We independently evaluate all of our recommendations. If you click on links we provide, we may receive compensation. Shopping Style Shoes The 14 Best Comfortable Heels of 2024, Tested and Reviewed Platforms, pumps, sandals, and more. By Jamie Fischer Jamie Fischer Jamie Fischer is a commerce writer for Real Simple. She has experience writing content for various digital publications including Parents, and is passionate about home, lifestyle, and beauty products. Real Simple's Editorial Guidelines Updated on August 15, 2024 In This Article View All In This Article Our Top Picks Reviews Final Verdict Our Testing Process More to Consider How to Shop FAQs Take Our Word For It Photo: Real Simple / Beth Martinson Whether you’re commuting to the office or heading to a late-night soiree, a good pair of heels can elevate any outfit. And while you’ve likely heard the expression “beauty is pain,” we’re here to prove it doesn’t have to be. The best heels look good and feel better, leaving you confident and comfortable. We tested 28 pairs of heels at home, evaluating them based on fit, comfort, support, quality, and value. For expert tips on how to shop for the best comfortable heels, we consulted Dr. Lori Weisenfeld, DPM, New York City sports podiatrist, and personal stylist Yael Steren. Read on for our favorite picks, including stilettos, pumps, wedges, and more. Our Top Picks Best Overall: SALE DREAM PAIRS Pump Sandals at Amazon $39 $32 Jump to Review Best Everyday: Everlane Italian Leather Day Heel at Everlane.com $178 Jump to Review Best for Office: Vivaia Round-Toe Chunky Heels at Amazon $150 Jump to Review Best Statement: Charlotte Stone Belle at Charlotte-stone.com Jump to Review Best Pump: SALE Clarks Ambyr Joy Pump at Amazon $95 $46 Jump to Review Best Stiletto: Inez Diana Heel at Inez.com Jump to Review Best Platform: Soda Account Open Toe Lug Sole Heel at Amazon $27 Jump to Review Best Mule: SALE Aerosoles Entree Shoe at Amazon $99 $60 Jump to Review Best Loafer: Rothy's The Lug Loafer at Rothys.com Jump to Review Best Sandal: Dolce Vita Braided Sandal at Amazon Jump to Review Best Overall DREAM PAIRS Pump Sandals PHOTO: Amazon $32 at Amazon View on Dreampairshoes.com What Stands Out These versatile heels are shockingly comfortable, requiring no break-in period. What Could Be Improved The toe strap may hurt your feet if worn for longer periods. Timeless and comfortable, the Dream Pairs Pump Sandals earned our title of best comfortable heels. When we first began testing them, they were comfortable right off the bat. They fit true to size and required no painful break-in period. We found the 3-inch heel to be the ideal height, and the arch support felt perfect. The straps were similarly comfortable, though they did get a bit uncomfortable on our toes when we wore them for longer periods of time. Available in 30 colors—including simple nude hues and more adventurous glitter options—these heels will work with pretty much any outfit. Despite being on the dressier side, we were able to wear them with basic jeans and formal dresses alike. After six months of use, the heels are still exceeding our expectations: They have maintained their high quality with no visible signs of wear. Given their impressive durability and classic design, we think these heels are here to stay. Heel Height: 3 inches | Size Range: 5–12 | Material: 100% suede | Outsole: Rubber Real Simple / Beth Martinson Best Everyday Everlane Italian Leather Day Heel PHOTO: Everlane $178 at Everlane.com What Stands Out The leather is high quality, and the sturdy, low heel makes them suitable for daily wear. What Could Be Improved They don’t offer much arch support. While some heels are for special occasions, others, like the Everlane Day Heel, are comfortable and casual enough for everyday use. When we first slipped them on, we knew right away that these would be some of the most comfortable ones we tested. Since they’re low to the ground—only measuring 2 inches in height—they felt sturdy on our ankles. We also appreciate the elastic on the back, which gave our feet some room to move and breathe. Crafted from Italian leather, these heels scream high quality. They come in six rich colors, along with the option of a “narrow” or “comfort” fit. It’s worth noting that these heels don’t offer much arch support, and our foot did get a bit tired after hours of wearing them. Despite this, we found them to be well made, and they didn’t feel flimsy at all. Even after six months of use, the leather has held up perfectly. Thanks to their durability and manageable height, these make a great beginner pair for those just starting to wear heels. Heel Height: 2 inches | Size Range: 5–11 | Materials: Leather | Outsole: Leather Real Simple / Jessica Vadillo Best for Office Vivaia Round-Toe Chunky Heels PHOTO: Vivaia $150 at Amazon View on Vivaia.com What Stands Out The low, chunky heel is secure enough to run around in. What Could Be Improved They may cause blisters during the