When I first posted about over the knee boots, the trend was very fringe. Now we’re two years down the line and it’s “the” boot of the season. Mainstream all the way. It always amuses me when that happens, AND how time here on YLF flies.

I was in love with flat over the knee boot styles right from the start and promptly bought a grey pair when we were last in Hong Kong in 2008. I absolutely LOVE wearing them and they became wardrobe workhorses virtually straight away. So much so that I just added another pair to my collection — I nabbed a black Stuart Weitzman pair at this year’s Nordstrom Anniversary Sale and I can’t wait to put them through their paces in cooler weather.

Damona Over the Knee BootsShirley Over the Knee Riding BootsJordon Suede Over the Knee BootsGwenn Over the Knee Platform Boots

I adore the equestrian vibe of over the knee style boots with flat heels – hence the two pairs in my closet. They make my outfits feel pulled together and fashionable, but in a casual and very practical way for our climate and my lifestyle.

I was originally wary of over the knee boot styles with heels, especially with stiletto heels because they somehow looked a little tarty. But after seeing fabulous heeled designs this year with both wedge and stacked heels, I have completely changed my mind. I will personally stick to flats, but I like the aesthetic of heeled over the knee boots just as much.

I vote yay. How about you?