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 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 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!

If you’re in need of a specialized design as well as specific construction, our shoe shape filter helps you browse women’s work footwear in shapes like heeled sandal, pump, athletic, dress boot, flat, slide flat, and work boot. Our search-by-color filter lets you pick from hues like olive green, classic black, playful floral patterns, deep browns and reds, and more. Whether you prefer a marbled leather outer with antimicrobial lining or high-quality suede with cushioned inserts, you can find a range of materials and features all right here. Plus, using our handy filters, you can hone in on quality women’s work footwear brands, including Skechers, KEEN, Timberland, and more.

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!
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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