Most Comfortable Heels for a Stylish Work and Play Look

 

By Hannah McKennett // August 2, 2025

You know the old adage: beauty is pain? Here at GWS, we’re big fans of shoes, which means we also know the struggle of a painful stiletto. That’s why we made it our mission to round up the most comfortable heels for all styles!

Whether you’re looking for the perfect pumps to say “I do” in or some stylish wedges to wear to work, we’ve found the heels that walk the walk. They can withstand everything from a day of walking to a night of dancing, all while looking effortlessly chic at the same time!

So if you’re ready to take your strut to new heights, scroll on for the most comfortable heels for the job — plus some expert tips for finding your perfect comfy pair!

What Kind of Heels Don’t Hurt?

What Comfort Cues to Look for In a Heel

If you’re looking for heels that don’t leave you in a world of hurt (and blisters) after a day of walking, here are a few key comfort cues to consider!

  • Chunky Heel: Thick block heels give you more stability than thin stilettos, which will increase comfort and make walking much easier. When you have a chunky heel that’s as wide as your foot, you’re less likely to feel like you’re balancing on stilts as you walk (which also minimizes the risk of injury). Bring on the dance floor, the long commute, or the hours of standing!
  • Lower Heel: Lower heels, such as kitten heels, also tend to be more comfortable than their sky-high counterparts. They feel more natural on your foot and are less likely to put a strain on your arch and the ball of your foot. Going down even one inch will give your feet major relief, without sacrificing the elegance of an elevated look.
  • Cushioned Insoles: Everything is more comfortable with a cushion, and your heels are no exception! Give your feet the padding they deserve with heels that feature gel or cushioned insoles. This will absorb the shock of your feet hitting the ground and ease some pressure off your toes (and even your lower back).
  • Wide Toe Box: Is there anything worse than squished toes? We think not, and that’s why heels with a wider toe box are lifesavers when it comes to comfort (and bunion avoidance). Look for square-toe styles versus pointed ones, or even opt for heels with an overall wide fit. This will give your feet plenty of room to breathe, which is essential after a long day of walking or standing.
  • Soft and Malleable Materials: Avoid blisters at all costs with heels made from soft and malleable materials, like leather and suede (this also applies to vegan leather and faux suede!). These heels will mold to your feet over time, which is more comfortable than ones made from stiff materials like lucite or perspex. No amount of beauty is worth that pain!
  • Adjustable Straps:For the comfiest fit, look for straps that are adjustable or have a bit of stretch. This will keep your heels fitting perfectly, even as your feet start to swell (which is super common if you’re planning on standing in your heels for hours). Thicker strapsalso offer more support and are less likely to leave you with a swarm of blisters after a long day on your feet.
  • Ankle Support: We’ve all seen the videos of runway models whose ankles give out while walking in their sky-high stilettos. Avoid this IRL with heels that feature ankle support. Look for ankle straps, laces, or designs that will keep your foot in place as you strut your stuff down the runway — or the sidewalk!

How We’ve Created Our List of the Most Comfortable Heels – Why Each Pair Made the Cut

When curating this article, we took every step necessary to ensure that each pair of heels featured is as comfortable as possible.

Many of these heels we’ve test-driven ourselves, and others have been raved about by our GWS readers (aka: you!). For the rest, we spent hours pouring over customer reviews so you don’t have to — and below are the top 27 that made the cut!

GWS Pro Tip: When searching for the most comfortable heels, always read the reviews. Aside from details such as heel height and cushioned insoles, the reviews are the best insight into how comfortable a pair of heels truly is. Plus, you can get crucial information about whether or not you should size up or down.

Triple Layer Insole

Most Comfortable Designer Heels

There’s something about a gorgeous pair of designer heels that makes our hearts skip a beat. But just because a pair of pumps has a designer label doesn’t necessarily mean that they’re comfy!

To help you level up your fashion game without suffering the consequences of a painful stiletto, we’ve rounded up THE most comfortable designer heels for all styles.

From world-renowned fashion labels to gorgeous bridal designers, these are the best heels for an instant confidence boost — as well as a literal boost! And just as comfortable as they are stylish, these heels are about to be your new favorite wardrobe staple.

Most Comfortable High Heels for Wedding Guests: These Nude Platform Sandals

These Adriana Platform Sandals by Elizée are proof that you can dance all night without kicking off your heels. Crafted from ultra-soft Italian leather with a cushioned memory foam insole and a sturdy block heel, they deliver serious comfort without skimping on style. The nude blush tone makes them endlessly versatile for any wedding guest outfit, while the platform design gives you height and stability.

Chic, wearable, and whispering “let’s do one more round on the dance floor.”

What to Wear So Your Heels Don’t Hurt

While all of the heels on this list are designed to be comfortable on their own, there are a few extra add-ons you can wear to make them even cozier.

In addition to the comfy built-in padding, we recommend adding a pair of comfortable cushioned insoles to your heels, especially if you plan on wearing, walking, or standing in them for long periods of time. A good pair of invisible insoles will give you all the arch support and cloud-like padding you need!

If you’re breaking in a new pair of heels, you may also want to wear some precautionary blister cushions. Like a plush bandaid, you can stick these onto the areas where you would potentially get a blister, such as the back of your ankles or the side of your toes. They’ll stop the heels from rubbing on your skin, ensuring that you stay comfy for longer!

Author

Hannah McKennett is the Features Writer at Green Wedding Shoes, known for curating fashion-forward yet functional style stories for modern brides and readers alike.

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