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There are a different kinds of boots and different kinds of pants. So it stands to reason that the right hem length for your pants depends on what type of boots and pants you're dealing with. It can be confusing if you don't know a few basic tenets of fashion when it comes to pants length and boots. But, have no fear, it's simpler than it seems.
Wide Leg Length
Wide leg jeans are probably where women mess up the most when it comes to pants length. A pair of flared or wide leg jeans should just graze the floor, regardless of the height of your boot heels. "Graze" means no shorter than 1/2 inch off the ground. If the pants hide your shoes because they're too long, that's just as bad as the pants being too short, so avoid that, too.
Boot Cut Length
Boot cut and straight leg jeans have a little bit more leeway than wide leg pants. The straight shape of the pants has a slimming effect to your calf that lets the pants be a little shorter. If you're wearing flats, the hem needs to at least hit the top of where the sole starts, at the bottom of the shoe's heel. If you're wearing heels, make sure the pants are no shorter than 1 1/2 inches off the ground.
Skinny pants are actually best worn ankle length. You can buy them that way, have them tailored or give them a skinny roll-up until they hit your ankle. These are the most versatile pants because you can wear the same pair with flats and heels, as long as they hit your ankle. Tuck the bottom of your pants into your socks (it sounds dorky, but no one will see), then pull on a pair of knee-high or over-the-knee boots. When the pants are inside your shoes, it doesn't matter how long they are.
Don't think you can get away with one pair of boot cut, straight or wide leg pants if you're planning on wearing them with flats and heels, because you can't. You'll need a pair that's long enough for a heel and short enough for flats. If you want to minimize the number of jeans you own, go ahead and get a great fitting pair of boot cut jeans (they're the most flattering) and wear them with a heel. Stock up on skinnies that can be worn with flats and heels.