The 11 Most Comfortable Dress Shoes for Women, Tested and Reviewed

We recommend these shoes for nearly any setting (we wore them everywhere from art fairs to running errands, on all types of ground). The shoes have a .75-inch flat heel with medium and wide size offerings. We concluded the shoes are plenty comfortable due to the solid amount of cushion given in the insole. Luckily, if you’re walking a lot, the shoes will likely not rub, chafe, or pinch your foot. The top of the heel is a bit stiff when you first wear them, which means they require a slight break-in period. And if you’re looking for high-arch support, then this is probably not the shoe for you, but you can always add your own insoles. 

To add to the pro column, our feet were much less sweaty in these shoes than others and didn’t create that sticky feeling (which sometimes comes with cushion insoles). The style fits true to size and can be dressed up or down thanks to the chic gold-toned design on the top of the flats. 

The Details: 5 to 13 | Synthetic, faux leather, microfiber, faux suede

These Starling flats are the perfect mix of chic and comfortable. You can shop them in velvet, leather, or suede and in many colorways, spanning from black velvet to a classic taupe leather, making them inherently unique for any occasion. We love the quilted and silky cushioned insoles (that are made up of seven layers for the ultimate cloud-like feeling) that are reminiscent of wearing soft slippers around the house. 

They’re perfect for office days and are easy to slip on when you’re on the go. We avoided wearing the velvet pair when the weather was damp due to a fear of ruining the fabric. If you’re looking for an all-purpose shoe, then the traditional black leather option may be more up your alley. The flats can be worn with virtually anything — from slacks and skinny jeans to skirts and dresses.

The Details: 5 to 12 | Velvet, rubber, grosgrain

Firstly, these shoes are adorable, and the contrasted colors and trim to the main shade of the shoe are a testament to that. They have a 1.77-inch round-toe block heel that makes them perfect for the office or any other casual occasion (it also makes them more stable than skinny heels). We wore these for more than seven hours at a time and felt the arch support, heel rebound, and forefoot support throughout the day. There’s even a secondary heel patch for additional comfort. 

We received a few blisters from the shoes upon first wear due to the chafing of the fabric on the sides and back of the heel. However, after a few break-ins, our feet did not get irritated. Overall, we’d still say these are more comfortable than an average heel. They are also ideal for rain conditions, and we never felt like we were going to slip on a wet sidewalk. 

The Details: 5 to 11 | PU foam, rubber

These pumps are made with triple-dyed Italian suede, which means they instantly look stunning and feel high-quality. The heels have indented insole support at the heel and the arch of the shoe —  a feature lacking in luxury pumps — making them comfortable right when you slip them on (they even have several millimeters of extra footbed padding). The 3.3-inch stiletto heel is not too tall and you can’t walk around securely in them; however, the pointed-toe design may pinch your toes during the first few wears. 

We loved that these shoes are breathable, as we never experienced our feet overheating or sweating profusely while walking in them. The shoes may need to be worn around the house first to be broken into before taking them out on a date night. There are so many versatile textiles and colors to choose from, should you want to go bold or classic.

The Details: 4 to 13 | Suede, leather, rubber

Right off the bat, the style of these Clarks Mary Jane shoes stood out to us. The top two skinny straps can be adjusted, which is helpful since the toe box has a lot of room. Available in black patent or silver leather, these block heels feature a contour cushion footbed to provide increased arch support (especially in the ball of the foot and the heel, which can certainly be pain points for many after long periods of use). The footbed even has tiny holes in it to encourage breathability. 

These shoes have a leather lining and rounded toe shape that may make it feel like you’re wearing sneakers, considering how sturdy they are thanks to the rounded heel. If you have wider set feet, these may not be the best fit for you. We wore them around the city, the office, and even to an outdoor wedding, so we know for a fact that these Mary Janes are extremely functional. These would be a great shoe to pack and wear with jeans or a dress while traveling.

The Details: 5 to 11 | Leather, rubber

We think these Intentionally Blank London Mary Jane shoes, available in three colorways, are ideal for evening events or the office. After wearing them for long periods, we noticed how supportive they are. The dress shoe has a wider shaft and a memory foam footbed for ultimate comfort, along with a leather upper and lining. We also love how chic the top bow is — you can wear them with dressier clothing or jeans to dress up your wardrobe.

Note that there will likely be a necessary break-in period for these leather shoes due to the stiffness of the material, so wear them around the house or short distances first so that your feet get used to them. They are advertised to be better for wider feet while also featuring a hidden elastic strap. The heel is just over 1 inch, so they will give you a little height boost, but not enough to make them uncomfortable. 

The Details: 35 to 42 | Leather, grosgrain, memory foam

If you’re looking for a stylish flat that you’ll get a lot of use out of, then this is it. We love the contrast between the shiny top part of the shoe and the regular leather (you can even see the shine in the black on black offering). The Camelia slingbacks have an adjustable ankle strap that allows them to fit perfectly — a welcome feature as the fit of pointy shoes can usually be a toss-up. 

The buckle is gold-toned, while the rest of the shoe is handcrafted from Italian leather and features a natural rubber sole. You can sport them out on the town during any season (we prefer wearing flats in the fall, spring, and winter when it’s not incredibly hot out). We found the shoe is ideal for long wear — as good as 12 hours — and we didn’t experience any blisters or redness. 

The Details: 5 to 12 | Patent leather, calf leather, natural rubber

These knee-high boots, available in suede or leather, are offered in both medium and wide sizing. We wore the leather version for long periods of time and loved how comfortable they were for all-day wear. The flared heel is just over 2 inches, which makes them fashionable but not intolerable or painful. The boots have contour and comfort technology, and we were happy about the softness of the leather shaft when walking miles at a time. Consider using a leather protector spray if you plan to wear the shoes in the rain, as these aren’t waterproof. 

Although slightly on the pricier end, these boots are very high-quality and have a side zipper closure to slip on and off easily. Due to the fact that the fashion shoe is made of real leather, they will not be as breathable as some of the aforementioned shoes. However, our feet did not overheat as much as you’d think. After being worn dozens (if not over a hundred) times, the leather received some scuffs but is still considered to be in great condition. 

The Details: 5 to 12 | Leather, suede, recycled polyester

We adore the City Dry technology that this leather bootie features. The boots are made of waterproof Italian leather that won’t get ruined by rain in the slightest. You’d never guess that there is a microfiber lining in these booties that is similar to the feeling of fleece. You could even wear them without socks and they’d still be comfortable. Despite the 3-inch heel, we felt that the boots were more cozy than other 1-inch boots we’ve tried out. 

Although it’s a basic black boot, they look incredibly fancy and are versatile for any setting. A pro tip for any leather shoe is to first wear them with thicker socks and use a shoe stretcher spray inside. The sole was extremely cushy so you can walk long distances with them, making the shoe a go-to bootie no matter the time of year. They’re available in colorways black or wine. 

The Details: 5 to 12 | Leather, microfiber, rubber