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.
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!
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. 

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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.
Last month I caved and ordered the Siena flats by Crocs (!!) and I love them! I’m a reporter, and I’ve just started a new job at a business publication that has an in-house fashion/lifestyle magazine. Most of my work clothes previously have been traveler/hiker rugged, so I needed a pair of black flats ASAP to fit into the downtown offices I’m suddenly in. They do not look like the Crocs mules AT ALL, and I am so happy with them already! https://www.amazon.com/gp/product/B0105TPPNM/ref=oh_aui_detailpage_o00_s00?ie=UTF8&psc=1
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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 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.
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