Cute Comfy Shoes

Are you struggling to find cute and comfy heeled shoes for work or a girls’ night out? Then this is the blog post for you! It’s taken me literally YEARS of sore feet, research, and shoe blogging to compile this list. I’ve personally worn these shoe brands around NYC (with photos below to prove it!) Therefore, I’ll periodically update it for you as I discover new heels to add.

Why is finding a pair of cute AND comfortable heels such a challenge? As I write this blog post, I quickly glance at my beautiful shoe closet. I wouldn’t dare wear some of my fanciest heels for a walk to the NYC subway, lol. : )

Even though I’m a podiatrist, my feminine desire to wear cute shoes occasionally trumps my desire to wear comfortable ones. However, after living in New York City for 10+ years, I’ve learned that owning comfortable heels and shoes is essential.

Sarah Flint’s designer heels’ have comfy, cushy arch support. More on these below–keep scrolling!

This post is all about cute, comfy heeled shoes to wear to work or a girls’ night out. This post also contains affiliate links, meaning I’ll receive a commission if you purchase through my link at no extra cost to you. These suggestions do not replace an examination by a licensed podiatric physician. See Terms

Here’s a list comfortable heels you can actually walk in, organized by brand. Not every shoe or brand on this list will work for you, as not all feet are the same. The goal of this list is to receive compliments on these shoes and tell your friends, “THANKS, THEY ARE COMFY TOO!”

1. Naked Feet Shoes: Comfy Heels for Going Out

This brand is called “Naked feet shoes” for a reason–feet have a natural feel in them. I own four pairs of shoes from this brand which includes the boots pictured above. All of Naked Feet Shoes’ boots, heels, and sandals are crafted with super soft leather and have plush memory foam footbeds. This shoe brand works well for average or wide sized feet. I have a small bunion and it’s wasn’t irritated during wear.

This shoe company’s style is classic and timeless–perfect for your seasonal capsule wardrobe.

CLICK HERE TO SHOP NAKED FEET SHOES ON ZAPPOS

More Naked Feet Shoe options you might like, select an image below to shop:

2. Cole Haan: Comfiest Heels for Work

Cole Haan has been my long-standing favorite shoe brand for many years. Having worked in midtown Manhattan, it’s my go-to brand for formal business wear. The company, once owned by Nike, still maintains Nike’s sneaker comfort in Cole Haan’s dress shoes. Sadly, size-wide isn’t available on some sites, but this brand still deserve a significant spot on this list!

CLICK HERE TO SHOP COLE HAAN ON NORDSTROM

Or shop shoe options below

3. Ally Shoes: Comfy Cute White Heels Designed by a Podiatrist

CLICK HERE OR IMAGES TO SHOP ALLY SHOES

Ally shoes are designed in SOHO NYC by a very inspirational group of women–including one podiatrist. They are very size inclusive, available in narrow, wide, and extra wide. When you place an order, the company sends two pairs to ensure a proper fit. The inside cushioning feels like heaven on my feet. Due to their ergonomic design, they are relatively easy to walk in. The design is unique compared to other heels I’ve previously worn. From my personal experience, these shoes have a slight break-in period. The high-quality suede/leather will take a few wears to form around your toes. Use code Drcasey for 10% off your first pair of full-price shoes.

4. TOM’s: Comfy Heels Amazon Best Seller

This brand is mainly known for its cute flats, but they also have some adorable and COMFY heels! Amazon reviewers rave about this specific pair. Why are wedges recommended over stilettos for comfort? Keep reading to find out!

CLICK HERE OR IMAGES BELOW TO SHOP TOM’S ON AMAZON

Wedges are a smarter footwear choice because:

They allow our body’s weight to be dispersed more evenly throughout our feet.
Stilettos place our body weight on the balls of our feet.
Easier to walk in than stilettos.
You won’t sink into grass or get stuck between wooden planks on a deck with a wedge!

5. Sarah Flint: Favorite Celebrity Comfy Heel for Narrow to Average Feet

CLICK HERE OR IMAGES TO SHOP SARAH FLINT

There are two reasons celebrities Amal Clooney and Alexa Chung wear this shoe. Firstly, they are SO chic. The added design details, i.e., little bows, colorful designs, soft Italian suede, and leather, all elevate the shoe line. Secondly, my feet feel good walking with anatomical arch support and soft toe-box cushioning. Allow me to explain; wearing a shoe with arch support helps ease pressure on the plantar fascia, the connective tissue on the arch of our feet. Her shoes are cute; it’s easy to forget that she designs them for comfort. Yes, Sarah Flint’s shoes are high-priced, but the quality and comfort are worth every dollar!

Block heels are a preferred footwear choice because:

They are more supportive than a stiletto on our feet.
Still offer added height.
You’ll be less likely to get your shoe caught in a street grate or between a sidewalk.
They are easier to walk in.

{RELATED POST: A Complete Guide to Foot Massage at Home}

6. Walking Cradles: Size Inclusive Comfy Cute Brand on Amazon

CLICK HERE OR IMAGES TO SHOP WALKING CRADLES ON AMAZON

Walking Cradles brand is a very versatile comfort shoe brand. Not only do they have an incredible variety of shoes, but their brand is also one of the best on the market for size inclusivity. Their shoes are available in narrow, regular, wide, and extra wide. The red patent heels in the photo are my go-to holiday party heels. I paired them with my Gucci Dionysus bag and knit white sweater. Aren’t they SO cute?

7. Vionic: Best Heel Brand for Everyday Wear

CLICK HERE OR IMAGES TO SHOP VIONIC

The American Podiatric Medical Association supports Vionic shoes for their excellence in comfort. My mom and I are both huge fans of this brand. We both suffer from plantar fasciitis and need arch support in our shoes. I also appreciate how cute and versatile their shoes are! Sadly, Vionic’s espadrilles are currently on back-order (like the ones pictured.) But not to worry – they have many more cute and comfortable heel options!

In summary, this blog post was about cute, comfy, shoes; the best heel brands you can actually walk in.

Most size inclusive brand: Walking Cradles Shoes

Celebrity favorites: Sarah Flint Shoes

Best for everyday: Vionic

Best for Work: Cole Haan

Comfiest wedges on Amazon: Tom’s

Podiatrist ergonomically designed: Ally Shoes

Versatile and going out: Naked feet Shoes