Since the topic of this guide is the d’Orsay design, it stands to reason that all of the items listed here are going to be that, whether they come with a heel or not.

It’s hard to imagine, given how elegant and inherently sexy d’Orsay footwear is today, but it was first conceived as military footwear. The shoes were created by Alfred Guillaume Gabriel, otherwise known as Count d’Orsay, in the 19th century. The idea was to provide military men who had wider feet with more space and enable them to move around more comfortably by cutting off the sides of the shoe.

The silhouette quickly caught on in aristocratic circles and became popular not only among men but also among women of all ages. There was something alluring, bold and borderline scandalous about exposing the arch of the foot for everyone to see, and many thrived on that feeling of rebelliousness.

For your convenience, we can categorize all of the designs on our list into three groups: the everyday, the party and the formal.

The everyday designs are those such as the Toms Jutti, the Cole Haan Crissy, the Calvin Klein Ghitta. They are meant to be worn, as the name of the group suggests, every day, and in almost any occasion. They’re easy and comfortable to wear for hours on end, they are wonderfully versatile, and in them, you can seamlessly blend in at the office, at the shopping mall, and even at a relaxed cocktail affair.

Party options are those like the Jessica Simpson Claudette, the Rebecca Minkoff Brie, even the Jessica Simpson Leasia 2. They are meant to be vibrant in color, sexy in design and dazzling in the club, and in them, you should feel like you’re on top of the world. Of course, a party design doesn’t have to be a heel, as the Steve Madden Roughly also perfectly fits this category.

It is a fine line between party and formal footwear. The former should be vivacious and daring, while the later should be more elegant, and perhaps more subdued, in a way, like the Badgley Mischka Seneca II, the Calvin Klein Gella, and the Anne Klein Fabulist.

That being said, no one can or should stop you from wearing a fierce design to a formal event, or a more modest one to a party, if you so desire. Style is extremely subjective, and all that is important when you are choosing a stylish option is that it looks good to you.

The two basic shoe types we have considered in this list are heels and flats. We like to diversify as much as we can in our selections, and the topic of a d’Orsay design is not limited to only one or the other. Both of these have their advantages and disadvantages in terms of appearance and ease of wearing, as well as their comfort levels, so we are going to explore that more here and in the following, Comfort, section.

Originally popular among both men and women, today heels are mostly worn by women. They add elegance to an outfit, a poise and confidence that one might not achieve by wearing flat soled shoes. They are the ultimate special occasion footwear, though that is not to say there aren’t casual heel styles as well.

The downside to heels is that they are usually not comfortable to wear. This is arguable, of course, as different designs offer different levels of comfort, however, the consensus in the fashion industry is that heels hurt, and beauty is pain. That doesn’t always have to be the case, and make sure to read on what makes a heel comfortable in our next section.

Compared to heels, the beauty of flats is that they are an endlessly versatile design. Unlike heels, which have some limitations as to where they can be worn, flats are suitable for practically any event. A picnic out with your family? Check. A shopping trip with friends? Check. Sightseeing in a foreign country? A wedding reception? A sports game? Check, check, check.

Flats come in so many shapes and sizes that you can easily find a pair which fits your personal style and goes well with what you have in your wardrobe.

We ranked the designs in our list according to their heel heights and wearability, so that you can find an option which works for you best. If you are not a fan of heels, then choose from the top, from the several different flats that we have. On the other hand, if you are looking for something elevating, check the bottom for the highest designs in our selection.

Since we are talking about two different footwear types here, we will divide this comfort part into two: heels and flats, and we’ll discuss what makes each of them comfortable.

Let’s start with heels.

There is a straightforward rule when it comes to heel height and comfort – the lower the heel, the more comfortable it is. Heels that are around two inches in height – kitten heels – and three inches in height – classic heels – provide that all-day wearability. They might still require some practice for an absolute heel-wearing beginner, but once you get used to them, nothing can stop you from spending as long as you want in your favorite heels.

Those which are four inches and higher, however, are not as easy to wear. No matter the overall construction of the shoe, the quality of its materials or cushioning it might have – after a couple of hours in heels this high, your feet will start to hurt. If you don’t mind it, for a short period of time it won’t cause any bigger issues than pain and discomfort. However, wearing extremely high heels day after day is not a good idea, as this causes a myriad of health problems, such as hammer toes, bunions, corns and similar. Best save these heels for special occasions, particularly when you know that you won’t be spending much time on your feet.