first few wears, but this will improve over time. When searching for the perfect office shoe, you need something formal, comfortable, and durable enough to survive a long commute. Luckily, the Vivaia Julie Pro Round-Toe Chunky Heels check all the boxes. After several wears to the office and around the city, these heels were surprisingly comfortable. The footbeds have a silky-smooth quilted cushioning that was soft on our feet and provided ample arch support. Plus, the round toe provided the perfect amount of wiggle room—it was loose enough to let our feet breathe but not too big to the point that they were coming out of the shoe when we walked. These heels come in two versions: a basic version, and an option with upgraded pressure relief insoles. The material has a lot of give, making this an excellent choice for those with wider feet. We found the material to be high quality, and the chunky block heel felt thick enough to keep our ankles secure on uneven surfaces. After wearing them for six months—in many inclement weather conditions, at that—they still look as good as new. The first time we wore these heels, the fabric rubbed against the back of our feet, creating blisters. However, once we started wearing them regularly, we no longer experienced any redness or pain. In fact, we were eventually able to wear the shoes for seven-hour intervals with no discomfort whatsoever. Even while running (yes, literally running) to catch a train, the heels felt supportive and secure. Heel Height: 1.77 inches | Size Range: 5–11 | Materials: Knit with a blend of polyester, cotton, and recycled plastics | Outsole: Rubber Real Simple / Anna Popp Real Simple / Anna Popp Best Statement Charlotte Stone Belle PHOTO: Charlotte Stone View on Charlotte-stone.com What Stands Out The vibrant shoes offer the comfort of flats with a stylish heel. What Could Be Improved They are a bit pricey and not practical enough to complement many outfits. Whether you often experiment with bold prints or tend to stick to neutrals, the Charlotte Stone Bell Strappy Sandals will add a pop of color to any look. While these shoes don’t match with much, we think that’s part of the allure—they’re rainbow statement sandals, after all. In addition to their vibrant design, these shoes proved to be shockingly comfortable—we would even go as far as to say that these are some of the most comfortable heeled sandals we’ve ever worn. With a low block heel, they offer the comfort of flats with the elevated look of classic heels. The soft suede straps have a high-quality feel to them, and the memory foam insole provides the perfect amount of cushion. Just be careful not to twist or snag the thin straps as you take the shoes on and off. We expected the vibrant colors to fade or get dirty over time, yet they somehow maintained their pristine condition, even enduring long vacations and trips to the city. After six months of use, they have held up beautifully. Just keep in mind that these heels are more of a summer shoe and they’re on the pricier side, so they may be a hefty investment for one season. But if you want a chic way to incorporate color into your all-black wardrobe, these are a no brainer. Heel Height: 2.5 inches | Size Range: 4–13 | Materials: Leather or suede | Outsole: Leather Real Simple / Taylor Fox Best Pump Clarks Ambyr Joy Pump PHOTO: Amazon $46 at Amazon $64 at Zappos $95 at Kohls.com What Stands Out The heel is a bit thicker than that of a typical stiletto, making it easier to walk in. What Could Be Improved The toe box runs a bit small, and the top of the shoe may dig into your skin if you don’t size up. These classic black leather pumps are the closet staple you’ve been searching for. The sleek design and timeless aesthetic make the shoes incredibly versatile—they’re sophisticated enough to wear to the office and fun enough to wear for a night out. As far as heels go, we found these to be pretty comfortable on the first wear. The cushioned soles were especially cozy, though it did take us some time to get used to the air squishing as we walked. We were also impressed by the well-made construction; the leather material felt thick and durable, and the arch proved to be similarly supportive. With a 3.35-inch heel, this isn’t a beginner pair, and it may be a bit high for everyday wear. But despite the height, the heel has a wider circumference than a typical stiletto, making it a bit sturdier and easier to walk in. Note: We found the heels a bit snug, and the top part dug into our foot a bit, so we recommend sizing up from your usual size. Heel Height: 3.35 inches | Size Range: 5–12 | Material: Leather | Outsole: Thermoplastic rubber Real Simple / Mandy Wood Real Simple / Mandy Wood Real Simple / Mandy Wood Best Stiletto Inez Diana Heel PHOTO: Inez View on Inez.com What Stands Out The black suede sandals are versatile enough for summer and winter wear. What Could Be Improved The toe box makes your toes look squished. If you’re new to wearing heels, high