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.
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.

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)!
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.
Whether you’re in search of practical mary-jane sneakers to look polished while on the job, or a pair of lightweight clogs with shock-absorbing cushioning for a day on your feet, Amazon.com offers a wide variety of women’s work footwear in a selection of styles, shapes, colors, materials, closures, and brands so you can complete your tasks in comfort.
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 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 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.

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!
Being a petite lady, I’m a size five in women’s, which proves difficult sometimes. Some shoes don’t even go down to a five! Always a six, never a five. So I’ve started resorting to buying kid’s shoes! A women’s five is around a kid’s 3-3.5, depending on the shoe. I’ve found lots of cute slip on shoes this way, for example! I always get a small internal swell of resourceful pride when I get complimented on them, knowing, little do they know, I got them for cheap from the children’s section!
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.
Ahh, shoe shopping! The perfect pair is the cherry on top of a well put-together outfit. There’s no better feeling than finding that perfect pair that goes with everything in your closet. And at J.Crew Factory, you can shop the look you need at prices you’ll love. Our shoes come in an array of classic styles and stunning colors, which means you get everything you need and nothing you don't. Colorful flats in tons of styles that easily match all your favorite outfits? Done. Whether you are looking for boots, t-strap sandals, slip-on sneakers, ankle boots, or ballet flats, J. Crew Factory has something for you.
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’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.
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.
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 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.
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