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Of all of the types of shoes in existence, the flat ankle boot is one of the few styles that I don't own. Looking at these ones from River Island, though, I find myself thinking that's probably something I should rectify, because I can easily imagine wearing these with skinny jeans or a casual dress: they'd be comfortable enough to walk for hours in, and would add a bit of a rockier edge to your outfit. The buckles give them a "piratey" look (if that's not a word then it should be), and they look like the kind of boots that will get better with age - or the kind of boots that Kate Moss/Sienna Miller would wear. They're £54.99 and are also available in tan.

Related: Shelly's front zip ankle boots | Faith pointy ankle boots | Nine West ankle strap shoes