Sorry, Stilettos, But These '90s-Inspired, Prada-Coded Anti-Flats Are Hot on Your Trail

I'm one of Big Stiletto's most loyal fans. If I'm not in a training sneaker, you won't find me in flat footwear, and until recently, a chunkier heel couldn't be sourced from my closet. That is, until recently. In the last few seasons, brands like Tory Burch, Khaite, and The Row sparked an interest in block heels, developing fresh takes on the dated shoe silhouette that made me rethink my strict loyalty to skinny and often unstable lifters. Their heels were thicker and heartier and, as such, quite approachable, even at high heights. At the same time, they were just as sleek as any stiletto I'd ever seen, not to mention fresher and different from my usual rotation. Immediately, I began my search for the perfect pair.

Obviously, there are the classic Tabi pumps, which come in a variety of silhouettes, many with a thicker, cylindrical heel. But if you're not in the market for such a divisive toe shape, don't fret. Most of the below options are far more approachable in appearance, not to mention price, with a mix of high and low prices at your fingertips. Think Massimo Dutti, Zara, and Jeffrey Campbell mixed in with Gucci, Prada, and Celine.

What each of these shoes shares is a '90s look with a twinge of old Prada—the latter is more noticeable in some pairs than others—and an overall cool factor that deserves to be shown off. Wear them with tights and a knee-length wool or leather skirt or dress in the wintertime. In the summer, opt for something lighter, like linen or silk, but in a similar silhouette. You can even style them with fitted trousers for a sophisticated ensemble that still feels youthful and chic. The options are, as they say, endless.

Scroll down to find your perfect pair. I know I'll be busy finding mine.

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