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Stretching is safe and helps mold boots to your foot, but it's no magic wand; some boots are just too small, which is why the fashion fairy has a return policy. Boots that are way too small are an excuse to go shopping, while those that almost fit can be stretched. Calf leather is soft and pliable, and you've got several ways to take advantage of its natural movement to encourage the stretch. Evaluate your boot fit, then get to work, using the best method for your fashion fix.
Stretch out new calf leather boots to remove the stiffness and "wear them in" a bit. If your boots fit your feet but just feel tight, this gives gentle stretching to minimize tightness. Think of it like yoga for your shoes. For a mini-stretch, slip on your bulkiest athletic socks, then put on a second pair. Put the boots on and wear them around your house, and shake your booty to get things working. Spend a weekend walking in your new boots at home and the leather should be stretched enough to make the boots comfortable.
Hang them up if you got boots that are a touch too small for your feet. Get shoe trees or boot trees and place these in your shoes, then let them do their thing. This will cost you -- so maybe you can just return the too-small boots for a size upgrade -- but it will stretch boots that aren't sized right for you.
Help calf leather boots fit your feet, if you have the right size boots but part of the shoe just doesn't fit right. Put on your double layer of athletic socks for this method. Rub a cotton ball moistened with rubbing alcohol over the part of the leather that's a no-go, like your toe or your ankle. Get the inside of the boot, not the outside. Right away, slip your socked-up foot into the boot. Wear the boots for at least half an hour to loosen the stubborn spot and feel comfortable.
Bring the boots to a cobbler if you've tried at-home methods and still feel pain, or if you've been able to stretch some but not enough. While some boots are just too small, a good cobbler can stretch the boot or fit the leather with a patch to make it bigger. If your tall boots dig into your calves, they can elasticize the leather or patch it for a bigger fit.
Think about how much stretch you need before you get started, since you probably won't be able to return a boot that you've stretched out. If you need to exchange the boot instead, be a savvy shopper and go for it.