The Complete Guide on How to Buy & Wear High Heels

High-heels: A Brief History

High heels have been around for centuries. But not in the form we know them today. In 3500 B.C Egypt men wearing high heels was the usual run-of-the-mill sight. Used by riders, by actors or for special ceremonies, high heels were a statement of power and status. Fast forward 6 millennia, to an era where high heels have lost both their practicality and their powers as social statements. 

Fashionable high-heel shoes

We’ve turned heels into devices to redeem our self-confidence, lengthen our silhouettes, and feel sexy.

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Most petite framed ladies out there rely on high heels not only for special occasions, but for daily wear, to the detriment of sore toes and aching backs. Most of the drawbacks of wearing high heels could be averted with some education on your foot type and what kinds of heels and size suit your foot. Read on, for essential tips on how to choose the appropriate footwear, how to buy high heels online and what occasions call for red high heels.

silk shoes 1760

A pair of silk shoes over goatskin, dating from the 1760s.

The step sister or Cinderella?

The entire idea behind wearing high heel shoes is to feel empowered and remember to keep your chin up and your shoulders back. With these in mind, you don’t want to feel like the step sister of Cinderella, but like Cinderella herself. Most women will think their shoe size remains the same throughout the years, but that’s not necessarily true. With our bodies constantly changing under the influence of other factors, our feet too are prone to swell up and make our shoe size go up by half or even a whole size. Make a mental note to measure your feet once a year to make sure you buy the right foot wear. High heels look incredible, but they don’t have to painstakingly hurt your feet. With that in mind, follow the next chart to choose a comfy fit:

  • 2 to 3,5 inch heels require half a size larger shoes;
  • 4 to 6 inch heels require a full size larger shoes;
  • 6 inch heels and everything over that length require one and a half larger shoes.

The reason behind this trick is that feet naturally swell up during the day because of walking and even standing up. Add high, uncomfortable heels to this lethal equation and you’re in for some blisters and bunions. But if you go a size up when you choose a stylish pair of high heel boots, your feet will be left with ample room to swell up and you’ll be more comfortable during the day. If you feel you’ve chosen a size that is too large and your high heel sandals tend to slip out of your foot when you’re walking fast, you’ll find a quick remedy in over the counter gel insoles for high heels.

louboutin high heels

A pair of high heeled Louboutins

Thin soles and thin heels are a no-no

Train your brain to automatically look for chunky heels and platform soles whenever you step into a shop and you’ll be forever grateful. I’m all for looking sexy and confident and I can say a wobble is far from appealing. Pencil thin heels like stilettoes are hot and look great with the occasional LBD. 

Jennifer Lawrence falling

Remember: thin soles and thin heels can be a girl's best ally or her worst nightmare. This is just one of Jennifer Lawrence's falls. Mind you, she was wearing thin heels for both occasions.

If you’re heading to an event where you only have to step out of the car, say hello to a couple of friends and sit down for the rest of the night, you might pull off thin heels and a paper thin sole. But if you’re in for a whole night on the dance floor, or if you want to run errands and still turn heads, thick heels or platforms are your new BFFs. Not only will you feel more comfortable, you also won’t wobble or risk taking a tumble when you’re going down a few stairs. Leave the strappy sandals that would probably cut into your ankles on their shelves and head for platforms that will relieve the pressure and keep you on your feet the whole day (and night).

jennifer lawrence fall on red carpet

This is the second fall, shoes and all.

Less is not always more

It’s super cute to display your gel pedi in the summer, but don’t choose shoes that have little top coverage, unless you want to endure the pain. The principle is quite simple: the less material you see in a shoe, the less comfortable it’s bound to be. Ever wondered why your winter high heel booties feel so comfortable? It’s not all up to the high heel or thin sole to make it painful. Additional support such as a thick ankle strap will keep your foot locked in place, avoiding friction, pressure and pain at the same time.

beige stilettos

Pencil thin stilettos.

Let’s talk heels!

High heels complete an outfit like no other accessory or clothing item. But they’re not always your unconditional friends. Heels that are too small can actually make you look short and stocky, while a pair of sling back heels are not appropriate for all events. Browsing, trying out, buying and wearing high heels is no easy task. And although they do say practice makes perfect, who wants to experiment with all types of high heels just to find the perfect fit?

