Pointy-toe shoes are a very different beast from your average shoe as the room at the front is significantly less. This means you need to be spot on when buying the right shoes when shoe shopping or they are going to hurt. If this is your problem I’m going to show you how to make pointy shoes comfortable and avoid foot pain where possible.
The tips and tricks I’m going to show you are suitable for men’s and women’s shoes with a few exceptions. They can also help whether the shoes are flat or if you like to wear heels.
Before I begin it is worth talking about why you might be having problems in the first place.
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How Should Pointed Toe Shoes Fit?
When you go shopping for a new pair of shoes it is important to find a comfortable pair by taking your time trying on a number of different styles and walking around in them to assess the fit. This is especially important when you are looking to buy pointed toe shoes.
Pointed shoes mean that the toe box of your shoe has less room than an average shoe. This can look chic or fashionable but this lack of room can cause issues.
To make sure you don’t suffer for fashion you need to think a little more about the fit of the shoe and the shape of your foot.
To find the perfect pair you need to be able to fit your feet into the shoe and have room to allow your toes to move inside. Do not buy a pair of shoes where your toes are cramped or feel like they are rubbing the sides of the shoe.
Pay attention to your toes and where they are sitting in the shoe. Our ancestry dictates partly where our toes sit. Some of us will have toes that are almost all the same size across the foot whereas others will find that their big toe is the largest toe and the other toes start to get smaller in a sloping style.
If you have a sloping style toe arrangement you will probably find that pointed shoes are easier to wear than those that have a similar toe shape all the way across. If you have the latter you may find you need to size up to get the shoe style that you want.
Why Are Pointed Shoes Uncomfortable?
Pointed shoes feel uncomfortable to many people because they buy the wrong size or shape of shoe and this causes their toes to rub on the size of the shoe causing blisters or shoe bites.
The problem is worse if you have chosen to purchase high heels because the downward pressure of gravity forces your foot forwards toward the toe box area. Unless this is corrected you are going to find that the balls of your feet hurt and your toes feel squished into a narrow area where they have little room to move.
Wearing poorly fitting pointed shoes consistently can lead to hammer toes, neuromas, blisters, and foot pain.
How Do You Break In Pointy Toe Shoes
If you want to know how to make pointy shoes comfortable then you may need to break in your shoes.
To break in your pointy-toe shoes you are going to need to assess where the problems lie in order to fix them. Unlike normal shoes just wearing them around the house or stretching them may not solve all your issues.
Making heels more comfortable may require different solutions to what you may do if you have pointed-toe flats with a problem.
I will discuss each method for solving painful shoe issues and when they can be used so you can make a decision on what you want to do based on your particular shoes.
Should You Size Up in Pointy Shoes?
Remember that where pointy shoes are concerned you may need to size up from your normal shoe size. Expect to wear at least a size larger in some styles to accommodate your feet.
The key is assessing your size not on what you would normally wear but by trying out the shoes and seeing if they feel comfortable on your feet before committing to your purchase.
How Much Room Should Be In The Toe of a Pointy Shoe
Generally, if you want comfortable shoes you would expect there to be around half an inch of room at the front of your shoes for your toes to sit without causing pain or rubbing.
You will need to measure this point from your longest toe to get the room you need. In some feet, this may be the second toe which can sometimes be larger than the big toe.
How To Stretch Pointy Shoes
So if you want to know how to make pointy shoes comfortable your first step is to assess whether you have bought a pair of shoes that don’t have sufficient room in the toe box for your toes to move.
If this is your problem then stretching the front part of your shoe can help to give you that extra room you need. Just take note that when you are stretching your shoes you need to be mindful of the shape of your shoe and the need to keep that looking good as well.
As pointed shoes have a triangle-shaped front you don’t want to stretch it so that it is misshapen and ruins the look of the shoe.
In order to stretch your shoes there are simple steps you can take such as:
- Wearing thick socks
- Using a shoe stretcher
- Buying stretching spray
- Heating your shoe
- Using the Ice method
The Thick Sock Method
This method is one of the simplest as all you need to do is put on a pair of thick socks and walk around the house in your shoes to break them in. Do this for short periods of time initially to prevent hurting your feet and gradually build up to longer periods until your shoes have stretched or molded to your foot shape.
Use a Pointed Toe Shoe Stretcher
Shoe stretchers are great devices that can help you to fix your footwear at home without visiting a shoe cobbler. This metal shoe stretcher is more robust than a plastic shoe stretcher and has a great shape which has been specifically designed for high heels. All you need to do is place it into the toe box of your shoe and turn the mechanism to start the stretching process. When it is removed you should have roomier and more comfortable shoes.
Stretching Spray To Help Make Shoes More Comfortable
If you want to know how to make pointy shoes comfortable then Stretching spray is another easy product to use that can help to create more room for your toes in new shoes. All you need to do is spray it on the inside of your shoes in the problem area and then start walking around in your shoes to allow the stretching spray to alter the size of your toe box. This shoe stretch spray by Fiebings tends to work well and can make your shoes slightly larger and more comfortable.
