect for casual wear. Whether you lace up, slip-on or buckle down, the men's shoes department has the styles and brands you need at the prices you want.
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
Check out our latest arrivals section for the latest styles and brands in men's shoes, like Allen Edmonds, Kenneth Cole, Timberland, Steve Madden, Frye, Cole Haan, Calvin Klein, and Bass. We feature categories of men's shoes that fit the latest trends and styles, from fashion sneakers to dress boots, so you can always be on the cutting edge of men's shoe fashion.
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