Fortunately, there’s a quicker way to root out a potential faux-pas and replace it with the correct fashion choice for any event, foot type and outfit. The following list will give you some insight into what you should be paying attention to when buying a pair of high heels and what suits your body type.

1. Kitten heels

Valentino studded kitten heels

Valentino studded kitten heels

With a narrow range between 1.5 inches (3.5 centimeters) and 1.75 inches (4.75 centimeters) kitten heels are irreversibly associated with Audrey Hepburn. It’s easy to guess who can benefit from wearing kitten heels just by thinking of Hepburn. She was tall (5' 7"), slender and didn’t need any help with lengthening her figure. When she wasn’t wearing flats, she used to choose kitten heels, which were comfortable, yet stylish and versatile. Worried you don’t know how to wear high heels? Nowadays, kitten heels are dubbed “trainer heels”, since they are perceived to be the best first pair of heels for any young lady. However, easy to walk in and elegant, kitten heels are not only suitable for the younger generation. 

kitten heels in different styles

Feminine and delicate, they’re also the perfect ally for office outfits and they can be worn all year round with anything from cropped pants to pencil skirts. After proving they can be both chic and practical, kitten heels made countless appearances on the catwalk under famous signatures such as Jimmy Choo and Christian Louboutin. What to keep in mind when investing in a pair of kitten heels? Take your time and look for a feminine shape, steering away from chunky heels. A pair of closed-toes made out of black suede will look stunning with skinny pants in the winter. If you’re shopping for spring or summer, opt for an open-toe pair of kitten heels that has an ankle strap.

2. Cone heels

cone heels on suede sandals

Cone heels black suede sandals

With a self-explanatory name, cone heels are wider at the sole and slimmer at the base. This heel can have different heights, ranging from 1.5 inches (3.5 centimeters) to 6 inches (15.25 centimeters). They are found both in shoes sand sandals, with or without a connected platform. With an upside down triangle or ice cone form, these heels also vary in thickness and can range from pencil thin heels to thick, round cones. Cone heels have a few subcategories:

Horn Heels

Claw Heels​

Banana Heels

high heel shoes

Three styles of heel, from left to right: horn heel, claw heel, banana heel.

They have a futuristic, edgy feel to them. They are curved and resemble the letter C.

They ​ are the subtler version of horn heels and they are only slightly curved.

They are wider starting at the sole and only slightly slimmer where they touch the ground.

If you don’t have slim calves, cone heels are the best choice for you. Hourglass silhouettes with generous hip lines are beautifully complemented by cone heels, which add a touch of toughness. A rounded toe suits a large bust and balances out any outfit.

3. Stiletto heels

black stiletto shoes

Black stilettos with skinny jeans

We’re all familiar with this kind of heels because we all own at least a pair of stilettos. And this is not because they’re the epitome of comfy and versatile shoes, but because they’re striking and ooze sex-appeal. Most often found in closed-toed pumps or boots, stiletto heels are worn at work, on business meetings, at weddings and parties. They suit slimmer figures and they’re a must-have among petite framed gals. Stilettos make a terrific job of giving the impression the wearer is thinner, accentuating the legs, especially the calves and enhancing confidence. Stilettos make the wearers so appealing because their posture is completely altered: the calves flex, while the bust is more prominent. Undoubtedly a show stopper, the stiletto heel best suits short skirts and dresses, as well as cropped pants. The length of a pair of stiletto heels ranges widely. They usually start at around 2 inches (5 centimeters) and can go up to 10 inches (25 centimeters) when the shoe comprises a platform.

4. Pumps

blue suede pumps

Cute blue suede pumps

A staple in any woman’s wardrobe, a pair of black, classic pumps will instantly boost any outfit, whether we’re talking about ripped jeans or cocktail dresses. Similarly to stilettoes, a nice pair of pumps will slim down any silhouette, creating the illusion of longer, more toned legs. Because the heel length varies and there is a slew of styles to choose from out there, pumps have become versatile and suitable for most body figures. There’s a simple test you need to keep in mind when you’re on the lookout for the pumps of your dreams. If your calves are on the muscular side, you’ll want to go for a chunky pair of pumps with a hidden platform that will suit your legs and ankles. On the other hand, if your legs are long and slim, choose a pair of shoes that look delicate and have a thin heel. What about the length of the heel? It all boils down to personal preferences and your endurance level. If you’re a seasoned high heel wearer, nothing’s stopping you to go bold with an 8-inch pair of pumps. If your style is better defined by dainty and pretty, stick around the 4 to 5 inch area. This will give you a stylish look and won’t overwhelm your outfit. Black high heels look good with mostly anything: dressy casual, office or glam, it’s up to you how you style and wear your pumps.

