Wearing high heels can be a pain – quite literally. And, we’re definitely not a believer in the old “beauty is pain” adage. But, you don’t have to give up your heels completely to be comfortable.

You really don’t have to forgo comfort for style. And, here in this article to prove it are the most comfortable heels you can wear, which both look and feel amazing.

Comfortable high heels

You might want to wear high heels because you would like to add extra height.

Or, you may want to add heels for a formal occasion, for work, or because you simply think a certain outfit looks better with heels.

Whatever the reason, you will want to make sure that the heels you choose are comfortable for your feet as well as looking stylish.

 Check out our tips on how to look taller.

The best types of comfy heels to choose

We definitely won’t wear anything that hurts. If you too have turned your back on heels which aren’t kind to your feet, what types of heels should you look for?

The best types of heels for comfort are likely to be kitten heels, block heels and platform heels because either they don’t have skyscraper heels, or they have wider heels, making them easier to walk in. I’d stick with heels around 3-inches or lower.

So, you can certainly combine being trendy and stylish with being comfortable. Plus, lower heels are on trend right now, so you can be comfy and trendy.

We like shopping for heels on Nordstrom and Zappos because you can define your search by heel height and by height type.

Best of all, these styles are definitely on trend right now. Check out this article on the best shoe trends for fall and winter 2023.

What to look out for when choosing a pair of comfortable heels

Have you ever bought a pair of heels which look fabulous, only to find you wear them once or twice and then push them to the back of your closet because they are so uncomfortable.

We know it’s a mistake that we’ve all made. Below are some things to look out for if you want to ensure that the heels you opt for are comfortable:

Choose the right heel height for you

A comfortable height for one woman is not necessarily a comfortable height for someone else. Don’t opt for 4-inch stilettos just because they look good. Generally, a height between 2-inches and 3-inches will be best.

Most comfortable heels: Karen in shirt, jeans and block heeled sandals | 40plusstyle.com

Karen @styledbykaren above opts for block heel sandals. The pink shade gives her classic outfit a playful pop of color.

Recreate her outfit with this similar shirt, jeans and sandals (another option here).

Make sure you get the right fit

It’s always important to get the right fit in any shoe. But, with high heels, you definitely don’t want them pinching or slipping on and off your feet. Just like clothes, you will find that some brands fit you better. As well as shoe size, ensure you opt for the right width for your feet.

Look for soles with cushioning

Wearing high heels puts more pressure on your feet, particularly on the balls of your feet. Look out for shoes which have cushioned soles (or you can always add a cushioned insert).

Want more support from your shoes? Check out the best shoes with arch support.

Opt for natural materials

Leather and suede are often more forgiving for your feet as they stretch and “give” a little wear, and molding to your feet, while manmade materials can be less flexible.

Fonda in peplum top, cropped jeans and mules | 40plusstyle.com

Fonda @savvysouthernchic above chooses block heels with her jeans.

Steal her look with this similar blouse, jeans, mules, bag and necklace.

Pointed or round?

Heels can be tricky to wear. Pointed toes can also be hard to wear if you don’t get the fit just right as they could squeeze your toes. So, when you put the two together, you could find pointed heels are uncomfortable to wear. If you want to make sure that your toes aren’t squished, then you could look for a round toe (or an open toe in warmer weather).

Try on your shoes in the afternoon

Whether you are buying in person or trying on your online purchase, it’s best to try on your shoes in the afternoon. That’s because your feet swell a little and change shape during the day. So, the shoes that fit you in the morning may feel too tight in the afternoon. The ones that fit in the afternoon are the ones you should buy.

Types of comfortable heels to look out for

Now that you are considering what heel height and shoe shape might be best for you, below are some of the most comfortable heel styles to choose from, whether you are looking for heels for an evening out, for a special occasion, for work, or just for everyday.

Kitten heels

Short and slender, kitten heels are generally around 1.5-inches in height, so are definitely more comfortable to walk in than many other types of heels.

Not only that, but they’re very much on trend for the upcoming Spring 2024 season, with designers including Prada and Khaite showcasing small-is-beautiful heels on their runways.

Trotters are a great comfort brand if you need extra support.

Trotters Keely Pump | 40plusstyle.com

Trotters Keely Pump
Amazon / Zappos

We also love Sarah Flint’s heels, which are made with anatomical arch support. If you haven’t discovered Sarah Flint yet, take a look. Her designs are handmade at family factories in Italy.

