- Share this article on Facebook
- Share this article on Twitter
- Share this article on Email
- Show additional share options
- Share this article on Print
- Share this article on Comment
- Share this article on Whatsapp
- Share this article on Linkedin
- Share this article on Reddit
- Share this article on Pinit
- Share this article on Tumblr
If you purchase an independently reviewed product or service through a link on our website, The Hollywood Reporter may receive an affiliate commission.
Finding comfortable heels can be the ultimate sartorial challenge. Who hasn’t had a love-hate relationship with stilettos? Sure, they instantly elevate any outfit in every way — not to mention giving you legs for days — but they can seriously hurt. Any shoe lover knows what it’s like to hobble home after a long day. But the best comfortable heels allow you to wear them all day without leaving your feet swollen and covered in blisters.
On top of that, many people who are working from home haven’t worn heels as much during the pandemic — but now that offices are reopening and the event circuit is back in full swing, many Hollywood executives are wearing them again. However, as executive wardrobe consultant Stephanie Gisondi-Little recently told The Hollywood Reporter, “My clients aren’t interested [right now] in anything beyond a one- or two-inch heel.”
For high-heeled inspiration, look to stars like Lady Gaga, who recently paired a vintage-inspired polka dot dress with pointed-toe white heels by Giuseppe Zanotti; and Paris Hilton, who wore Valentino Garavani’s signature studded black heels with a baby blue dress to dinner at Nobu in Los Angeles.
What makes for the most comfortable heels? Look for memory foam foot beddings, thicker heels and strategic silhouettes that help evenly distribute your weight to avoid pain points. Whether you’re looking to dress up wide-leg trousers or laid-back denim, we’ve rounded up some of the best comfortable heels — ranging from luxury designer options to wallet-friendlier styles — that prove you can be both comfy and stylish.
1. Everlane The Italian Leather Day Heel
What’s black and white and chic all over? Everlane’s white leather Day heels, of course. A rounded toe, sturdy block heel and luxe Italian leather give this pair a refined and versatile look — and at two inches, the heel is just the right height for comfort. (Angelina Jolie, Meghan Markle and Katie Holmes have worn Everlane.)
2. Clarks Linvale Jerica Pumps
A classic pair of black heels belongs in every closet, and these effortless pumps by Clarks are certainly a perfect fit. Thank the Ortholite insole and 2.2-inch heels for making these among the most comfortable heels that work for every wardrobe. They’re also available in other colors and prints.
3. Ma’am Shoes Marsha Heels
Mandy Moore and Leighton Meester are among the stars who have slipped into Ma’am Shoes’ comfortable footwear. The brand’s stylish Marsha heels are made of soft Italian suede and feature plush foam padding and a supportive insole, and the two-inch round heel and buckles bring a sense of playfulness to your spring looks.
4. Naturalizer Women’s Karina Pumps
Put it in neutral with Naturalizer’s leather Karina heels, which are also available in suede and more than a dozen other colors and prints. This pair has a square toe and cushioning that sculpts to the contours of your feet. The result: all-day comfort in classic two-inch pumps.
4. Vionic Fleur Heeled Sandals
Vionic has been seen on the fashionable feet of Oprah Winfrey (who has included the brand several times on her Favorite Things list), Alexa Chung and Kristin Cavallari, among others. The comfort-minded footwear label’s Fleur mules stand at 2.5 inches and are designed to support your body’s natural alignment from the feet up. Their Vio-Motion footbed technology provides all the arch support you need, which explains why many of their shoes have the American Podiatric Medical Association Seal of Acceptance. The soft knitted uppers hug your feet, and you can choose from other colors.
5. Tamara Mellon Astral Pillow Top Heels
Part of the Hollywood-loved footwear designer Tamara Mellon’s comfy Pillow Top collection, the Italian suede Astral heels boast a comfy insole made of eight-millimeter high-density memory foam and red carpet-ready design embellished with crystals — so whether you’re headed to a swanky soirée or the office, you’ll feel like you’re walking on clouds. Tracee Ellis Ross, Yara Shahidi and Cindy Crawford are just a handful of stars who have worn the label.