stilettos may feel daunting, but the Inez Diana Heels stood out for their comfort. They’re available in sizes ranging from 6 to 10.5 and offer three width options: slim, standard, and roomy. Despite their lightweight, sandal-like feel, these suede heels are equally suitable for the winter months. The surprisingly breathable material kept our feet from sweating, even on hot summer nights. After six months, the fabric still looks flawless. We found these shoes to be comfortable right out of the box, requiring a minimal break-in period. They feature ankle straps for extra security, which fit us just right with no rubbing, tightness, or looseness. The toe box felt similarly comfortable, though we did take some issue with its appearance—while we didn’t experience any discomfort, the shoes made our toes look more squished than they felt, and we weren’t fans of the visible toe cleavage. We wouldn’t necessarily commute to work in these heels, but they were perfect for social events. We were able to walk around and mingle all night long, without any blisters. These shoes are on the snugger side, and we found them a bit uncomfortable with tights. The 3.5-inch heel is also fairly high and thin, so this isn’t the best choice for those seeking a more sturdy, stable shoe. However, it comes in a 2.8-inch version, which offers a nice middle ground. Heel Height: 3.5 or 2.8 inches | Size Range: 6–10.5 | Material: Suede | Outsole: Leather with rubber insert for grip Real Simple / Morgan Ashley Parker Real Simple / Morgan Ashley Parker Best Platform Soda Account Open Toe Lug Sole Heel PHOTO: Amazon $25 at Amazon What Stands Out The durable platform sneakers have a secure ankle strap and impressive traction. What Could Be Improved They don’t offer much arch support. Besides sneakers, we consider these platform sandals to be some of the most comfortable shoes we’ve ever owned. In fact, we were able to wear them consistently for over eight hours a day with zero pain. They fit us true to size and feature an adjustable strap, allowing you to tailor them to your foot. We found the strap to be smooth to the touch and completely comfortable, even on muggy days. Thanks to the thick straps and impressive traction, we tackled every type of terrain with ease: wet and dry pavement, smooth indoor flooring, carpet, grass, sand, dirt, uphill, downhill, and everything between. It’s worth noting that these soles don’t have much cushioning or arch support, so they may not be suitable for those who require more. That said, we didn’t experience any arch pain while wearing them. We were especially impressed by their durability—after running around in the summer heat, the upper fabric hasn’t cracked, and the soles look as good as new. Even after six months of nonstop use, they’ve suffered no more than a few scuffs on the bottom. Plus, the material is easy to clean with a moist paper towel. Heel Height: 2.75 inches | Size Range: 5–11 | Materials: Imitation suede, nylon camouflage, synthetic leather | Outsole: Synthetic rubber Real Simple / Elise Wojczyk Wang Best Mule Aerosoles Entree Shoe PHOTO: Amazon $60 at Amazon View on Dsw.com $99 at Macy's What Stands Out The thick, chunky heel is easy to walk in. What Could Be Improved You may experience chafing over time. Available in seven colors, these mules are sure to match any look. Due to their thick and chunky style, we found these heels very stable and easy to walk in. We especially appreciate the manageable height—just 2.25 inches—which provides a bit of lift without being too tall. The padding on the soles offers great arch and ball support, and we were impressed by the traction. Plus, the open-toe and -back design make these a particularly breathable choice (perfect for summer heat). Despite arriving with a small scuff on the toe strap, we found these shoes to be of very high quality. Initially, we experienced no rubbing or chafing, nor did we suffer from any blisters or foot pain. However, after six months of use, the chafing became pretty extreme. That said, we warn against wearing these shoes too often. Still, we think they’re a comfortable, high-quality choice. Heel Height: 2.25 inches | Size Range: 5–12 | Materials: Faux leather | Outsole: Thermoplastic rubber Real Simple / Sophie Mendel Real Simple / Sophie Mendel Best Loafer Rothy's The Lug Loafer PHOTO: Rothy's View on Rothys.com What Stands Out Crafted with rugged soles and washable fabric, these heels are very sturdy and durable. What Could Be Improved They aren’t very breathable and require a short break-in period. Mature and stylish, Rothy’s The Lug Loafers make a great addition to any wardrobe. Available in black or brown, these basic shoes can complement any outfit. Plus, the 1.5-inch heel makes them casual enough for everyday wear. We found them timeless enough to wear to brunch, dinner, work, and just errands. These loafers took a bit of time to break in, and we needed a small bandage at first, but after a few wears, they were