Sarah Flint Perfect Kitten Pump 50 | 40plusstyle.com

Sarah Flint Perfect Kitten Pump 50

Most comfortable heels: Souri in kitten heeled slingback sandals | 40plusstyle.com

Souri @fabfemme_australia above (read her style interview here) opts for kitten heel pumps with her party outfit.

Steal her look with this similar dress, slingback pumps, clutch and fascinator.

Low heels

Another great comfy heels option, either for work or for everyday, are these Naturalizer sandals below.

They come in a huge choice of colors and have contour cushioning for all-day comfort.

Most comfortable heels: Naturalizer Vera Sandals | 40plusstyle.com

Naturalizer Vera Sandals
Amazon / Zappos

Or, you could try the Margaux pumps (below), which are another true classic. They come in a choice of 11 colors, and were especially designed to answer the question of ‘where the heck do I find a comfortable heel?’.

Most comfortable heels: Margaux pumps | 40plusstyle.com

Margaux The Heel

For a budget-friendly option, LifeStride is a good go-to. The Parigi pumps (below) have traction rubber soles to stop you from slipping.

LifeStride Parigi Pump | 40plusstyle.com

LifeStride Parigi Pump
Amazon / Zappos

Block heels

Because you are giving yourself more surface area to walk on, you will find a block heel much more comfortable to wear than thinner heels.

You may even find that even if you choose a higher pair, they are still easier to walk in because of the width of the heel.

Plus, you’re not going to get your heel caught in anything as you walk, or run the risk of your foot turning over onto its side if you wobble.

If you’re heading into summer, you will be thinking about sandals and shoes which let your feet breathe. For winter, you can look at block heeled boots and closed toe styles.

These Marc Fisher pumps are a classic. They have a fresh take on a block heel, making a heel which is wide yet still manages to be delicate. You could opt for black leather or suede, or a nude style if you are looking for a leg-lengthening effect.

Marc Fisher LTD Zala Pump | 40plusstyle.com

Marc Fisher LTD Zala Pump
Amazon / Zappos

We love the sculptural look of the Vivaia heels (below) which have pressure-relief insoles and heel padding. They come in four colors.

Most comfortable heels: Vivaia Pointed-Toe Block Heels | 40plusstyle.com

Vivaia Pointed-Toe Block Heels

Moving onto a fun, party look, the Boden slingbacks (below) have a mid block heel and will go with all of your going-out looks.

Boden Slingback Mid-Heel Pumps | 40plusstyle.com

Boden Slingback Mid-Heel Pumps

For more inspiration, read our article on what shoes to wear with different styles of pants.

Most comfortable heels: Jess in neutral outfit | 40plusstyle.com

Jess @elegantlydressedandstylish above (read her style interview here) chooses block heels booties with her maxi skirt.

Check out this similar cardigan, skirt, boots (another option here), bag, earrings and necklace.

Angled heels

A similar take on the block heel or the kitten heel which is particularly on trend this year, the angled heel still offers a wide heel or small heel to walk on but with a stylish twist.

Vionic’s pointed toe pumps would be ideal to add interest to a neutral outfit.

Vionic Jacynda Pointed Toe Pump | 40plusstyle.com

Vionic Jacynda Pointed Toe Pump

NYDJ’s booties would go with anything in your closet and feature an interesting angled heel.

Most comfortable heels: NYDJ Gabbe Booties | 40plusstyle.com

NYDJ Gabbe Booties

Comfortable heels for work

As you head into your 40s and beyond, where you work, the way you work, and even if you work may change.

But, if you do need, or want, a pair of high heels for work, the last thing you want is to suffer through your working day with aching feet.

Trotters is always a good go-to for comfortable heels and you will find a number of classic pumps which will add some timeless style to your closet.

Trotters Cassidy Pumps | 40plusstyle.com

Trotters Cassidy Pumps

For more inspiration check out our article on what shoes to wear with different styles of pants

Comfortable pumps

A pair of pumps is a true wardrobe staple that you can wear with everything from a pencil skirt to a pair of jeans.

You can choose any heel height from an inch to four inches – whatever you feel comfortable with.

They’re such a versatile pair of shoes too. You can go with any number of classic options or patterns like leopard print to bring something new to your outfits.

