These Surprisingly Comfy Dress Shoes Will Feel Like Walking on Clouds

These Surprisingly Comfy Dress Shoes Will Feel Like Walking on Clouds (1)

Graphic by Giovanna Chung/KCM

Including styles Katie wears.

Taking off uncomfortable shoes after a long day at work is one of the most freeing feelings in the world. But what if you didn’t spend your 9 to 5 wishing you could kick them off mid-meeting? In our opinion, comfortable dress shoes don’t have to come at the cost of fashion, especially now that the ever-changing definition of “business casual” is flexible enough to suit a wide range of shoe styles.

Whether you’re heading back into the office or want to upgrade your shoe game, adding some new kicks to your collection can seriously change the way an outfit looks, even if you’re just wearing jeans and a T-shirt. Many of our favorite brands offer cushy heels and flats that are both dressy and on-trend, so there’s no need to torture your feet for the sake of style. Some of these make more of a statement than others, but all of them are comfortable enough to wear throughout an eight-hour workday, even if you find yourself on your feet instead of sitting at a desk. And since Katie knows a thing or two about creating a wardrobe that marries comfort and structure, we included some of her suggestions.

From beautiful pumps that take you from the office to happy hour to comfy loafers you can wear to Sunday brunch, here are 11 pairs of dressier shoes that won’t leave your dogs barking.

The Most Comfortable Dress Shoes for Women

Steve Madden Lotto Loafer

Zappos

If you’ve been on the hunt for a pair of loafers that’s nearly identical to the pair Katie has been wearing, this is the one. A chunky lug sole will give you some height, but they aren’t extremely heavy or clunky to walk in. Reviewers say they also have great arch support, which is perfect for those who spend long days on their feet.

$90 at Zappos

Allbirds Tree Breezers

Allbirds

Commuters rejoice — these flats are comfortable enough to walk miles in without looking like an orthopedic sneaker. We already love Allbirds for their super comfy sneakers, and these flats are made from a similar material, meaning they’re washable and breathable. 

$100 at Allbirds

Ma’am Ruth Mules

Ma’am

Katie loves Ma’am’s sandals, and these heeled mules are no exception. A pointed toe elongates the look (without crushing your toes), and the strap near the top adds a cute touch while also keeping your foot from sliding out of the shoe while you walk. These come in five different colors, including a tan croc style, making it hard to choose a favorite.

$150 at Ma’am

Nisolo Emma d’Orsay Oxford

Nisolo

For the comfort of an Oxford without the heavy feeling, try a d’Orsay shoe instead. These have a fun cutout on the side that keeps your feet from getting hot and sweaty during a full day of work, but they maintain a formality that won’t look out of place when meeting with top executives (or being one). The leather is buttery soft and comes in four different colors, so they can slide into any wardrobe seamlessly.  

$99 at Nisolo

Everlane Day Heel

Everlane

Fact: Donning heels all day can be a literal pain. Also fact: This pair by Everlane flips that script. With a reasonable and supportive block heel and a stretchy back that moves with you, you’ll find yourself reaching for these every day.

$175 at Everlane

Birdies The Swan

Birdies

If the skin at your heels has a tendency to tear with stuctured shoes, try a pair of elevated mules. This versatile braided style will be a springtime go-to, whether you’re on the clock or packing them for your next vacation. Birdies also takes a thoughtful approach to footwear design, ensuring every style they make is as comfortable as possible. This pair has a seven-layer footbed that has a soft squish with every step, and the interior is lined with mesh so the fabric doesn’t rub uncomfortably against your foot.

$145 at Birdies

Clarks Amberlyn Ruby Sandal

DSW

You can definitely wear sandals to the office, especially when they’re as sleek as these. A chunky heel makes them easy (and comfortable) to walk in, and they even have a cushy sole to cradle your feet all day long. They’re dressy enough for weddings and cocktail hours, too, but they can easily be worn for casual outings. 

$70 at DSW

Vionic Kensley Loafers

Zappos

Dress shoes don’t always have to be black or brown. In fact, we believe metallic is fair game for a day at your desk. A lug sole and patent leather offer a modern twist on the classic loafer, and they feel like something Diane Keaton would wear. Win-win.

$130 at Zappos

Dolce Vita Reyes Mary Jane

Nordstrom

Balletcore is still trending, but we’re not mad about that. These delicate pink flats have a square toe that adds a more contemporary and grown-up slant to them, so you won’t feel like a toddler straight out of dance class. It also features a delicate strap with silver hardware that adds a bit of security for when you’re power walking home after burning the midnight oil.

$120 at Nordstrom

Maguire Lorca Leather Knee-High Boots

Maguire

Consider these a luxe version of a go-go boot. Maguire’s Lorca knee-highs come in three different colors and three calf widths, making them great for those who usually struggle with too-tight boot shafts. We’d pair these over jeans for colder months, but once things heat up, they’ll look amazing with mini skirts and dresses, too.

$340 at Maguire

Aerosoles Lilia Loafer

Aerosoles

A classic leather loafer, but with a (literal) twist! This Aerosoles shoe has a thick sole that adds height without requiring high heels, which is why Katie loves this trend. Reviewers say this style runs a little big, though, so consider sizing down a half size if you want a snug fit. 

$55 at Aerosoles

Madewell Idris Ankle Boot

Madewell

Leather booties are wardrobe warriors that can be worn in and out of the office. This pair from Madewell leans western without feeling costume-y, and the heel is nice and chunky, so you won’t feel like you’re teetering on a tightrope with each step you take.

$178 at Madewell

Sam Edelman Tarra Slingback Pump

Nordstrom

We never thought we’d say this, but a little toe cleavage can be sexy. Otherwise a classic slingback heel, this pair has a tiny cutout that shows a little skin. A similar cap-toe heel was originally made famous by Chanel, but this version offers a more accessible price point.

$77+ at Nordstrom