Heels Check

Heels Check
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High heels aren’t just a type of shoe. For many, the popular shoe style is a way to channel femininity, power, and even sexiness. Needless to say, there’s an undeniable allure when it comes to the feelings associated with heels. It only makes sense that the popularity of women’s heels transcends decades, from the kitten heels of the ’50s to the platforms of the ’70s to the strappy heels of the ’90s. High heels have history—and some serious staying power.
In the 2020s, heels are still a cornerstone of the shoe market, from noughties-inspired styles to classic black pumps. But navigating the seemingly endless options of high heels can be difficult for those not well versed in shoe verbiage. After all, a “D’Orsay” sounds like a French pastry and “kitten heels” sound like a questionable addition to your furry friend’s paws.
To help you decode high heel taxonomy and make shopping that much sweeter, check out the guide below for all you need to know about women’s heels —including how to make them actually comfortable.
When shopping for the perfect pair of heels, it’s helpful to know what type of heel structure you’re looking to buy. Whether you decide on soaring stilettos, beginner-friendly wedges, or anything in between, knowing a bit of heel anatomy is undeniably important. Heels can adhere strictly to these broad categories or mix styles for a heel structure that’s out-of-the-box. But getting familiar with the below options is a good place to start before scrolling through countless shoe options.
First introduced in the 1950s, stiletto heels feature long, thin heels—often several inches in height—like this Jimmy Choo pair . This type of heel is actually named after the stiletto dagger, so it’s no wonder the style is synonymous with fierce and edgy femininity—not to mention seduction.
Continental heels are a type of stiletto that feature a curved backline and a straight front, like these branded Balenciaga heels . Pumps, a classic heel style, often feature a continental heel.`
Popularized in the 1950s, the kitten heel is also a type of stiletto, only significantly less intimidating. A kitten heel is only about one to two inches high, making walking on them very easy, even with the technical stiletto classification. Kitten heels were first created as “training heels” for young girls but became popular with women of all ages for their comfortable yet formal style. Today, kitten heels are sought out for their vintage feel, like this Coach pair .
A great introduction to heels with height, wedge heels include a “wedge-shaped” piece that lifts the heel but provides a flat surface to walk on, like these STAUD stunners . Wedges are known for being incredibly stable, providing the same height as tall heels with more forgiveness when it comes to balance, thanks to the flat, sturdy sole.
A tapered heel features a large, stable surface area at the top of the heel, but slims to a thinner point at the bottom, like these unique Gianvito Rossi glitter heels . Also known as a cone heel, this heel shape is significantly more advanced than wedges, but still provides a good amount of stability for those working up to a stiletto heel.
A block heel is just what it sounds like: a girthy square-shaped heel that provides a lot of stability for the wearer. Block heels can be short, super-tall, or anywhere in between. They are versatile and typically easy to walk in, like these Kate Spade booties .
A flared heel starts out thinner at the top of the heel, then curves to a wider base where the heel connects to the floor. This heel style provides more stability than many types of heels, thanks to the broad base. These bold Stella McCartney glitter boots feature a flared heel that makes all that height less intimidating.
A type of flared heel, a spool heel has somewhat of an hourglass shape, flaring at the top of the heel and then slimming out in the middle and then flaring at the bottom yet again. The name comes from the heel’s resemblance to a spool of thread or cotton, demonstrated by this golden Vince Camuto shoe.
One of the most important things to consider when shopping for a high heel shoe is heel height. If you are new to the shoe style, it’s best to stick to proverbial training wheels with a pair under 2 inches. If you’re a seasoned pro who happens to be going to an event where you’ll be sitting all night, then tossing on a pair of 5-inch heels won’t even make you bat an eye. To assist you in all of that decision-making, check out this breakdown of heel heights.
Kitten heels and short block sandals fall into this category, giving you a touch of height with virtually no discomfort. Heels clocking in at 2-inches and under are the top choice for beginners, lifting your heel just enough to adjust your walk and ease you into the shoe style.
Commonly known as “pumps,” 3-inch heels are some of the most common heels on the market. They are perfect for the office or events where you’ll be on your feet a bit. Yes, they are more advanced than kitten heels. But pumps are still friendly for most people, even if your balance could use a little improvement.
Once you get comfortable in your pumps, graduating to 4-inch heels is the next step. Platforms, wedges, and other chunky heel styles are especially popular in this category, giving you the height with some added stability. But you can easily find a killer pair of 4-inch stilettos out there if you’re feeling daring and confident in your skill.
If you’re a pro who could balance on a pencil, this heel height is for you. Even 5-inch wedges are a challenge to walk in—and that’s not to mention the trouble of towering stilettos. If you are choosing a fantastically high heel, make sure you’re a balancing pro—and that you don’t need to stand much throughout the night.
Let’s cut to the chase: The trick to making heels comfortable is a good fit. Period.
