Finding comfortable heels

Finding comfortable heels

I vividly remember my very first pair of heels. I was 15 and begged my mom to the point of drilling a hole in her head until she finally caved in. I was the happiest teenager alive going home with a very trendy pair of black shoe boots! My hands were shaking with excitement when I was fastening the little silver buckles the following morning. By the lunch time my excitement not only evaporated but I was ready to chew my feet off with no anesthetic just to get out of those shoes. That was my first taster of the proper struggle that most women endure when they want to look taller! Those shoes put me off heels for years afterwards. But then I started experimenting with heels again and discovered that not all heels are torture for your own money. I am now a heel addict as I am at my most confident in heels. I can have a pair of old jeans and a simple t-shirt but a pair of heels does wonders to that look for me.

These days one of the most frequent questions my clients ask me about shoes is where to buy high heels that don’t kill your feet. I will disappoint you straight away – I am not going to point you in the direction of a magic shop that sells heels that feel like slippers. I personally do not believe there is one brand out there that each and every woman will find comfortable.

However, I will outline all the factors that dramatically increase the chance of finding shoes that you’ll happily keep on for the day (or night!). 

Here are some tips that proved to be very effective for both myself and my clients.


Number one thing I always pay attention to is the material the shoes are made out of. Your best bet is to aim for leather insole and leather upper. Your feet don’t sweat in them as much as they would in man-made materials (and sweat is the most effective shortcut to blisters!). Also, leather tends to mold to your foot shape over time making them even more comfortable while man-made materials rarely have the same flexibility.

Good quality shoes often come with the leather sole but the sole has very little to do with the comfort of the shoes so it’s not something I take into consideration. In fact, leather sole is a lot more high maintenance and you’ll need to have them re-heeled and re-soled a lot quicker than you would with man-made sole. Man-made soles, however, can often be very slippery so the best fix for that is to rub the sole with the sand paper. Works a treat every time!

If you are buying court shoes

Court shoes are a staple in most work wardrobes so are something most women have to shop for at some stage. Pay attention to the following:

• Make sure your foot doesn’t slip out when you walk – slipping out of shoes is just as bad as having them a size too small. Also make sure you’re not curling your toes for a better grip, the shoes should feel secure without any extra efforts on your side. 

• Look for the designs that cover most of your toes – this provides for a better fit and reduces the risk of your foot slipping out. The more ‘toe cleavage’ the shoes have, the less grip they have on the foot (having an ankle strap can counteract this). If you want toe cleavage (I have to admit it does look sexy!), make sure the sides and the back provide enough support to keep the foot in.

Having said that, experiment with different cut-outs if your toes have sore spots. I have very sensitive knuckles on my fourth toes so often have to play around with toe cleavage to get the fit right. 

• Always try both shoes on! Most stores have the right shoe on display so they tend to be a lot looser. I usually ask for a fresh pair to make sure the shoes stretch out equally.

finding comfortable heelsfinding comfortable heels


• If the shoes feel very tight, are catching you on sore spots like bunions or put pressure on one or more of your toes, they will never stretch to the point of being fully comfortable! Don’t be fooling yourself into thinking you’ll break them in and they’ll be fine. I am often asked how I manage to spend the day in my heels and I’ll tell you this – I only buy heels that are comfortable in the shop.

• If you already made the mistake of buying tight shoes, try this:

  • Put on sports socks and place the shoes on the radiator to warm them up. If radiators are switched off, use the hair dryer. Put the shoes over socks while they are warm and wear them for a while around the house. Repeat if necessary. In most cases shoes will get a bit roomier.
  • Take shoes to a professional cobbler for stretching.
  • Tape your third and fourth toes together with a plaster or medical tape. A few of my clients swear by this trick. They say any discomfort and tightness is immediately gone.

• Almond or round toe give more room for the toes making the shoes more comfortable, but the pointy toe works better on elongating the leg. If you have wide feet, finding comfortable pointy toe heels will be very hard so almond toe is your next best option. I have examples of almond toe and round toe below. If you prefer to stick with the round toe, go for a block heel – it looks a lot more contemporary.

almond toe shoesround toe shoes

If you are buying high-heeled sandals

• Make sure the straps are not too thin as they will be cutting right into your skin – a dreadfully uncomfortable feeling! The thinner the strap, the less support your foot has making the straps the only point of grip. Barely-there strapped sandals look elegant and delicate. For the first hour. So look for sandals that give your foot plenty of support. T-bar is also a good feature that increases the likelihood of comfort.

black strappy heelsblack strappy heels

• Soft leather straps are much kinder to skin than non-leather material so don’t compromise on quality.

