Booties in countless styles, colours and heel heights (I include shooties and ankle boots in the “bootie” category), have been extremely popular in the fashion and style world over the last couple of years. And I don’t see this trend slowing down any time soon. Ladies are pairing booties with EVERYTHING from tapered trousers, cropped pants, classic slacks, skinnies, culottes and jeans, to dresses, short shorts, harem pants, micro minis, bermuda shorts, midis and knee-length skirts. The fashion world is definitely in the midst of a “Bootie Era”. 

As mainstream as they are, wearing booties with skirts and dresses is still considered an edgy, and even unattractive, combination. Especially when you leave off the hose. Several of my clients still prefer to pair skirts and dresses with knee-high boots or pumps because that combination is more elongating and therefore more flattering. To their eye, the horizontally cutting high vamp of the bootie just doesn’t work with bottoms that expose a portion of the leg.

Two years ago I set out guidelines on how to wear booties with skirts and dresses and more recently included midis into the bootie mix. I also included the combination as a way to liven up your work wardrobe. Clearly, I very much support these outfit combinations because the effect looks fresh, spunky and fashion forward to my eye. Since booties became mainstream I have been suggesting the combination to all my clients, just to change up their outfits. This year in particular there has been more love for the combination, which I attribute to “getting used to the look”.

Do you wear booties with skirts and dresses? Did you need a little time to get used to the pairing?  Can the combination look fabulous, or do you feel that when given the choice, knee-high boots and pumps are always a better pairing with skirts and dresses.