If your foot slides around or your heel is “bobbing” significantly in the shoe, it’s too big—even if it’s your usual size. If you feel any pinching or have overhanging toes, your heel is too small—and blisters are in your future. The perfect heel will be secure, but not tight. Your heel will fit perfectly in the designated area of the shoe, and your toes won’t smash uncomfortably when you step. Sure, you may feel some discomfort due to the inevitable arch of your sole and pressure from standing on the ball of your foot. But that feeling shouldn’t be immediate and should disappear quickly after taking off your shoes for the night.
If you already own heels that are too loose or have “hot spots” (a.k.a. points of pressure leading to discomfort and pain), try shoe inserts and pads to add additional cushion. It’s a cheap fix, especially when dealing with designer duds.
Finding a good-fitting shoe is half the battle when it comes to walking in heels. The other half is practicing a simple walking technique that’s unique to this classification of footwear. Many heel-wearing experts advise walking heel to toe in high heels, finding your stability on the heel of the shoe then pressing down to the ball of your foot where there’s more surface area. This also cuts down on the tell-tale “clunk” of heavy feet, adding more polish (and less noise) to your stride.
Heels also require a shorter stride than a flat shoe, so be sure to take baby steps, keeping your walk slow and steady. When taking those short, slow steps (heel to toe, remember?) put one foot in front of the other—literally. Imagine you are walking a tightrope, walking in as straight of a line as possible. It takes some practice, but soon, these essential tips will just become second nature rather than an overwhelming checklist in your mind.
A bonus tip: Be sure your heels have good traction to help any slips and slides on slick floors. If your heels need a little help, scuff the bottoms on a sidewalk or grind the soles with sandpaper to break them in a little. There are also specially made shoe pads on the market if you’ve picked up a particularly slippery pair.
All shoes have different toe shapes—and that certainly includes heels. From pointed-toe pumps to open-toe sandals, a heel can completely change depending on the toe shape. Check out the nude heels below to learn more about the most common toe shapes you’ll see when shopping for heels.
Rounded toe heels are ideal for those with wide-width feet, giving your toes more room to splay naturally, like these Nine West round toe pumps.
A pointed-toe pump is one of the most noted heel shapes—and a classic. The shape is ideal for those narrow feet, like this nude pair of Christian Louboutins .
Like Goldilock’s porridge, almond-shaped heels—like this Rebecca Allen pair —are the perfect in-between shape for any foot shape. Whether you have wide feet, narrow feet, or in-between feet, an almond shape will fit like a glove.
An incredibly modern style, a square toe box is wide-foot friendly—but works with all foot shapes. You’ll often see square toes on mules, like this pair of Marc Fisher stacked heel shoes, or heeled sandals.
A peep-toe shoe, like these Chinese Laundry platforms , shows off a few of your toes—most notably your big toe and second toe.
An open-toe shoe is similar to a peep-toe shoe, but shows all of your toes, like these Steve Madden platforms . Be sure your pedicure is in check before busting these out.
Heels can, of course, be combined with several different types of shoes, from heeled loafers to heeled sandals to heeled Mary Janes . But the terms below are relatively isolated to heels, describing common silhouettes of the popular shoes.
Pumps are arguably the most common high heels you’ll find on the market. Pumps, like this Saint Laurant pair , often feature 3-inch heels and have a closed toe, most often pointed or rounded.
A stacked heel appears to feature stacked wood or leather to make up the layered heel, like this Madewell pair .
Synonymous with the ’70s, platforms are chunky heels that feature a dramatically raised sole, like these Jeffrey Campbell heels . They often feature a high block heel, adding several inches to your height. But the towering shoes are somewhat of an optical illusion. They are easier to walk in than they appear, as the raised sole helps compensate for the intimidating heel.
Slingback heels have an open back with a strap around the heel, like this mint Zara pair. Many slingbacks feature a buckle or elastic to keep the strap snug, tailoring the fit to your foot.
An ankle strap heel, like this Steven Madden pair , features—you guessed it—an ankle strap for extra security around the heel. They differ from slingbacks in that the strap encircles the ankle rather than securing the shoe just at the back of the heel.
T-strap heels most often feature a closed toe and an ankle strap, which are connected by a midline strap. The design is synonymous with vintage vibes, like this Clark’s pair.
D’Orsay heels—which are most often pumps—feature large cutouts on the inside or both sides of the shoe, revealing the arch of the foot, like this pair of Louboutins . It’s an even sexier take on the heel, as if that was even possible.
A mule has an open back, like this Nine West pair . Mules can feature any type of heel, from a high stiletto to a wedge to a kitten heel. They can even be flats, though that’s less common than a heeled version.
Known as the quintessential summer heel, espadrille wedges feature a rope heel and, most often, a canvas or fabric upper, like these Jimmy Choo wedges .

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We know the pain of uncomfortable heels all too well.
Maybe it started at 15 when you were walking into the school gym wearing your prom dress . Or maybe you first experienced the agony when you wore a sun dress and those strappy heels on a first date.
Whenever your introduction to the painful world of heels was, it may have made you forever fearful of any shoe over one inch tall.
