Do Comfortable Heels Really Exist?
Catherine Hageman, the voice behind Small Town, Big Wardrobe, discusses her search for heels she can wear all day long.

The comfortable heel is the working woman's Holy Grail, and I have spent years testing countless pairs, searching for ones that don't kill my feet.
I sometimes carry my heels in my work-bag and wear flats on the way to the office, even though my walk to work lasts about two minutes. I occasionally (okay, most of the time) tote an emergency pair of flats just in case that day's heels are too much.
But, there's a part of me that wishes I was the girl who could wear very high heels all day. My friend, Caitlin, is always in at least three-inch heels. She swears her feet hurt more when she wears flats. I am infinitely jealous of her heel-wearing ability. Or pain tolerance.
Thankfully, I have found a few pairs of comfy heels, and learned that the two features to look for when buying all-day heels are a platform and a chunkier heel. These Talbots sandals may be four inches high, but their wider heels mean you'll last in them. Nine West makes some of my favorite shoes (like this red pair) and include a cushioned foot-bed. (I just ordered these leopard pumps because one cannot have enough leopard shoes). I'm newly obsessed with Target's five-inch platforms that I swear are all-day walkable.
If pumps aren't your style, wedges give height without sacrificing comfort. I own these Target wedges in black and gray (I couldn't decide!) and wear them all day without pain.
I'd love to hear if you've found some comfortable (or even simply bearable!) heels of your own. After all, part of the fun of the comfortable heel hunt is the many pairs you have to buy and try to find the perfect ones.
Catherine Hageman dispatches fashionista tendencies fit for a corporate career on Small Town, Big Wardrobe.
Stay In The Know
Get exclusive access to fashion and beauty trends, hot-off-the-press celebrity news, and more.
-
32 Pretty Bronde Hair Shades, Worn by Celebrities
Can't decide between blonde and brunette? Have both. Can't decide between blonde and brunette? Have both.
-
Trust Me—Your Spring Beauty Routine Deserves an Upgrade From April's Best New Products
Kickstart your seasonal refresh with these editor favorites.
-
Summer Workwear Outfits You Can Recreate This Week
Sort your workweek style ASAP.
-
Granny's Freaky Gardening Clogs Are Summer 2025's New Lo-Fi Shoe Obsession
The style has quietly morphed into this summer’s cult obsession.
-
The Summer 2025 Shoe Trends Stylish Women Will All Wear in Two Months
Get a head start.
-
Flat Shoes Can Be Cool—These 40 Trendy Pairs at Nordstrom Prove It
Comfort rules.
-
Take It From a Fashion Editor: These Summer 2025 Trends Are Certified Compliment-Magnets
Don't wait until June.
-
Trump's Tariff Chaos Forces Women-Led Brands to Strategize and Adapt—Fast
Independent designers have the most to lose, and shoppers will feel the impact.
-
These Best-in-Class Brands Thrive by Staying Small
Forget dominating an entire fashion industry. These labels are satisfied with perfecting a single category.
-
Black Pumps Are Out—Everyone Is All-In on White Heels
Fashion insiders approve.
-
I’m Crafting a Rich-Looking Wardrobe With These Luxury Spring Accessories
Follow my lead by shopping on-sale styles from SSENSE, Neiman Marcus, and Bergdorf Goodman.