5. Wedge heels

cute platform wedges

Platform wedges

The partner in crime for novices and a familiar face for high heel veterans, wedges are extremely popular and well-loved by everyone. We don’t have to look too far for the explanation. Wedges are found in boots, sandals and shoes, from casual footwear to edgy or classic styles. Effortless to style, unpretentious about body figures, wedges do a great job at distributing the entire weight throughout the sole, conveying a slimmed leg and flattering the whole figure. Platforms with narrow wedges are ideal for short ladies, while thick, chunkier wedges suit fuller silhouettes, like hourglass or pear body shapes. Wedges are very permissive and can be worn all year round with anything from LBDs, maxi dresses, jeans, pantsuits or shorts. Whatever style you go for, make sure you keep an eye out for proportions and don’t forget about balance. What does this imply, specifically? You want to create a flowing, homogenous outfit in order to achieve the appearance of a taller body figure. To do this, pair a chunky pair of wedges with softer materials for a fluid silhouette. A subtler, more neutral wedge makes for a more lenient footwear choice. This can be paired with bright, bold patterns, without risking looking too busy.

6. Prism heels

prism heels edgy design

Prism heels with an edgy design

Prism heels comprise of a triangle made of their three sides. They’re usually bold and loud, created to be noticed and to complement minimalistic outfits. Prism heels vary in length and thickness, which makes them easy to adapt to sundry body shapes. They offer stability and they are very comfortable, especially when they are paired with a stable hidden platform. Unpretentious, prism heels can easily be dressed down or dressed up and they look beautiful next to jeans, tailored pants, maxi dresses and shorts. Found in sandals, shoes and boots, the prism heels have a singular charm about them and they are reminiscent of the 60s. In addition to being chic and elegant, they’re also suitable for new high heel wearers. They are comfortable and stable, which makes them ideal for a lot of walking around. If you’re looking for a pair of boots made for walking, but you don’t want to sacrifice heel length, opt for a pair of prism heeled booties that will keep your feet warm and elongate your frame.

7. Spool heels

navy suede heeled boots

Blue suede spool heeled boots

Not the first choice for contemporary fashionistas, spool heels sport an hourglass silhouette that is wider at the top and narrow in the middle, only to flare out again towards the bottom. Evoking Baroque nostalgia, this type of heels occasionally pops up in random fashion collections, integrated in sandals, boots or peep-toed shoes. Spool heels start at 1 inch (2.5 centimeters) and can go up to 4 inches (10 centimeters). They are extremely comfortable to walk in and they are also known as Louis heels or French heels, since they have their roots in the vintage style of 1600s France. Smooth, rounded and with a triangular shape at the bottom, spool heels are often dismissed as dated. However, fashion enthusiasts who incorporate spool heels into their outfits can’t praise them enough for their comfy fit and classy feel, especially when they are paired with a hidden platform.

8. Sling back heels

tan colored mutiple strap sandals with sling back heels

Tan sling back sandals

With a strap around the heel or ankle, sling backs are comfortable and sexy, particularly if they’re on the taller side. Sling back heels are seen in sandals and open or closed shoes. The strap varies from chunky buckles to adjustable and elastic bands. Great staples for hot summer months, sling back heels are easy to put on, easy to slip off and, provided you have the right fit, they’re incredibly comfy. The wide range of styles and designs doesn’t disappoint and caters for all needs: from formal sling backs that excellently complement a pantsuit to smart casual sling backs, which can be paired with loose trousers or a loose top. Not to mention evening wear, another field where sling backs excel: perfect companions for little black dresses, a sparkly pair of sling back heels will add enough spice to a sophisticated outfit. Regardless if we’re talking about sandals or shoes that sport a sling back heel, they were designed to be put on display and they’re always ready to steal the show. With this in mind, don’t hide your sling backs behind flared jeans, but rather show them off with mini and demi skirts or cropped and short pants. You might also want to steer away from socks. If the weather doesn’t allow you to sport your favorite sling backs, you’re better off leaving them at home and choosing other footwear rather than accessorizing them with socks.

