Over 50 and Over-The-Knee Boots? Yes, you can! The OTK Boot has become an accessory that should find its place into every wardrobe — no matter your personal style or age. Since the trend took hold, I’ve added 4 pairs to my wardrobe. My oldest pair is up at our cabin, while the other 3 are in regular rotation in my fall/winter JC/NYC wardrobe. All are Stuart Weitzman, who’s the King of the OTK Boot as far as I’m concerned. While his boots (and shoes) are not cheap, they truly are investment dressing. If well maintained with water/stain protector and professional cleaning and repair, you will have them for many (many!) years to come.