When you’re walking on elevated soles and heels, you need all the stability you can get. This is why chunky, solid heels with a wide base are the most comfortable of choices. Think wedges, think blocky-shaped heels if you are looking for footwear you can walk around in without any problems. Wedges, in particular, evenly distribute your weight across the footbed of the shoe, taking pressure off of the ball of your foot and preventing pain in that area, as well as in the ankle and the knee.

Stiletto heels, on the other hand, while effortlessly stylish and fierce, are not so comfortable to walk on. Stability is a concern here, as well as the fact that all of your weight is pushed forward to the front of your foot. This can cause pain very quickly, and as a result, you won’t be able to spend much time in footwear like these.

While the heel height and its type are the key factors of comfort, it is important to mention padding as well. Every bit of cushioning counts, as it softens the impact of your steps, and reduces the strain on your feet and ankles. In case you’re taken by a heel which has no cushioning, however, don’t despair! There are separate gel inserts and pads you can buy and fit into your shoe for an extra dose of comfort.

In comparison to heels, flats are infinitely more comfortable. Of course, they would be, as your foot is in a more or less natural position, with no additional pressure placed on any one part of it.

However, in terms of comfort, there is one thing we need to mention – the arch support. It is not unusual for flats to have no arch support, sometimes not even cushioning in their footbeds. This doesn’t pose a big problem per se, as they are still fairly comfortable to wear, but it does mean that you shouldn’t wear them for extended periods of time. Footwear which lacks arch support is not good for our feet, as it can lead to many foot-related ailments, such as flatfoot, or even plantar fasciitis.

If you are looking for that perfect ballerina flat to wear all day long, look for a contoured footbed, and especially for an arch cookie which sits well under your foot, providing you with all the support that you need.

While style and comfort are undoubtedly important, we also have to take a quick look at the materials a design is made from. The materials are what determine many properties of a shoe, such as its breathability, durability, flexibility, slip- and skid-resistance, as well as resistance to wear and tear and so on and so forth.

Footwear made from high quality materials is always a better choice, since it performs better in almost every aspect. So what are these high quality materials, exactly?

Precisely speaking, these are genuine leather and suede. Fortunately for everyone, most of the options on our list are made from these. Genuine leathers promote a healthy foot climate inside a design and allow for good ventilation, they are durable, and they also have that wonderful ability to change shape over time, and conform to the outline of your foot, providing unparalleled comfort.

The only downsides to genuine leathers are that they are expensive - more so than the synthetic options - and they are, clearly, not animal-friendly.

If you are looking for a low cost option, or for a vegan design, then something made from faux leather, such as the Steve Madden Roughly or the Rebecca Minkoff Brie (though the low cost part is debatable on the latter one), are the go-to styles.

Keep in mind, however, that synthetic leathers are not nearly as good as natural ones. They are not as breathable, and tend to be stiff and rigid, meaning that they are likely to cause you blisters. They are also not as durable.

In the end, which option you go for doesn’t have to be based solely on the quality of its materials. Of course that this is useful information to know, and it might help you make a better decision, but you shouldn’t worry about it too much. If the design looks good to you and is comfortable to wear - that’s what really matters!

A final factor that you should take into account before settling on an option is its durability. How long will it last? Will it be worth the cost? How much can you wear it before it gets damaged beyond repair and you have to buy a new pair of shoes?

All of these questions have one simple answer: it depends. It depends on the quality of the materials, the quality of the construction, how often you wear the design and in what conditions, how well you maintain it and similar.

We have already mentioned how genuine leathers are exceptional in quality, and the same is true for their durability as well. Especially if they are layered thickly, they can even outlive a rubber design!

In contrast, synthetic leather is not so long-lasting, and tends to flake and crease and ultimately fall apart sooner rather than later. There is nothing you can do about that, we’re afraid, as it is the nature of the material.

It is also important to emphasize that the designs which you wear only occasionally will clearly outlive the ones you wear often, or even every day. No matter how high in quality, a shoe will start showing signs of wear and tear eventually, and it will happen relatively quickly if it is often used.

Now, this isn’t us saying that you should wear your new fancy footwear less often. Quite the contrary, this is just us reminding you of this fact, so that when you do wear your shoes everywhere you like, you’re not surprised that they get a scuff mark here and there.

We are always in favor of wearing the heck out of your favorite shoes and being happy and confident in them, than letting them collect dust in your wardrobe out of some arbitrary fear that something will happen to them. Shoes are meant to be worn, and something will happen to them, but you will also get seasons and seasons of being stylish and comfy before that happens!