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6 Comfortable Flats to Wear When You Can’t Wear Heels

I love the look of heels. They give us height, elongate our legs and elevate even the simplest of outfits. But, like many of you, heels aren’t practical for my everyday life – especially these days. What I need is a chic and comfortable flat.

Technically speaking, heels can help us look better in our clothes. They “lift” our bodies up, allowing clothes to drape well and hems to hit appropriately. So when you’re swapping a heel for a flat, you want to follow a few guidelines.

6 Comfortable Flats to Wear When You Can’t Wear Heels

6 Comfortable Flats to Wear When You Can't Wear Heels

updated 2/18/2021

Embrace tailoring

If flats are your go-to, you need to have your clothes tailored.  Have pants and skirts hemmed; you may also have to have some fullness taken out of the leg of your pants so they don’t seem oversized and overwhelm your frame.  

Full-length pants should have a break, which means the bottom of the hem slightly puddles (like a curtain on the floor) on top of your shoe. Bring the shoes you plan to wear to the tailor when you have things fitted to ensure your best length. 

This leads me to my next point.

You will need two pairs of pants.

If you swap between high heels and flats with regularity (say it with me now), YOU NEED TWO PAIRS OF PANTS.

There are no magic pants that you can wear with both heels and flats. You’ll need a few pairs you can wear with flats, and a few you can wear with heels. Tip: Some clients would buy two pairs of their favorite pants and alter accordingly. 

Proportions Matter

When you exclusively wear flats, you have to learn to notice the subtle difference in how clothes lay on the body in a flat vs. a heel. Often, a heel helps garments drape well, and a flat can feel frumpy and off-balance.

For example, full, wide-leg pants are a no-go with flats because they require height to work (for the most part). Conversely, an ankle-length pant that hits right at the ankle looks fantastic with a flat.  

You Need a Point

Look for flats with a pointed or almond shape to to help elongate the line of your body. By doing so, you’re creating the effect you get from heels, and it will help bring balance to an outfit.

And before you say it, no, your big toe should not be shoved into the point of the shoe. If that’s happening, the shoe does not fit you properly. Instead, think of the point as a decoration that helps extend the leg. 

Flats are Super Chic

So play with proportions, have your clothes tailored to fit your specific needs, and keep the line of your leg length with a point, and you’ll be in good shape to swap out your heels for some flats. 

Scroll below for my top picks. There is something for everyone from an investment pair to under a $100 option that is both stylish and comfortable. 

Our Favorite Comfortable Flats 

Our Favorite Comfortable Flats 

Rothy’s, $145

Personal Favorite 

Rothy’s, $145

I bought these specifically for running in airports but they’ve quickly become my overall favorite flat for daily, at home wear. Sustainably made from recycled plastic bottles, Rothy’s mix being eco-friendly with sophisticated style.

They are available in an array of colors and patterns to work in any and every wardrobe.

You need to give them a day or two to break in, but once they do, you’ll love the look and comfort they provide. Bonus points for being machine washable!

Worth the Money

AGL Notch Ballet Flat

Ballet Flat, $350 

These are expensive, I know. In my personal shopping days, AGLs were incredibly popular with my clients who commuted to work and didn’t want to lug a change of shoes with them. I use to wear them on shopping days with clients when I would be on my feet for sometimes 10 hours straight, and they were terrific.

So while the upfront cost of these might seem steep, they may be worth it if you get frequent wear out of them. (Think cost per wear.) I had a pair (similar here) for five years and wore them into the ground before I had to part with them.

I appreciate the feminine shape of these and LOVE the neutral snake print for spring that adds some subtle texture to your outfit.

Chic and Customized

6 Comfortable Flats to Wear When You Can't Wear Heels

The Pointe, $258

Available in nine gorgeous shades and prints (including the above Zebra Haircalf that I am dying over), Margaux is an incredible shoe brand that mixes chic styling with comfort. 

Here’s the BEST part, their entire focus as a company is fit, so they offer extended sizes, multiple widths including narrow, medium and wide and made to measure options.

