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How to Wear Over the Knee Boots

boots // dress // jacket // c/o Digerolamo bag // sunnies (similar)

Want instantly longer legs? Then you need a pair of over the knee boots in your life.

Over the knee boots have been super trendy for the past couple of years, and if you have not hopped on the bandwagon yet, you should. This style is here to stay for two reasons: 1) You look like you have legs for days; and 2) They can turn any skirt into a cozy (and practical) winter outfit.

Over the knee boots work great with pants, however, I think the best way to really elongate your limbs, is to pair them with a skirt or dress that hits just above the boots (or even kisses the top). This keeps over the knee boots from looking too Pretty Woman, while adding just a hint of sexy. The goal is appropriate sexy. I don’t love the look with mini skirts because (I think) it starts to look less classy and more trashy (for daytime or more professional settings).

Two winters ago in Florence, I purchased my first pair of over the knee boots. They are black Florentine leather and they have proven to be one of my all-time best purchases. I wore them all over Europe and they kept me toasty warm, even in freezing Vienna. This season, I wanted to try something new. So, I opted for a gray suede pair by Marc Fisher. I love the pointed toe on these. It only amplifies the legs for days look, which is a miracle because I am quite short! The soft suede is super comfortable and the back tie helps them stay up (although I recommend wearing socks so you aren’t pulling at your boots all day). That said, they are just as cute a little slouchy.

I will admit that before purchasing, I tried on the infamous Stuart Weitzman version (actually versions, I tried on several), and while they are super flattering and comfortable, I would argue they were not more comfortable or flattering than this Marc Fisher pair. Now, you know I am not against designer items or investing in quality, but once I found this gray pair, I couldn’t justify the Stuart Weitzman price tag.

At first I was nervous about styling grey boots and if I would have enough to wear them with. But, grey is a neutral and I have had zero problems. In fact, they add a little something special to almost any outfit. If you already have and love black over the knee boots, I encourage you to take the grey plunge. You won’t regret it!

I have rounded up some of my favorite over the knee boots below at every price point!