But fear not, because beauty isn’t pain. You can still look fabulous without ending the day with sores, welts and red toes.
Introducing, the comfiest heels you’ll ever own.
Curated from top brands such as Cole Haan and Everlane , you’ll find a list of the most comfortable women’s heels for work, weddings, commutes and more. Simply browse the below options to find your perfect sole mate.
Available in black and Amphora leather options, the Cole Haan Grand Ambition Pump is the comfiest of the comfiest.
It’s elegant silhouette is constructed “embracing the contours of your body” to create the perfect fit. The shoe also features responsive cushioning that adds the perfect level of padding for each step. And did we mention how perfect each detail is, such as the front gold trim?
One reviewer said the shoe is “everything you want in a heel” and that the “insoles are crafted so well,” and we couldn’t agree more.
Available in green, nude and black, this strappy heel features knotted straps, a chunky block heel and a 90’s style. You’ll be strutting through the streets with ease.
“I love these heels!!!,” one reviewer said. “The green is so cute for adding a bit of color to a neutral outfit. I have flatter feet and these are comfortable for me with a block heel.”
What does “nude” even mean? Well, it depends on your own individual skin tone, and thankfully Naturalizer understands that.
A part of their “True Colors” collection, the Vera Dress Sandal comes in eight different nude shades so you can find you perfect match.
Better yet, the block heel, ankle strap and Contour+ technology make for superior comfort. One reviewer even shared that the heel was still beyond comfortable after six straight hours of wear.
Further heel features include a leather leather or suede upper, an open toe, an adjustable buckle closure and more.
If you are looking for an ultra-comfortable heel for your wedding day, you found it.
Not only is the Sara in Soft Gold a high-heel that combines a block heel, hidden elastic and a custom-designed insole with arch support, but it also looks incredible. After all, you deserve to go all out for your wedding shenanigans.
Instagram influencer Kari S. even said, “Can we just talk about these gold sandals? They are comfy, people. COMFY.”
Gorgeous and eye catching, these heels will make a statement wherever you go.
The lower heel provides lift while the padded footbed allows for comfortability. And who doesn’t want to be comfortable when dancing the night away?
A content reviewer said she wore these “all night in New York,” a city who loves walking, and they “were so comfy.”
The cult-classic Everlane The Day Heel is back in stock, but there’s no guarantee it’ll stay that way. After all, the brand itself says it’s “a heel you can walk in. All. Damn. Day.”
“So comfortable and didn’t need any ‘breaking in’ time,” one reviewer raved. “[I] went back to work after a year of wearing trainers so needed something comfy, stylish and versatile and this one ticks all the boxes.”
Choose from black, bone stacked or light taupe leather colors. The ballet-inspired silhouette features a rounded toe, a two-inch block heel and an elasticized back.
When it’s just named “The Heel,” you know it’s going to be good.
The Heel comes in five various designs and color, with size and width options available. The shoe also includes details such as a supportive fit that molds with wear, an Italian calf hair upper and leather lining, five mm of plush foam padding and a 2.5-inch heel.
Reviewers rave about the amount of padding The Heel features, claiming they actually “want to wear them.”
With a retro-inspired design, round toe, chunky heel and knit upper, these Vivaia heels are next level. Best of all, customers agree that they are worth the buck.
“They really do feel quite comfortable,” said a shopper, “perhaps more so than the flats I wear!”
With a name like LifeStride, you’re guaranteed a comfortable commute.
These unique heels come in four different statement designs, while they are all made with a simple upper that adds traction and stability — two musts for those on the go.
“They are super comfortable (I wore them for 10 hours on my feet most of the day) and look super sexy,” shared a reviewer. “I even had someone ask to take a picture of my shoes!!!!!”
Simple to wear but gorgeous enough to make a statement, this Madewell mule features leather straps, a wood heel and elastic panels.
“Wow these shoes are amazing!” said a happy customer. “They’re extremely comfortable (and I never wear anything with a heel) so I’m so happy with this purchase. If you’re debating on buying them, I 100% suggest you do. You won’t regret it!”
As the brand says, this is a “timeless pump that can go from desk to date to dance all night.”
One reviewer said, “These pumps are not only beautiful but comfortable. I have never been able to wear a pointed toe shoe before these.”
Made with a super thin insole while still delivering a striking silhouette and ultimate comfort, you can’t pass these F.Major pumps up. Best of all, they are sleek, clean and are available in nappa or patent options.
We have these in our own closets, and trust us, they’re too good to pass up on.
If you’ve been searching for comfy high heels, then it’s your lucky day.
The Canada-designed and Brazilian-made shoes are crafted with an orthotic insole, shock-absorbing platform, non-skid outsole, deep heel cup and rocker sole. Combine all of those features together, and you get a heel that doesn’t only look good but feels good, too.
“Amazing,” said a reviewer describing the shoe. “The fit, the feel, the style. I can’t say enough about these beauties! I can’t wait to buy more.”
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