• Get the right size – sandals that are a tad too big or too small are a recipe for disaster. If they are too small, the heel will be spilling over the back and your toes will feel squashed. Too big and your foot will be sliding forward without the necessary support on the arch. Blisters will be there before you know it. This sounds like a very obvious piece of advice yet so many women fall between the sizes and still decide it’s a good idea to be buy the shoes that don’t come in half size.  If you fall between the sizes, only buy from brands that offer half sizes. I am 4 1/2 UK, I sometimes get away with a 4 and go for size 5 in boots to allow room for socks. But I always watch the size like a hawk to make sure I get the fit right.

Breaking in the shoes 

If you need to break in the shoes that feel a bit stiff, wear them with tights for the first few times. You will end up with blisters if you do that on bare feet. 

If you are sore on pressure points or the back of the shoes feel a bit too snug, use clear gel plasters from Scholl or any other brand that does similar plasters.  They are almost invisible, have a bit of cushioning for pressure relief and eliminate friction between the shoe and the skin. Way more efficient than normal plasters! 

I also find them great for using at the back of the foot when you are slipping out of the shoes. 


One of the other key factors that makes a world of difference to the comfort of the heels is the insole padding. It provides great cushioning for the ball of the foot and makes shoes much more wearable for longer periods of time. You can, of course, put those gel inserts but they never provide the same level of comfort – they make the shoes much tighter and if you are not wearing tights, silicone creates a very unpleasant friction burning against bare skin. However, if you have to use insoles, I would highly recommend Aldo for a good selection of options. I particularly like their gel ones (completely different to silicone cushions!) that have soft fabric on the surface and adhesive silicone cushion underneath. They provide a decent amount of cushioning (they are much thinner than the cushions) and pressure relief while being discreet enough to wear even with sandals. And retailing at 8 euro, they won’t break the bank!

aldo gel insoles

Leather, suede or patent?

Suede is usually the softest of the three and molds to your foot the fastest. Some high quality leathers can be butter soft and very comfortable as a result but they also lack in durability due to the softness of the material.

Patent is a lot less flexible than leather or suede, even when it’s real leather.

I usually give preference to suede if I am looking for shoes that I’ll be doing a lot of walking in. I only got  for patent for shoes that I know I won’t have on for the whole day. I have some very comfortable patent shoes but they still can never rival the comfort of suede or soft leather.

So consider the material carefully before you buy!

Stiletto or Block Heel

Stilettos might look elegant but there is nothing sexy about the Bambi walk down the street. Stilettos do require a good bit of practice and a sturdy foot. Luckily, the block heel has become huge over the last couple seasons and is not going anywhere for another while.

There are certain circumstances when you can’t beat a stiletto (like in a skirt suit for work or a slinky evening dress) but more often than not you can find a pair of block heels that will look feminine and go with most looks. So if you want to capitalize on the benefit of having your legs elongated but don’t want to suffer for it, the block heel is your best option.

block heel sandals

block heel sandals

block heel sandals



Buy shoes in the evening

And the last tip – I religiously follow the rule of not buying shoes in the morning. For anyone prone to feet swelling (my toes often look like cocktail sausages by the end of the day) this can make a world of difference to the fit of the shoes. Buying footwear in the afternoon or evening reduces the risk of buying shoes that will make your poor feet wish every morning they never left the house.

Brands I personally wear

I have a thing for shoes so I do own a lot of heels and boots. Here are the brands that I personally find very comfortable:

  • LK Bennett (I don’t own a single pair of their shoes or boots that would be hurting my feet)
  • Karen Millen (the rise of their shoes fits me perfectly so every pair of their heels I put on fits me like a glove)
  • Hobbs (again, another brand that never disappoints me in regards to comfort)
  • Elie Tahari (not a cheap brand but totally worth it)

Most shoes from these brands have leather inside which makes them so comfortable. They do come at a cost but at least you know what you are paying for. At the end of a long day you’d pay any money to get some relief from sore feet so if there is only one thing you invest in, make it quality shoes.

Shoe brands below don’t always do leather but are still very comfortable:

  • Nine West (their Flax model in particular is super comfortable)
  • Marks & Spencer (hidden gem on the high street! Look out for their Insolia range which has superb built-in cushioning to the insole)

These brands are for reference point only, ladies! Any time I mention heels, I get bombarded with questions where to get them. These brands work for me and worked for numerous clients but everyone is different. If you can recommend a brand that you tried and found very comfy, please share below! You know, for good karma! 😉

I hope you find these suggestions helpful! If you feel that finding comfortable heels is like being on a quest to find the Holy Grail, don’t give up just yet. See if any of these tips make a difference and if they don’t, you can go shopping for fancy flats with a clear conscious!

Don’t forget to share this post with your friends! Every woman could do with a pair of comfortable heels! 🙂

Natalie xx



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