Brooklyn Blonde's Balenciaga over-the-knee boots pretty hard lately, so I had a little ShoeDazzle credit and decided to give these a shot. They're surprisingly wearable in real life, not too shiny, and pretty comfortable. I know not everyone is a OTK fan (formerly known as thigh-high and hooker boots, respectively) but I bought my first pair back in 2007 off of eBay. Let's just say...those have gone to a better place now that the more fashionable retailers have started creating over-the-knee looks. They were probably embarrassing, now that I think about it.
1. Nothing shiny. Not only does shiny look cheaper, it translates straight hooker, especially in black! If you're going to choose black, go with suede. It's slouchy-ness will give off a cooler vibe without looking trashy. I love wearing black OTK boots over tights or leggings for a less obvious statement. (these from Asos are pretty inoffensive, here's a cheap version)
2. If you're feeling less adventurous, try a flat one! Flat boots are more versatile and less dressy, so you'll be able to wear them without turning heads (for bad reasons, anyway - combine the rules with this pair!)
3. Pick a color. Black is clearly going to be associated with that Pretty Woman vibe the most, so branch out and look for something in cognac or grey (these are awesome from Macy's!)
4. Finally - things to avoid - too much platform. It might be difficult to find something without a platform right now (they're very on trend) but don't let it creep up too high or you'll be asked where the Champagne Room is. I'd be careful with the heels, too. Nothing too high, too chunky, or too plastic.