Vionic’s Monterey Carmel pumps feature cushioning for comfort.

Vionic Monterey Carmel Cushion Pumps | 40plusstyle.com

Vionic Monterey Carmel Cushion Pumps
Amazon / Zappos

Comfortable black heels

Most women will have a pair, or several pairs, of black heels in their closet. But, how comfortable are yours?

You could of course, choose any number of styles of black heels, and they will be on trend for many years to come.

Naturalizer’s Everly pumps (below) have a two-and-a-quarter-inch heel and contour technology.

Naturalizer Everly Pump | 40plusstyle.com

Naturalizer Everly Pumps
Amazon / Zappos

For a lower heel, try Trotters Dream pumps with a comfy, cushioned insole.

Most comfortable heels: Trotters Dream Pumps | 40plusstyle.com

Trotters Dream Pumps
Amazon / Zappos

The most comfortable heels for women over 40 | 40plusstyle.com

Emms @beautifuleveryday_uk above chooses classic black heels with her red dress.

She is wearing a dress from LK Bennett. Check out this similar pair of pumps and bag to complete the look.


A platform heel is another idea if you want to add height without walking on a traditional heel. Platforms elevate the ball of your foot as well as your heel, so they tend to be more comfortable to walk in than high heels.

Kork-Ease’s leather sandals (below) feature an interesting ankle strap.

KORK-EASE Stasia Leather Heeled Sandals | 40plusstyle.com

KORK-EASE Stasia Leather Heeled Sandals
Amazon / Zappos

Aerosoles’ heeled sandals also feature a platform sole and would go well with anything from your summer dresses to wide-leg jeans.

Aerosoles Camera Heeled Sandals | 40plusstyle.com

Aerosoles Camera Heeled Sandals
Amazon / Zappos

Comfortable wedges

If you’ve been following us for a while now, you will know how much we love Fly London sandals. They’re comfortable and a little bit quirky, so you can add some individual style to your outfits.

For another Fly London style more suitable for cooler weather, try the wedge pumps (below).

Most comfortable heels: FLY London Yaz Wedge Pumps | 40plusstyle.com

FLY London Yaz Wedge Pumps
Amazon / Zappos

For a dressier take on the wedge, you could try the Nine West pump (below). They come in a choice of neutral shades, and reviewers say they are cushiony and easy to walk in.

NINE WEST Cal9x9 Pump | 40plusstyle.com

NINE WEST Cal9x9 Pump

Wedges are a great option for summer, and the Cole Haan espadrilles (below) are specially designed with foam technology for comfort. They come in a choice of five neutral shades.

Most comfortable heels: Cole Haan Cloudfeel Espadrille Wedge Sandal | 40plusstyle.com

Cole Haan Cloudfeel Espadrille Wedge Sandal
Amazon / Zappos

Comfortable sandals with heels

Sandals with heels are another incredibly versatile shoe.

You can pack them for evenings out on vacation or wear them to more formal occasions such as summer weddings or events.

Or, if you find a comfy pair, you can wear it for day-to-day wear with a pair of jeans and a blazer.

We love the asymmetric strap details on the Rebecca Allen strappy sandals (below).

Rebecca Allen The Block Sandy Sandals | 40plusstyle.com

Rebecca Allen The Block Sandy Sandals

Dawn Lucy in denim jacket, tiered skirt and caged sandals | 40plusstyle.com

Dawn Lucy @fashionshouldbefun above (read her style interview here) chooses on-trend cage-style sandals with her tiered skirt.

Check out this similar top, denim jacket, skirt, sandals, handbag, earrings, necklace and belt.

Most comfortable stilettos

If you do want to add a few inches, then stilettos are usually the highest heels you can choose. Most come in 4-inch heel heights. But, they can be much more difficult to walk in because they feature a tapering heel that narrows at the bottom.

While you are unlikely to want to wear them everyday – after all, even Victoria Beckham has given up her stiletto habit in favor of more comfortable shoes – you might want to don a pair of stilettos occasionally.

Maybe you save your stilettos for times when you know you will be on your feet for a limited amount of time, such as a dinner event.

You can opt for a classic shade, go for something bright like red or pink, or choose a pattern like florals or snakeprint which are bang on trend this year.

Ralph Lauren’s Lanette pumps are well-reviewed for comfort and come in a good choice of colors. Some reviewers say they run small, so you may want to size up.

