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.
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’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.
You are eligible for a full refund if no ShippingPass-eligible orders have been placed. You cannot receive a refund if you have placed a ShippingPass-eligible order. In this case, the Customer Care team will remove your account from auto-renewal to ensure you are not charged for an additional year and you can continue to use the subscription until the end of your subscription term.
Right now I’m wearing Audrey Brooke ballet flats that I found at DSW and liked so much I got them in both black and beige: https://www.dsw.com/en/us/product/audrey-brooke-winny-ballet-flat/346590?cm_mmc=CSE-_-GPS-_-G_Shopping_Flats-_-New_Flats&cadevice=c&gclid=CjwKCAiA24PVBRBvEiwAyBxf-YsFHhzrUN7TieTobdfNN7iEDu3NDesJZ8uQvBpgDPTQFkIHUFyfrBoCevoQAvD_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.

The Men's Shoes Department at Amazon.com is the gateway to the latest trends and fashions found in men's shoes today. Looking for a good work shoe that can also transition to the weekend? We've got them. See a shoe, but not sure who makes it? Check out Shoe Shape guide and discover what you're looking for. Whether it's your first dress shoe or the latest pair of casual shoes, we have the men's shoes you need for any occasion.
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 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 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.
×