The heeled flip-flop trend is everywhere — but most pairs are painful. These 4 are actually comfortable

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This summer, the humble flip-flop has gotten an elegant upgrade in the form of a sleek kitten heel. The heeled flip-flop trend is everywhere, but there's one problem: almost every version is uncomfortable. So, I tested lots of cute versions to find the pairs that you can actually walk in.

If you ask me, this sudden excitement about heeled flip-flops has a lot to do with the "hybrid shoe" trends we've already seen — like ballet sneakers and Mary Jane trainers (my favorite version is from Loeffler Randall). In any case, it's clear brands are turning to duality for innovation.

And while hybrid shoes may look cool on the runway, it can be hard for brands to actually make them wearable for consumers. When we first saw the heeled flip-flop trend emerge, I tried one pair and immediately got the sensory ick. The high heel pushed my feet against the toe post, causing friction and pressure on the sensitive skin between my toes. Walking in them felt even worse.

Once summer swept in and the heeled flip-flop trend was bigger than ever, I set out to find the pairs that are cute, trendy, and above all, comfortable.

For more of our summer shoe coverage, see our articles on the best flip-flops with arch support, the most comfortable heels, the best walking sandals, and more.

A quick look at our picks

Best overall: Naturalizer Tressa Dress Sandal

The Naturalizer Tressa Dress Sandal ended up being the winning flip-flop heel in my guide to the most comfortable heels. It has the same clean, barely-there look that makes thong sandals feel so current, but it is built in a way that makes it much easier to actually walk in.

The walkability comes down to how the shoe is made: the cushioned sole, arch support, and curved shape cradle your foot, so it stays put instead of sliding forward with every step.

That made a bigger difference than I expected. I didn't feel like I had to grip the shoe with my toes or brace myself against the thong strap just to keep it on. My foot felt supported from underneath, which took a lot of the pressure off the sensitive area between my toes.

The 2.5-inch heel also hits a sweet spot: high enough to make an outfit feel dressier, but not so high that it starts to feel like a true high heel. And because it is a simple slip-on, it still has the easy, casual feel of a flip-flop.

Worth the splurge: M.Gemi Marta

M.Gemi is one of our favorite places to shop for classic Italian leather shoes with thoughtful construction. But The Marta proves the brand can bring that same level of craftsmanship to a trendier style.

It has a lower heel than most picks on this list, which also makes it one of the most wearable choices. And it gets major points for this clever strap:

It is the most walkable heeled flip-flop I've tried, and the soft leather and sleek shape make it feel a little more elevated than the other pairs on this list. I've been wearing it on repeat with breezy dresses, linen pants, and basically anything I would pack for a summer vacation.

Check out our M.Gemi review to hear about our other favorite styles from the brand.

Most stylish: Dolce Vita Daksie Heels

These kitten-heel flip-flops from the trendy shoe brand Dolce Vita are an influencer favorite. They have already sold out on the site once, and the exact pair above is due for a restock. But there are still plenty of styles available, like a raffia version with shells and a black style with gold beads.

Are these the most comfortable flip-flop heels? No. But are they the cutest, the ones that get me the most compliments, and the ones I daydream of wearing on the Amafi coast? Yes. My favorite outfit I've styled with these is an all-white linen set that made the shoes the centerpiece of the look — and I am definitely going to repeat it the next time I go on vacation.

Just be aware that the Daksie Heels aren't built with the same attention to comfort details as the other picks on this list. The construction is pretty basic, so don't expect a padded footbed or comfort-designed straps.

Best wedge: Steve Madden

These flip-flop wedges are from Steve Madden, and they look very much like the (albeit lower) pair I had as a middle schooler. The brand is famous for its chunky platforms (these black stompers are iconic for a reason), but I tend to avoid hefty shoes because I'm already petite and they look unbalanced on me. But these have the opposite effect: the clear strap and nude heel create the illusion of elongated legs, which I love.

The footbed is squishy, which is my favorite feature in a shoe. And the clear straps are thick enough that they won't cut into you like some other rubber straps I've tried. Plus, the wedge does make these way more stable than kitten heels.

For a shoe this neutral and casual, they certainly add a lot of oomph to your outfit.

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