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

You really don’t have to forgo comfort for style. And, here 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.

 More tips on how to look taller here

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.

The best types of comfy heels to choose

I 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.

Best of all, these styles are definitely on trend right now. Check out this article on the best shoe trends for spring and summer 2019.

So, you can certainly combine being trendy and stylish with being comfortable.

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

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

Kitten heels

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

Not only that, but they’re very much on trend for spring and summer 2019, with designers including Balmain, Dior and Giorgio Armani showcasing small-is-beautiful heels on their runways.

This pair of Greatonu slingback kitten heels are recommended on Amazon for their classic style and comfort.

This is a great budget-friendly option if you are looking for a pair which don’t cost too much, but don’t scrimp on comfort. Plus, they come in 21 different shades and patterns.

Comfortable Heels - Greatonu Womens Slingback Dress Pump | 40plusstyle.com

Greatonu slingback kitten

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.

I’m loving the ones these booties is wearing in the image below. They are sold out but these booties look very similar.

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

The Most Comfortable Heels that Look Hip and are Comfortable to Wear | 40plusstyle.com

If you’re heading into summer, you will be thinking about sandals and shoes which let your feet breathe.

These Sam Edelman Holmes style sandals 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.

They have a 2-and-a-quarter inch heel as well as great reviews on Nordstrom.

The best ankle strap sandals for summer | 40plusstyle.com

Sam Edelman Holmes

Another shoe to consider are these comfortable sandals by Finn, one of the brands often recommended for arch support.

These one are airy and will look good with many outfits.

Comfortable sandal shoes with heel by Finn

Finn comfortable sandals

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.

Naturalizer 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.

The Naturalizer Whitney pump is one of the brand’s classic styles which you will usually find in stock. I like the classic black leather (below) but there’s also a patent black leather and a taupe here. They have arch and heel support as well as breathable lining and cushioning.

This style has four-star reviews from hundreds of women on Nordstrom.

Comfortable pumps for women over 40 | 40plusstyle.com

Naturalizer Whitney pump

Low heels

Another great option, either for work or for everyday, are Everlane’s classic day heel.

You’ll always find this style in stock, although new colors are added each season. You can also opt for leather or suede.

They are made from Italian leather and feature a cushioned insole and elastic back to stop slipping.

These have great reviews on Everlane’s website.

everyday heels for women over 40 | 40plusstyle.com

Everlane’s classic day heel

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.

If you prefer a narrower heel, the Via Spiga Nikole pump falls between a kitten heel and a stiletto with a height of 2-and-a-half inches.

It’s lovely in black, but also comes in a range of classic neutrals and brights if you would like a different color.

mid size heels for women over 40 | 40plusstyle.comVia Spiga Nikole pump

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.

The Lifestride Pargi have cushioned soles, a flexible sole and a heel height of 2.5 inches, making them a good everyday option. Plus, you can choose from 27 different colors.

LifeStride Women's Parigi Pump | 40plusstyle.com

Lifestride Pargi

Comfortable platform heels

If you’ve been following me for a while now, you will know how much I love my Fly London platform sandals.

I have the Yala wedge which is 2.25 inches in height, but it feels lower because there’s a 1-inch platform.

They’re comfortable and a little bit quirky, so you can add some individual style to your outfits.

Comfortable Heels - FLY London Women's Yala Perforated Wedge Sandal | 40plusstyle,com

Fly London

Comfortable sandals with heels

Sandals with heels are another incredibly versatile shoe.

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

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

Eileen Fisher has a classic open-sided sandal with a 2-inch heel to add a little height without being uncomfortable. There’s a pentagonal heel which adds interest along with a rounded toe and a stretchy ankle strap. This style has five-star reviews on Nordstrom.

Eileen Fisher pumps | 40plusstyle.com

Eileen Fisher pumps

Comfortable wedges

Another great option for summer daywear, or to pack for your vacation is a pair of comfortable wedges.

Vionic is always a good option to try for comfortable footwear.

This Zamar Wedge Sandal style is new for this summer. They have the American Podiatric Medical Association Seal of Acceptance because of the contoured footbed with arch support and orthaheel technology which is designed to offer balance, stability and support.

Zamar Wedge Sandal | 40plusstyle.com

Zamar Wedge

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 which 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.

These heels from Sam Edelman have 4-inch heels, 4 millimeters of cushioning and even higher reviews.

This is a classic style you’ll always find from Sam Edelman, but there are new colors and textures added each season.

You can opt for a classic shade, go for something bright like yellow or lilac, or choose a pattern like snake print which is bang on trend this year.

Comfortable Heels - Hazel Pointy Toe Pump | 40plusstyle.com

 Sam Edelman heels

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.

You may also like:

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. 

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The Most Comfortable Heels | 40plusstyle.com

Feature Image by: @thewardrobeconsultant 

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