fine. Our arches felt incredibly supported in these shoes, and the padded insoles and rugged outsoles offered the best traction we’ve seen in a loafer. They even include lugs on the heel and outer sole (which you’d never see unless you looked at the bottoms). Given their sturdy construction, we expect these shoes to hold up well in rain or shine. After six months of use, we’ve noticed no changes in quality. Thanks to their rugged soles and washable fabric, we expect these shoes to last for years. It’s worth noting that these aren’t the most breathable heels. However, the cozy warmth makes them suitable for fall or winter. We recommend sizing up for added breathability and comfort. Heel Height: 1.5 inches | Size Range: 5–13 | Materials: Knit with a blend of RWS-certified Merino wool and recycled plastic bottles | Outsole: Lug (rubber) Real Simple / Ivy Ford Real Simple / Ivy Ford Best Sandal Dolce Vita Braided Sandal PHOTO: Nordstrom View on Amazon $60 at Zappos $25 at Macy's What Stands Out The straps keep your foot secure without applying too much pressure. What Could Be Improved They chafe a bit on the right pinky toe. A chic yet well-fitting sandal is hard to come by, and this pair from Dolce Vita proves you won’t have to sacrifice comfort for style. While we were initially hesitant about the quality of the braided straps, they certainly proved us wrong—they kept our foot in place without applying too much pressure, achieving the perfect fit. Along with their comfort, the straps also proved to be surprisingly breathable. Truth be told, these shoes didn’t offer much ankle support or traction. However, we think they fared well enough to wear to the office or an event. The slightly cushioned sole was immediately comfortable, requiring minimal break-in time. We like the height and thickness of the heel, but the snakeskin finish wasn’t our style. The only hot spot we noticed was by our right pinky toe, which chafed against the material after extended periods of wear. Since this is a summer sandal, we haven’t gotten much use out of them throughout the winter. However, they’ve maintained their quality throughout six months of infrequent use, and we expect they will hold up well over time. Heel Height: 3.25 inches | Size Range: 5–13 | Materials: Synthetic | Outsole: Rubber Real Simple / Rachel Thalhuber Real Simple / Rachel Thalhuber Best Wedge Vionic Bonita Wedge Sandal PHOTO: Nordstrom $91 at Amazon What Stands Out These wedges boast good arch support and stability on various surfaces. What Could Be Improved The toe area is a bit snug. Compared to other strappy sandals, we found the Vionic Bonita Wedge Sandals’ straps to be smooth and soft. They offered ample airflow, keeping our feet from sweating as we wore them. Our toes occasionally felt smushed, though this is to be expected of most toe straps. After wearing these wedges for six hours straight, we were amazed by the stability and arch support. We wore these sandals on a variety of surfaces—grass, wood floors, carpet, cement, stone, gravel, and polished cement—and didn't slip or trip or roll an ankle once. These sandals are only available in a few sizes, ranging from 9 to 11 depending on the retailer. They also offer limited color versatility, coming in only black, macaroon, and gold. Despite the lack of variety, the neutral colors work with pretty much any outfit. While we haven’t worn them much in the winter, they have maintained their quality. Heel Height: 4.25 inches | Size Range: 9–11 | Materials: Leather and textile | Outsole: Rubber Real Simple / Carolyn Malcoun Best Espadrille Castañer Carina Wedge Espadrilles PHOTO: Net-a-Porter $140 at Amazon $135 at Zappos View on Net-a-Porter What Stands Out The lace-up tie allows you to achieve the perfect fit. What Could Be Improved With a structured canvas toe, these shoes are less ideal for those with wider feet. With a light cork wedge and lace-up tie, these espadrilles make the perfect summer shoe. We found them comfortable enough for running, walking, and standing—we hardly felt like we were wearing heels. They fit like a glove on our first wear, requiring no breaking in or stretching out. Plus, the sturdy canvas and adjustable straps ensure stability and breathability. We would describe the experience of wearing these shoes as walking on a rubber band—solid yet bouncy. The bottom of the shoe has a rubber lining to enhance traction, allowing us to walk without slipping. Frankly, we wish our flatter sandals had the same effect. We never experienced any rubbing or chafing, and we could adjust the tightness based on how we wrapped and tied the ribbon. While the lace-up tie enables adjustability, the canvas toe is fairly structured, so those with wider feet may prefer a more flexible shoe. After six months of use, the quality is still top notch. The shoes are just are just as comfortable as they were on day one, and the material shows no signs of wear. We’ve found that the lace-up straps tend to get a bit wrinkly, but