Look (and Feel) Good: Your Guide to the Most Comfortable Women’s Dress Shoes

The Most Comfortable Women's Dress Shoes
Disclosure: This post may contain affiliate links, meaning we get a commission if you decide to make a purchase through our links, at no cost to you. Please read our Disclosure for more info.

Sarah Jessica Parker famously told Net-a-Porter in 2013 that her feet were permanently damaged from wearing high heels on the set of “Sex and the City.”

And while the moral of the story is that you probably shouldn’t be wearing sky-high heels every day, it doesn’t mean you have to sacrifice comfort for glam.

In this blog post, we’ll talk about some of the most comfortable women’s dress shoes you should have in your closet.

Read on for more information.

The Flat

The flat is the holy grail of comfortable women’s shoes. They fit any occasion, whether you’re in a business formal setting, at a black-tie event or are simply wearing a nice summer dress and flats.

But, not all flats are created equally. In order to make sure the flats are comfortable, you need to forego the cute cheap ones you might find at fast fashion stores and invest in a good pair.

Of course, if you’re only planning on wearing the fast fashion branded shoes every once in a while, you’re in the clear. But if you have a job standing up all day, you may want to nix them and go with something a bit more sturdy.

Go with a pair of shoes made of real leather or well treated vegan leather. Make sure you have at least somewhat of an arch support in the shoe.

If you have trouble keeping shoes on your feet because they’re too narrow, try wearing an orthotic insert or buying a shoe with elastic or a buckle.

DREAM PAIRS Women's Revona Silver Glitter Low Wedge Ankle Strap Flats Shoes - 8.5 B(M) US

The Wedge

The wedge is a perfect shoe to elevate any outfit, whether it be for business or a casual look.

A wedge with an espadrille is even better, as this can make your look more summer-y or spring-like.

The wedge works well with a dress or a nice pair of pants, either trousers or dark wash jeans, for a formal event.

Wedges also pair well with casual outfits, dressing up a summer dress or a t-shirt and shorts. Check out this website for some ideas of how to pair a casual t-shirt with a pair of pants for the ultimate care-free ensemble. Add a wedge, and you’re ready to rock a laid-back but glam look.

Dr. Scholl'sHarlow Taupe 8.5

Platform Shoes

No, they’re not just shoes you wear to the disco. You can wear platform shoes with any formal outfit to add both a little pizazz and a little bit of height.

While some people can think a platform shoe is incredibly uncomfortable, it actually can be more comfortable than a regular heel. This is because a platform shoe adds height in the front and the back, and doesn’t necessarily force your foot into an unnatural position.

In fact, men used to wear platform shoes back in the day to add a little bit of style to their own outfits. And if men could wear them, you definitely can too.

For a little bit of added comfort, try putting a gel insert in the shoe where the balls of the feet go.

CL by Chinese Laundry Women's Go On Platform Dress Sandal, Nude Super Suede, 7 M US

Low Chunky Heels

Want to add a little bit of height, but don’t want to add a stiletto to your look? Try a conservative low chunky heel. These shoes are often preferred by older women, as they allow you to add a touch of class without having to sacrifice the ability to walk.

But, that doesn’t mean you have to a member of the AARP to rock them. Stores sell low chunky heels in a variety of designs and colors, and you definitely find a set that matches what you’re going for. You’ll look chic and your feet won’t be screaming in pain at the end of the day.

DREAM PAIRS Women's SDPU2230W Edena Chunky Closed Toe Low Block Heels Work Pumps Comfortable Round Toe Dress Wedding Shoes, Size 8, Black

Higher Chunky Heels

If you want something a little more youthful, try a pair of higher chunky heels. These give off a younger vibe, but also offer a greater deal of support that a thin heel.

A chunky heel is also fantastic if you have to work somewhere where there is a lot of grass, or you’re attending an outdoor event. There’s nothing worse than having your stiletto heels sink into the ground, and with a chunky heel, you can be sure that doesn’t happen.

DREAM PAIRS Women's Black Heel Pump Sandals,SDHS2205W

A Dress Boot

If you’re looking for a comfortable way to stay stylish, try a dress boot. A low bootie or a knee-high can both be a perfect way to express yourself. You can pair either with a nice dress pant or a skirt. Either way, you’ll be sure to stay professional and looking on point.

A dress boot is extremely versatile, in that it comes in all shapes and sizes and colors. For a formal occasion, you can get away with a glittery boot or a nice leather one with fine detailing and hardware.

A good dress boot can be of any heel height, making them as comfortable as you need them to be.

DREAM PAIRS Women's Stomp Black High Heel Ankle Bootie Size 11 B(M) US

Purchasing the Most Comfortable Women’s Dress Shoes

The most comfortable women’s dress shoes are highly subjective. What a friend may find to be as comfortable as slippers, you may not find as such. This is because everyone has different feet, posture and structure of their body.

Be sure you try on any pair of dress shoes you want to last you several hours throughout the day. This way, you’ll know if they fit the bill or not. You can also put in pads or orthotics to help them fit more snugly, or help them be a little bit more comfortable.

Struggling to put together your shoe collection? Click here for the three shoes every woman should have in her closet.

Scroll to Top