I haven’t done a personal fashion post in a very long time. I don’t have a photographer following me around, and when I do… it’s my husband trying to grab a shot while my kids are running towards traffic offscreen (or if I am with friends, I am dragging them off before an event to snap something VERY quickly!).

… but after the EIGHTH girl stopped me on the street in NYC while wearing these boots, I figured I would pick a quiet Sunday morning on this cobblestone street (where cars aren’t allowed), to take a close-up and to discuss the over-the-knee boot trend.

I bought these boots a little more than five years ago. I remember wearing them while pregnant with my son Parker. I was petrified I was making an impulse (pregnancy hormones!) buy… that at the time, could be too trendy. But I was sold for two reasons. An over-the-knee boot with a medium wedge heel (in this particular case), eliminates any over-the-top sexiness while still remaining very playful. And two… the suede keeps any boot a classic.

This particular pair is no longer available (if they were… I’d probably buy two more pairs so I could have them forever!), but I’ve rounded up some styles that have piqued my interest… just in time for the holiday season!

I went with a few Stuart Weitzman options (my originals). Yes, they are an investment piece… but I feel that if you are going to buy this type of shoe, it’s better to buy quality because it shows. Cheap and over-the-knee can read “streetwalker” vs. “street style” a bit too quickly if you know what I mean. The good news? We’ve got Black Friday and Cyber Monday coming up REAL soon, which means you could score some of these at a more digestible price!

The Stuart Weitzman Highline Boot on the left has a higher wedge than mine, but only has a front flap that extends over the knee (which actually makes it easier to pull on). Still “day-time” wearable and I LOVE the praline color!

The Dolce Vita Ashbey Suede Wedge Boot on the right has the same heel height as mine (if that’s what you are looking for), and an ankle strap detail that definitely scores some extra style points. A rubber sole means these boots are made for walkin’!

If a riding boot is more your style, but you want to add a dash more daring to your every day… this over-the-knee silhouette is for you.

The Stuart Weitzman Lowland to the left, and the Stuart Weitzman 5050 Stretch to the right!

… And if you want to throw caution to the wind, and just go all in with an over-the-knee AND a full heel, the Stuart Weitzman Highland and the Sam Edelman Amber Stretch will take you to new heights, and in this case I really feel the suede helps to keep things classy!