they flatten quickly and have leather aglets to prevent fraying. Over time, these shoes did pinch a tiny bit at the base of the toes but never enough to be super uncomfortable. Overall, they offer the comfort and support of a good pair of flats. Heel Height: 3.25 inches | Size Range: 5–10 | Material: Fabric with leather lining | Outsole: Rubber Real Simple / Elena Garcia Best Pointed Nine West Kuna Pointy Toe Pumps PHOTO: Zappos $99 at Nordstrom View on Ninewest.com $64 at Macy's What Stands Out Despite the pointed toe, the toe box is spacious and comfortable. What Could Be Improved The thin heel isn't very sturdy. While pointed heels aren't exactly known for their comfort, this pair from Nine West blew us out of the water. They fit us perfectly, providing the ideal amount of extra space in the toe box. Plus, they adapted well to our foot’s shape, growing more comfortable with each wear, and provided decent arch and ankle support. We could tell these shoes were high quality just by looking at them. The upper is crafted from a sleek, timeless suede leather, while the memory foam inner sole provides ample cushioning. Our ankles and arches felt fully supported as we walked, too—a testament to their well-made construction. We were also impressed that they required no break-in period. We wore them for 24 hours right out of the box, and they widened and became more comfortable throughout. In fact, we were able to endure a full day in the office without needing to take them off. Even after six months of use, they still look and feel great. Our only complaint involves the heel itself. While it isn't overly high, it's very thin, which felt a bit wobbly and unstable at times. Due to the narrow design, we also suggest avoiding grates in the sidewalk because the heel could get caught. Despite these minor grievances, these heels are great for those who want a classy look with the comfort of a kitten heel. While the spiky heel may not be sturdy enough for beginners, we think those with heel-wearing experience should be good to go. Heel Height: 2.25 inches | Size Range: 4–13 | Material: Leather with synthetic lining | Outsole: Synthetic material Highest Quality Sarah Flint Perfect Pump 85 PHOTO: Sarah Flint $650 at Sarahflint.com What Stands Out The luxurious shoes come in 18 styles and colors. What Could Be Improved The toe box is a bit snug. Handcrafted in Italy, the Sarah Flint Perfect Pump 85s are among the highest quality heels we've ever worn. The leather has a luxurious look and feel, exuding a classy, sophisticated appearance. Plus, they're versatile. Available in 18 styles—including satin, suede, silk, leather, patent leather, and lace—you're sure to find something you like. These heels run true to size, feeling comfortably snug without any rubbing or chafing. We do wish the toe box was a bit wider, though, as our toes felt cramped the first few times we wore them. That said, this is to be expected of pointed heels, and the pinching dissipated quickly. We were also impressed by the padded insoles, as we were able to both see and feel the cushion. And despite the thick padding, the shoes were surprisingly breathable—throughout hours of wear, our feet never felt sweaty or overheated. We'll admit that these shoes are definitely on the pricier side. However, given their well-made construction, we expect they'll last a while—after six months of use, they're still in great condition. If you're in search of a comfortable, durable heel, we think this option is a worthy investment. Heel Height: 3.3 inches | Size Range: 4–13 | Material: 12 options, including suede, leather, calf, silk, and more; leather lining | Outsole: Leather with full rubber forepart Final Verdict Our top pick is the Dream Pairs Pump Sandals for their immediate comfort, impressive durability, and timeless design (they’re available in 30 colors). If you’re seeking a more casual heel for everyday use, you can’t go wrong with the Everlane Day Heel. Crafted from 100% genuine leather, this is one of the highest-quality pairs on our list. Plus, the thick, 2-inch heel makes it sturdy and comfortable enough for daily wear. Our Testing Process To find the best comfortable heels, we tested various pairs at home, focusing on fit, comfort, support, quality, and value. First, we assessed the materials' quality and construction, noting whether the heels, soles, toes, and fabric appeared to be well made. After the initial inspection, we wore each pair at home for an hour, performing everyday activities to break them in. During this period, we noted the initial comfort of the heels and whether we experienced any rubbing, chafing, or pinching. Considering the height and thickness of the heel, we assessed how easily we were able to walk in them and if they offered ample arch support. Next, we wore the heels at least two more times, for two-hour intervals, over the course of two weeks, engaging in various activities including traveling, shopping, running errands, and