Granny boots and I have a dramatic relationship. Sometimes we understand each other, but we have a long history of mutual disdain that can sometimes complicate things. I didn’t understand “granny boots” at all for a long time… until I saw them with a really well-fitting pair of cuffed skinny jeans. That was the turning point.
I still think they are unflattering sometimes, but that’s mainly because flat boots are hard to wear with everything – sometimes they look perfect, sometimes they look awful. Heeled boots have the advantage there because… well, they’re heels for God’s sake. Meow.
Granny boots + heels, on the other hand, is a match made in heaven, if you ask me. Especially given that the hell isn’t really dramatic, it makes them more versatile than a conventional heel because, well, the whole able to walk in them thing, mostly.
The Virginia ankle boots from Target are cool because they’re basic, but because of the heel, they become wearable beyond jeans. I would wear these with the right skirt, or dress. Definitely with lazy-person outfits like leggings and a top, or maxi skirts. Also, side-zip bonus! Lacing stuff is for losers!