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

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.

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

 

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.

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!

Buckle 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. 

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.

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.

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

Loafer, $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. 

Skimmer 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. 

_________________________________________________________

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. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please consider following on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

_________________________________________________________