Easiest to Dress Up

J.Crew Gemma ballet flats in leather

Ballet Flat, $75

Spend any time on Pinterest searching for inspiration outfits and you’ll quickly find yourself frustrated. The outfits are cute, but the heels are sky high. What to do? Go with a pointed ballet flat, in a simple style. 

These will help mimic that long line of the leg a heel creates. 

The J. Crew Gemma Flat is one of their Top Rated, Five Star Reviewed shoes and they are currently on sale for $75 in black and chestnut

Best Loafers 

Madewell The Frances Loafer

Loafer, $130

I read hundreds of online reviews every month, thousands every year, and I have never shared one in a post before today. 
This made me laugh out load: 

They are the shoe equivalent of Paul Rudd- handsome, wholesome, practical and somehow, works with everything.

What a compliment!

I for one am delighted to see loafers rise in popularity and equally thrilled that they are starting to take inspiration from menswear while providing a slimmer shape for a woman’s foot. Pair these with straight-leg pants, and have the hem puddle just slightly on the top of the shoe.

These Madewell France Loafers come in black and mahogany, available in half sizes and rave reviews for comfort after you break them in. 


Under $100

Born Brin Ballet Flat

Ballet Flat, $80

The challenge with most under $100 flats is that they either look great or they are comfortable but look like orthotics. But we want both comfort and style in one, and these BORN ballet flats are so sweet.

You can wear them with everything, including straight-leg trousers, ankle pants, jeans, and skirts. I’m featuring basic black above, but they are available in several spring ready colors, like soft grey, yellow and a light beige. 


Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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6 Comfortable Flats to Wear When You Can\'t Wear Heels

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Thursday 18th of February 2021

I have such shoe envy! I wear a size 12 and most pointed toe shoes look like clown shoes on me. Any thoughts on the Big Foot style? I know you can’t possibly cater to everyone but curious if you have a suggestion to keep the circus look at bay- anyone else have ideas?


Thursday 18th of February 2021

I am disabled and on a walker so I must wear flats. I don't wear pants anymore so I don't have to concern myself with hemming pants. Longer skirts with flats look the best on me. Thank you so much for your advice on these cute shoes!


Thursday 18th of February 2021

Thanks for this post, Megan. I knew I needed to upgrade my flats collection but apparently I was waiting for someone to tell me what to do!


Thursday 18th of February 2021

Rothy's are NOT size inclusive. They sell no wide width shoe. Yes, I know they tell you to go up a half size. But when you read the comments, most of them are from women who followed that advice and ended up with shoes that did not fit. You are a style influencer, Megan. Maybe you can speak to Rothy's on behalf of wider footed women. I would surely buy a pair. They are lovely

Megan Kristel

Thursday 18th of February 2021

I'm not sure I'm loving the tone of this comment. Unfortunately, I don't have a direct line to Rothy's corporate. Not all brands are going to be for all people, and there is nothing I can do about that. There are other options on this list that include wide sizes.


Thursday 19th of March 2020

I love the look on other women. I’ve tried several pairs (mind you not overly expensive one) my issue is that I must wear orthotics in my shoes and flats don’t allow for the addition. Any suggestions?


Monday 9th of March 2020

Any recommendations for "supportive" shoes? I'm, apparently, entering that phase of my life now at least according to my doctor. Everything seems so dowdy.


Wednesday 4th of March 2020

just wanted to say HI! I would love to buy Rothy's but they are NOT size inclusive. They have no wide widths. I know what they say about going up a half size, but most reviews I read from people with wider feet said this trick did not really work (and they were sorry they tried it!)


Wednesday 4th of March 2020

Megan: What do you wear on your feet *inside* these shoes? I usually need to wear a "sock" of some sort, so my sweaty feet don't stick to the inside of the shoe. I wore knee-highs/peds for years back when pantyhose were still a must, but I sometimes feel like they make my feet sweat more and they get stinky, which makes your shoes stinky. And I haven't found a nude, no-show sock that stays on my feet inside shoes. Any tricks or tips?


Wednesday 4th of March 2020

I love AGL, and yes, they are worth the price. I was wondering how to get the wardrobe checklist we we are already signed up for E-mails?