6. LifeStride Cabaret Dress Sandals
If you don’t want to get tied up in strappy sky-high heels that require a tightrope walker’s balance, LifeStride’s Cabaret dress sandals offer a more comfortable alternative. This open-toed design has a stretchy slingback strap, criss-cross details and the brand’s special Soft System cushioning to keep your feet ouch-free. The chunky three-inch heel and traction sole add extra stability.
7. Bernardo 1946 Beaufort Sandals
Weave Bernardo 1946’s leather Beaufort sandals into your spring wardrobe and you won’t need to worry about achy feet. The two-inch block wood heel gives them just the right amount of height and support, plus the cushioned sole keeps footsies happy. This chic silhouette seamlessly transitions from day to night, and pairs well with wide-leg trousers and spring dresses alike.
8. Franco Sarto Racer Pump
Peachy-pink is a pretty alternative to regular beige — it still works as a neutral with a bit more oomph. Super sophisticated, this slingback pump in croc print leather (available in other colors) has a 2.75-inch covered flared block heel that gives it an architectural edge. The rubber sole will help keep you in comfort.
9. Margaux The Uptown Sandals
These strappy leather heels by New York-based, Spain-made label Margaux have five-millimeter plush foam padding and strategically placed straps that won’t irritate or pinch your skin. They’re finished with a 3.5-inch heel and criss-cross design that adds glamour and drama to jeans and maxi dresses alike.
10. Vice Versa Scrunchie Mules
Stylish dressers are essentially getting two shoes in one with Vice Versa’s Scrunchie Mules, which feature a statement-making pointed open toe design and the luxury label’s signature foldable heel that transforms the 3.7-inch silhouette into flats.
11. Aerosoles Evvie Block Heel Sandals
With a 1.75-inch heel height, these comfortable black sandals are easy to pair with maxi dresses and relaxed denim. The polished buckle and block heel make a bold statement, and the shoes are available in other chic shades.
12. Marion Parke Izzy Chunky Block Heel Sandals
Channel Old Hollywood glamour with these gold block heel sandals by Marion Parke, a podiatric surgeon-turned-footwear designer. Made in Italy, these metallic Nappa leather slides have a two-inch heel and feature medical-grade cushioning that molds to your foot over time. They also come in black and sand.
13. Naturalizer Banks Pumps
You can slither around in these snakeskin slingbacks for hours, thanks to Naturalizer’s N5 cushioning that molds to the contours of your feet. These pumps have a slightly elongated toe, a walkable low heel, flexible sole and breathable lining, and they come in spring-ready colorways for brightening your back-to-work wardrobe.
14. Cole Haan Gabbie Pump
For one of the best comfortable black heels that give you more lift without the pain, look to the arch support on Cole Haan’s Gabbie pumps. This black patent leather pair has an elegant almond toe and a 3.5-inch stiletto heel.
15. Chloé Lauren Scalloped Leather Pumps
It doesn’t get any chicer than Chloé’s playful scalloped leather pumps, a classic silhouette that also comes in an equally comfy flats version that’s been spotted on Angelina Jolie, Katie Holmes and Mandy Moore, to name just a few. Made in Italy, these slip-on heels feature a 2.25-inch wrapped block heel, a round toe and leather lining, all of which combine to offer plenty of comfort while walking.
16. Valentino Garavani Rockstud Alcove 60 Leather-Trimmed Mesh Pumps
If you love the edgy look of luxury designer Valentino Garavani’s studded Alcove stilettos (but prefer something less sky-high), then opt for the brand’s equally stylish leather and mesh slip-on pumps with a 2.5-inch heel. These elegant pointed-toe heels are finished with the label’s signature pyramid studs that give it a refined-yet-rebellious aesthetic.
17. Dr. Scholl’s Scout High Wedge Sandals
Is there a brand more synonymous with comfortable shoes than Dr. Scholl’s? Thanks to the covered wedge heel, these sandals give nearly three inches of lift, yet feel like you’re walking on a cloud. The ideal shoe for your favorite sundresses or cutoff shorts, they’ll be on your feet all through the warmer months.
Sign up for THR news straight to your inbox every day