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 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 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. 

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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.
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 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.


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.
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. 

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

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 

Leather sandals or easy flip flops> for sultry summer days? You got it. Pumps for important lunch meetings and happy hour with friends? You can count on us. And don’t think we’ve forgotten about comfort. Our shoes are beautifully designed and comfy enough to wear all day (no blisters here!) Say goodbye to sad feet and hello to a look that rocks—from the boardroom to the weekend and everything in between. Shop our different colors and styles of boots, flip flops, slide sandals, ankle boots, and more! 

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!
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.
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