9. Platform heels

black Chunky platforms with laces

Chunky platforms with laces

I'm not exaggerating when I’m saying platforms are super stylish and daring. This is one of the reasons why they’re not the easiest shoes to wear. However, the length and slimming effect they add to your legs makes them irresistible. This might come as a surprise to many, but platforms have nothing to do with the style, thickness or length of the shoe’s heel. Instead, platforms refer to the part of the sole that rests under your toes. Did we mention they’re comfy and you practically feel like you’re wearing flats? Nothing says street style as well as platforms. If you’re not afraid to stand out and turn heads, you can rock this kind of heels no matter what your body frame is. Platforms show up in sandals, shoes and boots. But the latter are, by far, the most beautiful looking ones. Get a pair of platform booties and you’ve got yourself the best footwear for skirts, maxi dresses, ripped jeans, cropped pants and loose joggers. An all-time favorite for petite ladies, platforms instantly add the much sought after length and make your calves look like you’ve been hitting the gym five times a week. Cute or edgy, romantic or grungy, platforms seem to tick all the needed criteria for fashion enthusiasts. Check out these types of platform heels for more inspiration:

Platform Boots

Flatform Shoes

Platform Sandals

Heelless Platform

platform shoes

Classic type of boot, but with a thick sole and heel. The key words here are tall and daring.

A modern take on platform shoes, with the height of the sole remaining the same from heel to toe. Needless to say, they are very comfortable.

They never go out of style and they're a summertime staple, since they combine a comfy fit with a chic design.

Often associated with Lady Gaga's bold style. The most recent addition to the bunch, heelless platforms remain a statement piece, only to be worn for special occasions.

10. High heel sandals

Silver and gold high heel sandals

Silver and gold high heel sandals with mustard lower.

The ultimate trendsetter for summer and parties, high heel sandals are the least comfortable type of heels. However, they make up for the discomfort with a striking, sexy design that is a must for any strapless dress or slinky playsuit. Designers prove that they have no shortage of ideas with each new season, to the delight of fashionistas all around the globe. This translates to gladiator sandals, lace up high heels, tasseled sandals and even transparent plastic high heel sandals. Despite the fact that they’re most likely bound to become uncomfortable after an hour or two (in an optimistic scenario), high heel sandals are generous in their design and suit most body frames. For petite gals with slim legs, pencil thin heels are the way to go. However, curvy body shapes are better suited with chunky heels and tougher materials. These sexy high heels are flashy enough on their own, so they’re best paired with longer skirts or pants that reveal the ankles. Combining a miniskirt with a pair of high heel sandals might look a bit too tacky.

3 Things to Consider Before Buying Heels

platform high heels black suede and bow

Cute platform high heels with bow detail

Cute, right? But how tall should you go? And what's the best way to select a heeled shoe size? And, of course, how do you make sure they're not going to be killing your feet?

Click each tab below, for detailed answers to all your high-heel buying questions!

  • Height
  • size
  • test drive
several pairs of women's legs in high heeled shoes

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It’s not worth denying it: we like to go big when it comes to high heels. But maybe that shouldn’t be your sole worry when you’re choosing a pair of high heels. Rather than plunging into an adventure involving bunions, blisters and a wobble, insecure walk, you’re better off knowing your limits. Taking this into account, don’t head straight to the 10 inchers if you’re shopping for your first pair of heels ever. The wisest way to get started is to ease your way into it either by investing in a pair of high quality kitten heels or by choosing a pair of trustworthy wedges. Give your feet time to adjust to the new shape of the sole. Start by wearing them in your house for 15-30 minutes at a time and see how your feet react.

Breaking in a new pair of high heels

It happens to the best of us: we got a pair of drop-dead-gorgeous high heels that don’t seem to really fit us anymore when we get home. Wondering how to wear high heels comfortably? You can try enlarging the shoes yourself, at home. If you’re ready for a DIY little project, all you’ll need is a couple of zip lock bags, some water and a freezer. Fill up the bags with water and insert them into your shoes, making sure to push them enough so that they fill in the toe box. Put them into your freezer and leave them in there until the bags freeze (at least 3 hours). The water in the bags will expand, putting pressure on your shoes and forcing them to slightly enlarge. When you take them out, wipe them with a paper towel and allow them to reach room temperature before trying them on. They should feel looser, just like a pair of heels you’ve worn for years. You can repeat the procedure several times, until the high heels feel comfortable enough to walk in.

barely there black sling back shoes

Classic black sling backs

Image sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15.

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