Back in the days when peep toe shoes were made popular, showing off a bit of skin was reserved for court shoes and sandals made to be worn on an everyday basis. But since then, the trend has been applied to such a wide variety of shoe styles, that you can easily get almost any type of footwear with an open toe.

Nonetheless, being widely available does not make peep toes appropriate for all occasions. Some workplaces will have strict rules regarding this type of footwear, and some settings will simply find this kind of footwear either too dressy or too casual. Knowing when and how to wear your favorite peep-toe pumps can save you a lot of thought, so here’s a quick overview of the options available and their best uses.

Pumps – or as they are often called court shoes, are the most classic style of footwear you can get in an open toe variation, and the easiest to pair as well. Depending on the upper and color/pattern, these shoes can go from elegant and formal – think fancy dinners or galas, to something you put on with a pair of ripped jeans on a weekend night out.

Slingbacks – shoes with an open heel area that’s covered with a supportive strap. These can go from quite formal to casual as well, but on the whole, a single item will be less versatile than a pair of pumps. If you opt for a more open style, then it’ll be a great option to wear with an evening or cocktail dress, while a more chunky one will bode better with casual outfits such as mid skirts or jeans.

Wedges – the thing everyone loves about this type of shoes is the stable and comfortable outsole that gives support to the entire foot without sacrificing heel height. If you opt for a pair of wedge shoes with an open toe, you will find that it’s an updated look that can work well for a variety of casual and semi-formal occasions. Day parties, workplace, as well as weekend outings, these will be a great choice.

Mules – with a chunky look that resembles clogs, these slip-on shoes are a great casual option for more than just one reason. First and foremost, they are supportive in the upper, being made with a generous amount of material that will cover almost the entire foot. Secondly, they are often made with a stacked heel that is much more stable than their thin counterparts.

Flats – for those who prefer to stay away from high styles, flats are a great option. Shoe designers will often offer their most popular open toe shoes in lower heel heights, which is a great choice if you require more stability, or if, for any reason, you can’t wear high heels.

Boots – last but not least, in the past couple of years, boots with open toes have become immensely popular. A fashion statement on their own; these styles are perfect for spring and autumn wear as they provide a good balance between warmth and breathability.

Furthermore, they help show off your authentic sense of fashion, and can even be combined with a huge variety of outfits, for almost any occasion.

When we think about some of the hottest and most luxurious brands in the fashion industry, ones like Prada, Gucci, Louis Vuitton, and Jimmy Choo might come to mind. A product is a promise made, but a brand is a promise kept; generation after generation. A brand and its label are a statement of quality, craftsmanship, and service found in each of its products.

When assessing the products on our list for “brand,” we took into account the quality of its products, its attention to detail and style, its reputation within the fashion industry, its commitment to customer service and its perceived luxuriousness and exclusiveness, to create an overall score for brand equity. Brand equity can loosely be defined as the pricing power a brand has in the marketplace due to each of the aforementioned factors.

So, while a product that scores high on this list may be gorgeous and exclusive, you can also bet it will much pricier, as well. After all, if everyone could afford it, it wouldn’t be exclusive or luxurious, would it? Be prepared to look amazing, but feel the pain at the bank, if a product scores high on this metric!

Because most open toe shoes come with a high heel, it’s important to consider the type of elevation you will be getting before making a purchase. If you’re buying shoes that you will have to spend a lot of time in – such as those worn at work or weddings, you need to keep in mind that comfort (or at least the lack of discomfort) should come before looks.

There’s a wide variety of heel types available in peep toe shoes. You can get completely flat shoes that will be easy to wear and will show off your nail polish, or you can get 4-inch heels that will look amazing but will require some serious skill if you want to walk around in them.

One thing you might want to look out for, especially if you want a high but stable shoe, is a wedge or stacked heel. Both of these types are chunky, which has some great benefits, even if you go with a higher height. First and foremost, seeing that stacked and wedge heels have a bigger surface of contact with the ground, they are more stable, giving you much more stability than you would get with regular heels. Secondly, they support the foot over a greater service as well, lessening the pressure that is put on the heel.

A well-chosen heel type is important for one more reason, and that's looks. Before buying a pair of shoes, especially if doing so online, you need to consider the shape of your legs. Are you more muscular? Don’t go with stilettos. They will contrast with your shape, making you appear more sturdy than you are. Or, if you’re on the more frail side, you will probably look better with a thinner heel that will aesthetically fit with your overall leg line.

Whether you are looking into buying a pair of walking or running shoes, house slippers or splurging on some peep toe heels, it’s important to get the size and shape that will fit your feet. Peep toe shoes can be a bit more difficult to find if you’re after the perfect fit, due to the front opening that greatly varies from shoe to shoe.

With closed footwear, your toes will be held in place by the front portion, which is simply not there with peep toes. If the shoes you opt for have an opening that is too large for your foot, you risk sliding forward too much and hurting yourself in the process. If you find that your toes go too far through the opening, you risk developing painful blisters, overcompensating through gripping with your toes, and even injury.

Sometimes, these issues can be corrected by wearing the right inserts. You can easily purchase silicone, suede or even leather inserts that will help grip your shoes better, or that will adjust the availability of space in your footwear. Often, these can even be used as additional cushioning, as they can help protect the ball of your foot from the shock of walking in high heels.

While peep toe shoes are fun and elegant, you need to know whether they will be appropriate at your workplace, or the function you are planning on attending. Some offices will have strict rules regarding open footwear, so before you make a costly purchase, it’s a good idea to check whether your new favorite pair of footwear will be OK to wear during business hours.

Another thing to consider with peep toe footwear is hosiery. While for a long time peep-toes were reserved for barefoot wear, the latest trends allow for much more freedom. When reaching for your peep toe pumps, you should consider the weather – if it’s autumn and kind of chilly, you can now easily pair them with some knit socks and a mid skirt, and be the most fashionable person in your group. However, if you’re wearing these shoes in the summer, you should skip pantyhose and socks and go with a barefoot look. Hate the way shoes feel on bare feet? You can purchase specialty hosiery made for wearing with open-toed shoes.

Lastly, before you decide to show off your toes, make sure that they’re well taken care of. A peep toe pump is an elegant piece of footwear, and should in no way be worn if your nail polish is chipped or, even worse, if your nails are neglected in terms of care or hygiene. Instead, wear peep toes to show off your pedicure, and to bring attention to a part of your body that’s playful and elegant at the same time.