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Clarks Indigo Heath Harrier in taupe

I’m really into ankle boots at the moment, especially after my recent purchase of a pair of Clarks Indigo Heath Harrier boots. I’ve been looking for a comfortable, easy pair of boots that I can dress up or down, and I think I’ve found them. I got mine in taupe, though the color is more like a chocolate brown than the grayish brown color I saw online. No matter; they’re still neutral enough to match with lots of things, and the distressed material makes it so I’m not so afraid of scuffing them (which I totally did the minute I put them on, of course).

Even though I love these, I’m having a bit of a hard time styling them. Obviously I’ve worn them with skinny jeans, but can I wear them with other pants that require a larger cuff when folding them up? And then do I wear them with or without visible socks? I’m talking winter looks, not spring/summer looks with dresses and shorts. Any advice, dear readers?

I love this look from J.Crew: patterned tights with ankle boots. But why is J.Crew so expensive? These boots are $250. I mean, really? For J.Crew? Especially in this economy? Don’t get me wrong, the label’s stuff is super cute. But I’ve always found it to be unnecessarily pricey. The tights are $22.50, so not as crazy as the shoes, but I think I would pay that much for tights if I knew they were sturdy. Has anyone worn these before?