Whether this is your first or twentieth pair of high heels, fit needs to be your main focus when deciding which pair to get. Even if you are a high heel pro, unless you consistently buy the same style from the same brand, chances are they are not always going to fit the same way, and you probably will not be the same size in every brand.

The first step to buying your new pair of heels is knowing your exact size. Take the time to measure your feet, and then based on the brand know whether or not you will need to size up, down or stay true to size. Brands are all different, some offer different width sizes for wider feet, which is great for those with larger feet that have a hard time finding their size. If you have wide feet and the brand you’re looking at does not offer different width options, always size up ½ to a full size.

The amount you will need to either size up or down not only depends on the brand but shoe style as well. You want to find a shoe that has enough space to properly accommodate your feet and toes. Even though you may love the look of a certain style, if it just doesn’t work for your foot shape and size, it is not worth buying and then suffering through pain while wearing. The three most popular toe shapes in high heels are:

Pointed Toe – Get the appearance of longer legs while looking sleek, and sophisticated. Not a good option for wide feet, as they may cause toes to feel cramped. Perfect heel for work or business events.

Round Toe – Great for making feet look smaller, as no length is added on to the toe area. These also have much more room in the toe box which is very accommodating for wide feet. Depending on the style, these are a better style for going out and not the workplace.

Open Toe – The perfect choice for warmer months, but can cramp toes if the fit is not right. Keep in mind your toes are exposed so a pedicure may be needed prior to wearing. These are the best option in the summer.

Unlike running shoes or most sneakers, high heels will need to be broken in, and that is not always the most fun or comfortable process. Breaking in your new heels may happen quickly, or could take quite a bit of time, and this all depends on the style, heel height, and material.

Leather or suede is always the best option when not only looking for long-lasting quality shoes but ones that will fit best the quickest. These materials are much more flexible than say a synthetic fabric and therefore will mold to your feet much faster. Depending on the type of leather and its stiffness, after a few wears, you should notice the leather sort to almost soften and the shoe feels much fitted to your foot without any sort of irritations occurring.

The fit is very important when buying high heels and fit plus size varies from brand to brand. Therefore, it’s important to know your shoe size and how each brand constructs the fit of their shoes. For wider feet, you might have to go ½ or one-size up.

Shoe style plays an important role in shoe fitting. Some styles are more accommodating than others and if a certain style brings pain to your feet, they are not worth it. Pointed, rounded and open-toe are the most common styles.

High heels have to be broken in and that can be short or long depending on various factors such as heel height, material, and style. The material is usually the best determining factor in fit. Leather and suede will break-in and mold to your feet the quickest and synthetics can take longer. Natural materials can be more durable too.

When it comes to high heels, quality can be quite important and be the difference between owning a pair of shoes that not only feel great but look great as well. There are many details and features that come into play when picking out the perfect pair of heels and although they may not all seem important, they will make a difference long term.

A trendy or seasonal item can be fun however they are not shoes you should invest in because they generally are not something you will reach for very often. As the seasons change you will start reaching for other shoes, and slowly your heeled sandals will be pushed further and further back into your closet. Always think about the amount of use you will get from the shoes, and if by next season, or year they will be something you will want to wear.

The first thing you will notice when looking at and trying on high heels is the material of which they are made. They will either be leather, suede or a man-made, synthetic material, and it is important to pick the right one for you. If you are looking to splurge, and invest in a pair of heels opt for higher-end brands and fabrics that you know will never go out of style, and not fall apart after a few wears.

Leather is the most classic material and is timeless, so you can be certain that regardless of the season, or place you are going, a pair of leather pumps will add to any outfit and look sophisticated. It is also a relatively easy material to care for and keep clean. If you wish to not wear animal byproducts, there are plenty of designers creating beautiful vegan leather shoes that are of the same high quality.

Price is an easy way to determine whether or not a shoe is genuine leather or suede, however, if you are still uncertain, the inside of the heel will either state “man-made upper” or “leather or suede upper”. If you wish to wear this long-term, or as an everyday type of work shoe do not purchase a synthetic material, however for short-term wear, or to simply wear once to a special event, this is fine.

The sole is also very important, especially the way it is put into the shoe. If it is glued in it has a higher chance of lifting sooner and is a sign that they are not expensive quality. Sewn insoles last much longer and look more seamless. The insole lining should be made of leather and be throughout the shoe, not just on the insole. This not only is great for comfort, and preventing irritation but leather is a very breathable material and will allow your feet to breathe throughout the day not feel clammy and hot.

