Ah, the age-old quest for a perfect pair of thigh-high boots. As we know, perfection can be a tall order (pun intended). A number of boxes need to be checked off: You want ones that don’t slide down the leg, as nothing is more annoying than constantly hiking up your boots as you walk. Then again, they also need to come off easily (it once took three people to get a pair of Louboutin boots off my friend Cindy). They should be slimming. And the right pair do not make one look like a streetwalker while walking down the street. Think chic and sexy, not freaky and sexed-up.
1. Stuart Weitzman Highland Over-the-Knee Boot: There is something so effortlessly seductive about an all-suede boot that hugs you almost all the way up your legs. Especially in buttery soft taupe. At Neiman Marcus for $785.
2. MARC by Marc Jacobs Motorcycle Over-the-Knee Boots: Calling all girls who want to kick some butt (or at least look like they do). MARC by Marc’s biker-inspired pair, complete with trapunto-stitch paneling, will look even better all beaten up. At Neiman Marcus for $598.
3. Chelsea Paris Narumi Over-the-Knee Boots: Think of these as your instant urban armor. The deep side cutouts don’t just look striking. They mean the boots will stay roomy yet stiff and structured all the way past your knee. At Barneys New York for $895.
4. Gianvito Rossi Osaka Suede Over-the-Knee Boots: Part-suede, part-leather, and all-out sensuousness. What I love most about this pair is the fact that you can completely change the look by choosing to fold the top for a cuffed look or pull it all the way up for more coverage. On My Theresa for $1,895.