LAUREN Ralph Lauren Lanette Pumps | 40plusstyle.com

LAUREN Ralph Lauren Lanette Pumps
Amazon / Zappos

Another good choice for a higher heel are the Cole Haan’s Grand Ambition pumps, which have a cushioned footbed.

Most comfortable heels: Cole Haan Grand Ambition Pump | 40plusstyle.com

Cole Haan Grand Ambition Pump
Amazon / Zappos

Comfortable sandals

Everyone needs at least one comfortable pair of sandals for summer. Söfft’s Verdi features wide straps with metallic details as well as a shock-absorbing midsole.

Söfft Verdi Sandals | 40plusstyle.com

Söfft Verdi Sandals
Amazon / Zappos

We also love the woven detailing and interesting heel shape on the Gentle Souls sandals (below).

Gentle Souls by Kenneth Cole Nadia Sandals | 40plusstyle.com

Gentle Souls by Kenneth Cole Nadia Sandals

Flared heel

A different take on the kitten heel, the flared heel is a nod to the 90s and was featured on many of the designer runways for this season. The Franco Sarto pumps (below) come in a good choice of colors.

Franco Sarto Diva Pumps | 40plusstyle.com

Franco Sarto Diva Pumps
Amazon / Zappos

Stacked heel

Usually featuring a wooden sole and heel, the stacked heel starts off wide and narrows towards the base, but it still provides a wide heel to walk on.

We love the elasticated detailing on Everlane’s The Day heel, which comes in a choice of neutral colors.

Most comfortable heels: Everlane The Day Heel | 40plusstyle.com

Everlane The Day Heel

Most comfortable heels for wide feet

If you have wide feet, then an elasticated pair of heels can be perfect. We have more ideas in this article on the best shoes for wide feet.

Most comfortable heels: LifeStride Charlotte High Heel Sandals | 40plusstyle.com

LifeStride Charlotte High Heel Sandals
Amazon / Zappos

Most comfortable designer heels

If you’re thinking about investing in a pair of designer heels, then you’ll want to ensure they are comfortable, you can walk in them, and they are a classic style so you can wear them for many years to come.

You get the iconic Christian Louboutin red on the Mary Janes (below) without a huge stiletto heel.

Christian Louboutin Miss Jane Patent Red Sole Pump | 40plusstyle.com

Christian Louboutin Miss Jane Patent Red Sole Pump

Ferragamo’s block heels are another good choice for comfort. They will never be out of style, which is important if you’re investing in a designer style.

Ferragamo Myra Lambskin Bow Pump | 40plusstyle.com

Ferragamo Myra Lambskin Bow Pump

The most comfortable heels for women over 40 | 40plusstyle.com

How to make heels more comfortable

If you do already have heels in your closet that you would love to wear, but which are uncomfortable, you may still be able to find a solution.

Before you gift or donate them, you could try wearing shoe inserts.

You can find high heel comfort inserts on Amazon. Depending on where you suffer any discomfort, or just to prevent any soreness before it happens, you can find pads for the balls of your feet, or heel grips to stop any slipping on the back of your feet.

Walkize metatarsal pads | 40plusstyle.com

Walkize Metatarsal Pads

Ballotte Premium Grade Silicone Heel Protectors | 40plusstyle.com

Ballotte Premium Grade Silicone Heel Protectors

Dr. Scholl's Ball of Foot Cushions for High Heels | 40plusstyle.com

Dr. Scholl’s Ball of Foot Cushions for High Heels

Dr. Scholl's Stylish Step High Heel Relief Insoles | 40plusstyle.com

Dr. Scholl’s Stylish Step High Heel Relief Insoles

It may be worth trying one of these options before you give up on your heels completely.

What are the most comfortable brands of high heel?

shop the most comfortable heels here:

What are the most comfortable heels you have ever worn? Let me know in the comments below so you can help to turn this into a fantastic resource for other women searching for comfortable high heels. 

Continue reading:

  1. Best Shoes With Arch Support – Comfortable Walking Shoes To Walk In All Day!
  2. The Best Shoes For Swollen Feet
  3. What Shoes To Wear With All Your Dresses

like this article on the most comfortable heels? Share it on Pinterest!

The most comfortable heels for women over 40 | 40plusstyle.com

Feature image by Emms @beautifuleveryday_uk


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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