Heating Your Shoes
Heating your shoes can also help to stretch the leather and give you more room for your toes. Aiming a hairdryer in short bursts at the problem area and then wearing the shoe whilst it is still warm should do the trick. Just beware that heat can cause cracking on your shoes so if you are going to use this method do it for short periods of time and make sure the blow dryer is at least 6-8 inches away from the shoe.
Using Ice to Stretch a New Pair of Shoes
Filling a freezer bag with water and placing it in the toe area of your shoes can also help. Place your shoe in a plastic bag and then in the freezer and the water will expand and turn to ice. This can help to stretch the toe box. Leave your shoes inside the freezer for 24 hours and when you remove them let the ice melt. You should now have more room in your shoes.
Buy Toe Filler Inserts
Not all pointed-toe shoes or high heels need stretching to solve the problem. Sometimes gravity forcing your feet forward inside your shoes can be the issue. If this is the case you need to buy foam toe puffs or toe filler inserts.
These are padded inserts that you place in the front of your shoes to stop your feet from sliding forward and to prevent friction from the shoe material. They can also be used to help when your pointed-toe shoes are too big.
Just pop the inserts into the pointed section of your shoe to enable you to wear your footwear without pain.
If you don’t have the time to get any inserts for your shoes you could use cotton balls as an easy short-term fix.
Buy Toe Sleeves to Stop Your Shoes From Hurting
Toe sleeves are another great device that you can use particularly if you are experiencing foot pain from a particular toe. There are different toe sleeves that can fit your big toe, second, third, and fourth toes, and even your little toe.
Some toe sleeve protectors are created for individual toes and are made from silicone, gel, or cushioned tubes.
Other protectors are more like socks for the toe section of your foot that can help to protect the area and stop any rubbing or blistering. These are more useful if it is more than one toe that is hurting in your heels or regular shoes.
These are a simple and cheap solution and often help to stop painful blisters. They are also longer lasting than a Band-Aid.
Pointed Shoes Hurt Your Toes – Buy A Toe Straightener
If you want to make pointy shoes comfortable it is important to mention that crooked or hammertoes could also be behind your problems.
Toes that are raised are obviously more likely to rub the inside of high heels or pointed-toe shoes because they are narrower than normal shoes. A toe straightening device can help to either shield that toe from friction or alternatively help to train the toe back to a normal shape.
As toe straighteners are relatively inexpensive they are a good initial way to see if you can solve the problem with the painful toe. Sometimes surgery may be required but of course, that is an extreme solution for fashion when you can wear ballet flats or regular shoes instead.
Wearing Shoe Inserts or Anti-Sliding Pads
When you wear high heels you are naturally going to find that your feet move towards the toe of your shoes. This is particularly the case if the insole of your shoe is smooth and you are wearing socks and tights that slide inside your shoe.
As your foot moves forward your toes become crammed nearer to the pointy section of the heels or shoe causing friction and foot pain.
A way to counteract this annoyance is by using shoe inserts or anti-sliding pads and placing them in your shoes to stop your feet from sliding.
These can be stuck inside your shoes, usually in the ball of foot area to prevent the problem and to cushion your feet at the same time.
Use an Anti-Blister Stick
If your shoes or high heels are just rubbing or hurting in one small area then sometimes an anti-blister stick will do the trick.
Anti-blister sticks are used to rub a creamy substance over the foot where the rubbing is occurring. This helps the foot to glide easily in the shoe instead of sticking and rubbing.
You do need to reapply the product during the day but it is a good solution if you like to wear shoes in bare feet. Plenty of people used them not just for pointy shoes but for shoes like flip-flops as well.
Obviously, this won’t work if you are wearing tights or socks with your pointed shoes.
Think About Your Shoe Material
If you want to know how to make pointy shoes comfortable you should also think about the materials that your shoes are made from.
Leather and patent shoes when they are new don’t tend to be very flexible and might take some breaking in before you can wear them. Whilst suede or man-made fabrics can feel a little more comfortable when you first put them on.
Your shoe material can make a difference to your comfort levels so think about if carefully before committing to buying a particular pair of shoes.
Choosing the Right Style of Pointed Shoes
To illustrate this look at these Stuart Weitzman Scallop Pumps. These shoes are gorgeous but the high heels have a very sharp pointed toe in a patent material which won’t have much flexibility when new. Whilst these shoes may work brilliantly on some people for others they will be uncomfortable because of the material, shoe height, and sharp triangle point.
Contrast this with these shoes from 
The key to how to make pointy shoes comfortable is to find a pair that are a little less extreme than ultra-high heels in inflexible materials. There are plenty of stylish shoes out there with more support and wider toe boxes that look just as good.
Read Related Articles
How to Stop Feet Sliding Forward in Heels
The Benefits of Wearing Comfortable Shoes
What to Apply on New Shoes To Prevent Shoe Bite
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