Megan Kristel

Wednesday 4th of March 2020

Thanks Carol - and just send me an email to [email protected] and I'll forward you a copy of the checklist. :)


Wednesday 4th of March 2020

I love the Margaux ballet flats! However, a warning; they will charge you upon ordering and it can take weeks for them to arrive. I also found them to run about a half-size large but others don’t seem to have that problem. I love all MGemi shoes as well. They have comfortable heels as well as flats. I particularly love their boots! Everything is packaged so nicely also.

Megan Kristel

Wednesday 4th of March 2020

Good tip on the Margaux flats, thanks! And I keep forgetting about MGemi - love them!!!!


Wednesday 4th of March 2020

I'm so excited to have found you Megan! Great styling tips for flats. I have one personal fit "no go" ~ toe cleavage. LOL I have discovered Dr. Scholl's flats and loafers. So many styles, colors and prints. Even though their memory insoles are comfortable, I pull out theirs and add my plantar fasciitis insets and I can walk all day on day one.


Friday 1st of November 2019

Maybe it's because I have flat feet, but super flat shoes cause back, knee and ankle pain almost as much as super high heels! I prefer a 1 to 2 inch heel for comfort. LOVE a kitten heel, when the sky high heels are just not in the cards for me that day. I wish I could wear the cute flats you show us.


Monday 21st of October 2019

Hi Megan! I was thinking about getting the Rothy's but some of the comments are saying to size up. Do you find them to run small or do you typically order your go-to size?


Thursday 10th of October 2019

What should the proportion of a skirt be to wear with pointy toe flats? I always think my skirts look better with heels, though flats would be my preference. For example, can you wear the Rothy’s with a pencil skirt and blazer?

Megan Kristel

Friday 11th of October 2019

Because everyone has a different shape and proportion there isn't a universal length. However, GENERALLY speaking, you may want to shorten your skirt to wear it hits when you wear heels. I often wear pointed flats with dresses, it's actually considered kind of french-girl-chic. Because I'm tall, I keep the length to the very top of my knee, if you are shorter, a little bit above. You just want to show enough leg to maintain the line of your body.


Thursday 10th of October 2019

How do they wash? Any shrinking?

Megan Kristel

Friday 11th of October 2019

They wash well and no shrinking because you air dry them :)


Thursday 10th of October 2019

Great article and cute shoes, but I wish you would have included some pictures of the flats worn with actual outfits. The tips are helpful, but it's tough for me to visualize just based on the descriptions. Ironically, even the ads that popped up when I was reading this were all of models wearing high heels!

Megan Kristel

Friday 11th of October 2019

Pictures are challenging because I'm a one woman show and showing things on my body isn't always helpful because of my height and proportions.


Thursday 10th of October 2019

Ooooh! I am so glad that you published this list! I love flats! - I have "problem feet" which means that heels kill me. My daughters have the same problems as me and I will share this list with them - maybe it will make them feel better to know that there are chic shoes out there which will make them look like a million dollars - without slowly killing them with painful feet and back pain.

Megan Kristel

Friday 11th of October 2019

Happily, there are more chic flat options today than ever before!


Thursday 10th of October 2019

I now have 3 Rothy’s and I love them!! Most recently I got the same leopard print you have pictured. I LOVE them and get so many compliments! I finally got up the courage to wash my mustard pointe the other day. Amazing!!

Megan Kristel

Friday 11th of October 2019

Yes!! I was worried to wash too but couldn't be happier!

Susan Anderson

Thursday 10th of October 2019

I was just thinking about asking you this very question. I've been coveting Rothy's The Point for a while. It may be time to pull the trigger. Thanks for all your wonderful advice. I enjoy all of your posts!

Megan Kristel

Friday 11th of October 2019

Thanks Susan! Just remember they need a day or two to adjust to your feet.

Kristin J Arnold

Thursday 10th of October 2019

As always, love your suggestions. I love M.Gemi flats too! A little pricey, but the fit and wear is fabulous! Italian leather and design. Yummy straight out of the box!

Megan Kristel

Thursday 10th of October 2019

Yes! Great recommendation. I love them, especially with sleeker pieces you might wear to the office. Worth the money for sure :)