walking Throughout this period, we observed their breathability, comfort, fit, and support. We also took into account any foot pain or discomfort we endured while wearing the shoes, noting the amount of time needed for them to feel completely broken in. To assess their durability, we examined the heels for signs of wear and tear at the end of the two-week testing period. We continued wearing the top-performing heels for six months, noting how well they held up long term. Real Simple / Sophie Mendel More Comfortable Heels to Consider Calvin Klein Larin Pump: With a sleek, timeless design, these leather heels proved to be particularly supportive, thanks to their cushioned insole and non-slip outsole. However, we did experience some chafing in the toe area, and the leather ripped, making us question their long-term durability. Margaux The Heel: Crafted from Italian Nappa leather, we found these true-to-size heels to be a comfortable, stylish option for both work and dinner settings. The snug fit, memory foam insole, and sturdy 2.5-inch heel were comfortable enough for extended wear, and the rounded toe provided ample breathing room. Our only complaint involves the heel chafing, so we recommend breaking them in before long durations of wear. Real Simple / Taylor Fox How To Shop for Comfortable Heels Like a Pro Heel Height and Shape Whether you’ve gone shoe shopping in person or perused online retailers, you know that heels come in a variety of shapes and sizes. When selecting the right heel for your needs, it’s important to first consider your comfort zone. If you’re newer to wearing heels, you may want to start with a lower, more modest heel, typically ranging between 1.5 and 3 inches. “A lower heel height is going to be much more comfortable than a higher one because there is less weight placed on the ball of your foot,” Steren says. Our favorite pair of loafers, the Rothy’s The Lug Loafers, have a thick, 1.5-inch heel, making them a prime shoe for beginners. As you grow more accustomed to the feeling of walking in heels, you may opt to experiment with taller options, which are typically over 3 inches in height. These heels often have a fancier appearance, though they do take some getting used to. Some heels, like the Inez Diana Heel, come in two height variations, so you won’t have to sacrifice the style you want for your preferred height. In addition to height, the shape of a heel also contributes to its comfort. Block heels, wedges, and platform sandals are typically easier to walk in than thinner heels, due to their broad, stable base. “A good trick to cheat while you're wearing heels is to use a shoe that has a platform on it—if your heel is 4 inches and the platform is an inch and a half, now your heel is really only 2.5 inches,” she says. Plus, platform sandals also tend to have a wider base. Shoes with a thinner, higher heel—like stilettos—are very chic but may require a bit more balance. If you're planning to be on your feet all day, Steren says kitten heels are the way to go. Kitten heels are short training heels—typically less than 2 inches in height—with a slight curvature to them. “Many women have the misconception that kitten heels are matronly, however, that is not the case,” Steren says. “The key is to look for a kitten heel that has a sleek heel, which is not too thick.” Materials The material of your heels plays a significant role in their comfort, breathability, durability, and, of course, aesthetics. Most of the picks on our list have either a leather or synthetic exterior. Vegan or faux leather offer a less expensive, cruelty-free option, but are typically less breathable than genuine leather. If you want a reasonably priced heel to wear once or twice, faux leather is adequate. However, our experts tout the benefits of real leather, so if you’re seeking a long-lasting pair, it may be worth the investment. Other heels, like the Dream Pairs Pump Sandal, are made of suede, a variant of leather with a napped finish. Suede has a unique texture and flexibility, though it may be a bit harder to wipe clean than other materials. Dr. Weisenfeld suggests going with more natural materials. “The natural materials are always going to be more breathable and will expand better with your foot—like real leather vs. vegan leather.” Steren agrees, adding that “a pair of heels made from a supple leather is clearly going to be more comfortable than a pair of patent leather because the former has more give and will mold to the foot.” When it comes to the sole of the shoe, traction is crucial. Traction is what prevents you from slipping, allowing you to walk on different types of terrain. While leather soles are often chosen for their sleek appearance, rubber soles offer the most traction. The Soda Account Lug Sole Sandals, which have a synthetic rubber sole, offered the best traction of all the shoes we tested—we were able to navigate wet and dry pavement, smooth indoor flooring, carpet, grass, sand, and other