While it may seem like fashion editors care more about how shoes look than how feasible they are to walk in all day, take it from us that it’s a myth—we care about
comfort just as much as style. And although we may sometimes wish that we could get away with wearing flats every single day, we frequently find ourselves reaching for heels, and more often than not, it’s our most comfortable heels that we’re reaching for.
While we Who What Wear editors all have different tastes and preferences when it comes to style, we’ve tried out a lot of shoes in our time, so we know what styles and brands are worth taking off your trusty flats for. And while we love a good wedge or platform heel, the options below are our picks of the more daring options—think stilettos, kitten heels, etc. Some events just happen to call for them, so we put together our favorites that are 100% worth investing in. Need some new stylish, walkable shoes of your own for that next night out? Keep scrolling.
“In my opinion, Gia Borghini can do no wrong when it comes to cool shoes. And here’s the great news: The brand’s shoes are also extremely comfortable. I specifically need to call out these cloudlike padded heels designed by Pernille Teisbaek, which I actually want to own in every color.”
“These are my new go-to party shoes, and I’m obsessed. I love the neutral color because it goes with basically every dress I own. Plus, the strappy silhouette makes them fun and festive for the holidays. They have a modest two-inch heel that’s dressy but not hard to walk in, and they have never given me blisters.”
“If you ask any of my fellow editors, you know that I basically live in heels. So I don’t say this lightly: Steve Madden is one of the most underrated comfortable, affordable, and durable brands to shop for heels. I’ve owned my fair share of heels from the brand, but these stunning chain ones have to be the chicest and comfiest I’ve owned yet.”
“Some heeled boots seem like a great idea until you’re trying to escape the frigid air in a rush. For me, no other ankle boots have quite been as comfortable to move around NYC in as Vince Camuto’s Presindal Booties. They actually are far more comfortable than a lot of my chunky-heeled boots, and they’re so easy to style, making them perfect for any occasion.”
“I’ve always found Staud heels to be really comfortable, which is fortunate because I’d buy them even if they weren’t. (They’re that cute.) They all have cushioned insoles, are made of soft leather, and have walkable heels. My go-to pair is currently sold out, but I lost it when I saw these sparkly heels. They’re perfect for the holidays.”
“Manolo Blahnik knows how to make a good high heel. This can be proved by the fact that my style icon, Carrie Bradshaw, never seems to have a blister but also wears them all over Manhattan. Fictional characters aside, another fashionable woman I admire, Anna Wintour, has claimed they’re the only high heel she’ll wear to an event. That’s how comfortable they are, and these two women, plus many more, convinced me to buy my first pair. I can confirm that no matter what height you choose from its collection, you’ll be happy with your results. These slingback pumps are my personal favorite.”
“I’ve walked too many miles to count in these black heels from BY FAR with remarkably little pain or discomfort. I think it’s due, in part, to the thicker strap in the front, which nicely molds to your foot shape. It doesn’t hurt matters that they’re extremely stylish and classic and go with just about every garment in my wardrobe.”
“I happen to be partial to low heels in general, but this pair is more comfortable than any other I own. I attribute it to the not-too-thin straps and their perfect placement. I could wear them all day and with literally any outfit.”
“After trying what seemed like dozens of shoes, I actually ended up wearing a pair of strappy sandals from Zara on my wedding day. They were more comfortable than some of the typical wedding shoe options, and I get major wear out of them anytime I need to dress up. Plus, they always come out to be under $100, which is a rare find for nice heels.”
“I usually opt for boots with a chunky heel, but these printed boots were too good not to get. While the pencil heel made me nervous, I wear them all the time. Our editorial director, Lauren, is also a big fan, so you should take a look at their restock because they sell out fast.”
Next, Kate Moss and J.Lo Wore These Boot Trends in the ’90s—Surprise, They’re Back