The 7 Most Iconic Ankle Boots of All Time

Hannah Almassi

We're approaching ankle boot season, and while there are many shiny new pairs of shoes to hold our gaze, a handful of iconic styles still remain at the top of any self-respecting shopping list. Ankle boots, to me, speak of versatility, practicality and being worn into the ground—a perfect pair will be scuffed to death a decade later, carrying many great outfit memories to the cobblers as you get them fixed for the umpteenth time.

Cassie Smart, MatchesFashion.com's buying manager, shoes and bags, agrees. The store is celebrating the most iconic, still-available ankle boots of all item—working with the brands in question to create special, exclusive versions as well as ensuring that they have the old favourites in tow. It's called its Greatest Hits project, and as far as no-regrets purchases go, it's a safe space indeed.

"Greatest Hits is a great way for the customer to buy into a style that may have sold out the first time due to the storming success from the runway," Cassie says. "Other styles that play on the greatest hits trends and what we have bought into this season are the Maison Margiela Tabi boots, as well as the definitive Isabel Marant Dicker boots, Chloé Susanna and the cult Balenciaga cutout boots.

"We love the Vetements disco star boot that was originally an exclusive to us a couple of seasons ago and saw a sell-out success, so we have bought back into this style for A/W 17. Similarly, when we launched the sock boot with lighter heels, these sold out within two weeks of coming in."

So without further ado, let's take a trip down memory lane and revisit the most iconic ankle boots of all time—that you can still buy now.

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