Last Updated on January 19, 2026 by Martina McKeough
I’m a total high heel lover, but let’s be honest whilst they look great they aren’t always comfortable. So with that in mind I’m always searching for the most comfortable heels (and flats) that actually feel good to walk in. Whilst I’m no longer in my twenties I still want to wear stylish shoes but my feet need cushioning, support and a design that won’t leave me limping at the end of the day.
If you are like me and refuse to suffer for fashion then hopefully you’ll love these high heel picks that are designed to work with your feet and not against them.
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Comfortable High Heeled Pumps
Let’s start by looking at high heeled pumps that are the workhorse of your shoe wardrobe. These are great for wearing in the office but can be dressed up for a night out.
If you are in the know you’ll be looking at brands like Clarks, Naturalizer, Vionic and Aerosoles who all make great looking shoes that maximise comfort and minimize pain.
Aerosoles Besty Pumps
These Aerosoles pumps come in a huge range of colors so you can find a pair that will match just about any outfit.
These are definitely mid heeled shoes which means that your feet are less likely to feel the strain. They have a chunky heel and also an Ortholite foam insole for cushioning to make them easier to wear.
Buy these and you have a great closet staple that will look stylish but keep your feet comfortable.
High Heeled Sandals That Won’t Hurt Your Feet
When the weather is finer it’s time to get out your sandals but where heels are concerned you need to think a little more strategically if you want to wear them without pain.
Choose a mid heel height so you aren’t punishing your feet with akward angles and pick ones that have a cushioned sole. I also like to look for more secure straps rather than thinner ones as they are more likely to keep my feet in the sandals securely. With that in mind these Vionic heeled sandals fit the bill.
Vionic Women’s Chardonnay Heeled Sandal
Once again these come in a range of colors so you can pick something that will suit your taste.
What Vionic do that is great is have orthopedic technology included in their shoes so that comfort is prioritized.
These sandals have everything from a deep heel cup, to arch support and great cushioning which means your feet are less likely to suffer for fashion.
Wedge High Heels That Take the Strain
Want the height but less pain and discomfort? Well then take a look at wedge shoes which are easier to walk in and give the illusion of height without the need to walk around on a pointy stiletto.
You can buy wedge heel boots, shoes, sandals and even sneakers to give you extra lift which are also really comfortable to walk in.
Vionic Venus Marina Wedges
These Vionic wedges come in a number of different colors and are perfect for the warmer weather.
These are especially good if you suffer from plantar fasciitis or achilles tendonitis. I find Vionic shoes some of the most comfortable on the market because of their arch support.
Block Heeled Shoes To Give You More Support
Another trick that you can use is to buy shoes that have blocky heels. The more extensive the heels on your high heels the more likely they are going to be easier to walk in. They are usually also more comfortable because of the extra stability.
These patent block heeled shoes are high but because of the heel shape reviewers found them to be really easy to wear.
Chunky Block Heeled Patent Shoes
The Most Comfortable Stiletto Heels
Let’s face it high stiletto heels are never going to be as comfortable as block heels, pumps or wedges but there are certain things you can do to mitigate any problems.
As I mentioned earlier buying from a brand that cares about foot health makes a difference. I also tend to look for shoes made from softer materials so they are less likely to cut into my feet and with lower heels so they take pressure off the ball of the feet. I also try and ensure they are cushioned as well.
This pair from the Naturlizer are a good example of choosing stiletto heels more wisely.
Naturlizer Anna Pointed Toe Pump
Low Heeled Shoes That Still Look Great
Finally I had to mention lower heeled shoes that are all the rage right now. Low heels can still look stylish but come with less pitfalls that higher heeled shoes. I love sling-backs and kitten heels for a sophisticated look that works for day or night.
Sam Edelman Bianka Pump
Which Ones Will You Choose?
Finding the most comfortable heels doesn’t mean sacrificing style for support. With the right pair, you can feel confident and comfortable from morning meetings to evening events. Whether you prefer block heels, cushioned soles, or supportive straps, there’s a perfect match out there for your feet. Invest in quality, know what to look for, and your heels will become your new all-day favorite.
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