surfaces with ease. Sizing Finding the right size is a crucial part of shoe shopping—tightness could lead to discomfort and pinching, while looseness may make your foot feel less secure. Sizes do vary by retailer, so you should always check the brand’s specific size chart before you buy. If the website has a customer review section, that may also provide insight as to whether the shoes run big or small. While these methods can reduce the risk of ordering the wrong size, we still recommend checking the return policy in advance. In addition to standard sizing, some shoes are also available in different widths. For example, the Inez Diana Heels come in slim, standard, and roomy. According to Steren, there isn’t one golden rule to follow: “I would say the best is to buy your true size—not to size up or down.” Toe Box The toe box is the area of the shoe that surrounds the toes and is typically either round, pointed, or almond shaped. While toe box shape may not be top of mind while shoe shopping, it can greatly impact the comfort of a pair of heels. Round or almond-shaped toe boxes tend to be the most comfortable, as they're a bit wider and roomier. Due to the extra space, they are less likely to squish your toes. Pointed-toe heels, on the other hand, have a toe box that starts wide and comes to a sharp point. While pointed heels are often considered the most stylish, they aren't normally as comfortable, especially for those with bunions or hammertoes. If you have a wider foot or hammertoes, Dr. Weisenfeld recommends selecting a shoe with a deeper toe box, noting that it will provide a bit more wiggle room. That said, we were impressed by how comfortable the Nine West Kuna 9x9 Pointy Toe Pumps were—despite their severe point, our toes never felt crammed or squished. Questions You Might Ask What type of heels are best for your feet? When it comes to the type of heel, Dr. Weisenfeld says wider heels are better than spike or narrow heels as they more evenly distribute the weight onto your heel. She is a big fan of platform sandals, which provide the elevation of heels with a wider surface for weight distribution. In terms of width, Dr. Weisenfeld says that the vamp of the shoe, or the area where your bunion joint would be, needs to be the widest. For those with wider feet, she suggests trying a more open shoe with adjustable straps. Arch support is also something to consider, as it can reduce pain and enhance comfort. Vionic heels, like the Vionic Bonita Wedge Sandals, are a personal favorite of Dr. Weisenfeld, who commends their arch support and thick soles. How long do heels take to break in? While heels often become more comfortable over time, this is actually a trick question. You should never have to break in a shoe, according to Dr. Weisenfeld: “How many times do we get home and say ‘You know what, this was comfortable in the store but it's not comfortable anymore?’” As the day goes on—especially in hot, humid weather—our feet tend to expand in size. For a shopping hack, Dr. Weisenfeld suggests going shoe shopping at the end of the day, when your feet have already expanded or swelled. She notes that this is also useful because most events at which you would be wearing heels tend to be at night anyway. How can you make heels more comfortable? Regardless of what heels you choose, you shouldn’t expect them to be as comfortable as your favorite flat pair. "It’s illogical to think that you’re going to put your foot into a shoe that's not the same size or shape as your foot, with all the pressure concentrated on the little tiny bones in the front of your foot, and be able to walk around all day or dance all night and be comfortable,” Dr. Weisenfeld says. That said, there are measures you can take to improve the comfort. While insoles and orthotics are often helpful, they may not fit discreetly within a high-heeled shoe. That said, Steren recommends adding a cushion insert to the back of the shoe where the heel hits. Her favorite brand is Foot Petals, which comes in various colors to match all shoe styles. “You can also add in a cushion for the ball of your foot, but keep in mind that it will often make the shoe fit tighter, so it might be a good idea to size up half a size if you choose to use one,” she adds. Dr. Weisenfeld also warns about strappy sandals, noting that thin straps may dig into your skin. To combat this, she says to consider a very sheer pair of stockings, pantyhose, or even cute ankle socks to act as a barrier between the strap and the skin. Take Our Word For It This article was written by Jamie Fischer, a commerce writer for Real Simple. To compile this list, we tested 28 pairs of heels for over six months at home, evaluating them based on fit, comfort, support, quality, and value. For expert insight, we consulted two shoe experts: Dr. Lori Weisenfeld, DPM, New York City sports podiatrist, and personal stylist Yael Steren, who has gained a social media following for sharing her beauty and shopping tips.