Quality determines how high heels look and feel and many details can determine quality. Focus on the material (leather, suede, synthetic); its construction and style. Trendy shoes only last a season and synthetic shoes sometimes last only a few years.

Take a look at the soles. Glued on soles can be a sign of cheap quality but sewn-in is usually a sign of top quality. The insole should be looked at too. If the insole is leather, you have a quality heel, and it’s even better when the leather is throughout the heel.

Your high heels will not instantly feel comfortable the second you slip them on, there will be a break in period, however, look past needing to break them in and think about the long-term comfort. The height of the heel, if any part of it rubs against your ankle or foot in a bothersome way, and where you plan on potentially wearing them.

You will know fairly quickly the comfort level of your new heels and whether or not they will be best suited for your workplace, events, or one-time wear. If you are looking for a heel to wear for hours on end and plan on being on your feet you need to choose a style that will ensure stability. Stability and comfort go hand in hand and you may look past small features, but these can make all the difference.

Straps – Ankle straps, gladiator style, slingbacks and any other style that is adjustable and can be secured will add support. Your foot should not be sliding around in your shoe as this will make it harder for you to walk and can cause your ankle to roll which may lead to injury.

Thick Heels – The thicker the heel, think wedges, for instance, the more stable you will be on your feet, and the higher you can go without being wobbly.

Platform – This added bit of height to the front of the shoe can make a large difference when it comes to high heels being comfortable and easy to walk in. The higher the heel, the more platform it should have. Otherwise, your foot will sit at a very uncomfortable angle.

When deciding which heel height is best for different events and day to day wear there are a few general rules of thumb. However, it’s good to always trust your style and go off what feels best for you. The most simple, and easiest to wear is the kitten heel, this is usually under 2” and should be comfortable for long hours at a time. The most common heel for work and any other business or everyday event is 3 inches, and this is usually the average height on a pair of pumps. When you start getting in 4” and up you will notice most of these shoes have platforms as well and are best suited for evening events, dinners, and will not be the easiest to walk around in.

The first time you slip on your shoes you should notice how much cushioning they either have or lack, and this will determine whether or not they are worth getting. High heels are not known for their immense cushioning and plush insoles because unlike running shoes they are not meant to be walked in for long periods. However, they should have at least a small amount of padding in the front of the shoe, where the ball of your foot sits because this is where the most pressure is applied due to the angle your foot is on.

If you plan on wearing them for longer than you feel they’ll be comfortable for, insoles can usually always be added in to help with cushioning, however, ensure that with these added in there is still plenty of room for your feet, and the shoes do not fit too tightly now. If your heels are too tight, the first place you will notice it is in your toes. Depending on the material it may potentially loosen and stretch slightly, so if they are ever so slightly too tight that may be ok. Squeezing your toes and causing immense discomfort though will not get better with wear and time.

On first wear, high heels can be uncomfortable, especially during the break-in period, but do not give up on them too quickly; give it time. However, if the discomfort comes from rubbing or too much pressure from the heel, you might want to pass the particular heels on.

Take note of how and where you are planning to wear your heels. Longer hours or lots of activity require a heel that offers stability and cushioning. Certain heels fit best in certain environments so those party heels might not hold up in the office.

Don’t forget style and height too. Thin and lightweight heels might not provide much in comfort but heels that have ankle straps, platforms, and thick heels can. The heel height will determine the comfort.

Remember, the higher the heel, the more pressure on your feet. 2’’ and lower is best for longer wear, 3” is best for work, and 4” or more is best for occasional and special wear.

Lastly, there should be cushion padding in the ball and heel of the shoes as most foot pressure accumulates there. For additional comfort, you can add insoles but make sure they aren’t so thick that your heels become too tight to wear.

It may seem like common sense; however, one of the most important criteria that we utilized to develop this list was the type of heel. You'll notice that there are a few different types of heels on our list. The heel type helps to determine the comfort, use, and often occasion you'll wear the shoe.

Types of Heels include:

The last piece of criteria that we want to discuss is relating to the relationship of the price tag to the value that the footwear offers. Now, as consumers, the goal is to purchase a product that offers either equal value to the price tag, or more value. However, given the culture that we live in today, more people have become accustomed to, and okay with, purchasing products at a much higher price tag and much lower value.

We assessed each product on the criteria above and compared the value to the median price point. We focused on answering the following questions: