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

Lately, the most popular question in my inbox is about flats. Specifically, how can we recreate all the lovely inspiration outfits we see in magazines, Pinterest, and even here on this site, when heels are just not an option.

I do love the look of a heel, how they elongate the leg and make us stand up straight (assuming they’re a pair we can walk in). But the truth is, like many of you, in my real life heels are reserved for work days and the rare dress up night.

Otherwise, I’m in some kind of a flat, be it a sneaker, boot or a feminine flat. 

From a technical perspective, because a heel physically “lifts” the body up, you get a lot of benefits. Of course, you look taller, you can often look leaner, and clothes can hang better. The right heel can bring balance to an outfit. 

But! There are some things we can do to create the same benefits with flats. 

How to Wear Flats Instead of Heels

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

Embrace tailoring

If flats are your go-to, and you have to completely avoid heels, you need to have your clothes tailored. You’ll absolutely need to 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. 

Full length pants specifically should have a break, which just means the bottom of the hem puddles (almost like curtain on the floor) on top of your shoe. 

But be sure that everything else is in proportion, a local tailor can help you with that. And be sure to bring the shoes you plan on wearing when you have things fitted. 

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.

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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 used to 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 will 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, one that hits right at the ankle, looks fantastic with a flat.  

You Need a Point

Look for flats with a pointed toe 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 sit in the point of the shoe. If that’s happening the shoe does not fit you properly. Rather, the point is just 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 long with a point and you’ll be in good shape to swap out your heels for some flats. 

Scroll below for my top picks. From an expensive investment pair, to under an $100 option that is as chic as it is comfortable, there is something for everyone. 

6 Flats to Wear When You Can’t Wear Heels

6 Flats to Wear When You Can't Wear Heels
Rothy’s, $145


Rothy’s, $145

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

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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!

6 Comfortable Flats to Wear When You Can't Wear HeelsBuckle Flat,$380 

These are so expensive, I know. Back in my personal shopping days, AGLs were incredibly popular with my clients who had a commute 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 wonderful. 

So while the upfront cost of these might seem steep, they were often they might be one of the only shoes you wear. They come in an array of color combinations, but for what you’re spending I would stick with classic black so you can get as much wear out of them as possible. 

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

The Pointe, $195

Available in 10 gorgeous prints (including the above Zebra Haircalf that I am dying over), Margaux is an incredible shoe brand that mixes chic styling with comfort. Prices average under $200.

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

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

Skimmer Flat, $150

A slingback and a flat had a baby to create this feminine shoe that pairs beautifully with lightweight skirts, dresses, or ankle pants. Cole Haan still makes a sensational shoe, that is stylized enough to look modern but simple enough to have for years.

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Get these cleaned and resoled as needed to keep them in tip-top shape season after season. 

6 Comfortable Flats to Wear When You Can't Wear HeelsLoafer, $130

I 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 Trotter Pointed Loafers are available in black and  in black and cognac for $99 in this similar style here

6 Comfortable Flats to Wear When You Can't Wear HeelsSkimmer Flats, $99

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 Naturalizer’s fit the bill.

You can wear them with everything, including straight-leg trousers, ankle pants, jeans, and skirts. They are available in a soft beige (above), black and a drop-dead gorgeous burgundy snakeskin.  I’m sending you to the QVC website for these because they have the best selection of sizes. 


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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

25 thoughts on “6 Comfortable Flats to Wear When You Can’t Wear Heels”

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

  1. 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!

  2. 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!!

  3. 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.

  4. 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!

    • 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.

  5. 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?

    • 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.

  6. 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?

  7. 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.

  8. 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.

  9. 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.

  10. 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?

  11. 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?

  12. 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!)

  13. 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.

  14. 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?


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