This is the single biggest reason women give up on compression socks, and it is almost always technique rather than the sock. If you are trying to pull them on like a regular sock, they will fight you.
Roll them on. Do not pull them on.
The method
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Do it first thing
Before you get out of bed if you can, and definitely before you have been on your feet. Your legs are at their smallest in the morning and the sock goes on far more easily.
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Turn the sock inside out down to the heel
Reach inside, grab the heel, and pull the leg of the sock back through itself so you are left with a short cup with the heel at the bottom.
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Ease your foot in
Get your toes and heel seated properly. This is the part worth taking your time over. If the heel is in the wrong place, nothing above it will sit right.
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Roll it up your leg
Use your palms, not your fingertips, and roll the fabric upward rather than tugging at the top. Work your way up in a few short movements.
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Smooth out the wrinkles
Run your hands up the sock. Creases create pressure points, and a folded band behind the knee is what causes marks.
Things that make it easier
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Sit on the edge of the bed rather than bending over standing up.
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Cross one ankle over the opposite knee if you can still do that comfortably. It brings your foot to you instead of you going to your foot.
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Rubber washing-up gloves give you grip and let you use less force. This is what nurses do.
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Dry skin only. Do not do this straight out of the shower or after lotion. Damp skin makes it much harder.
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Sit against a wall or headboard for support if bending forward makes you lightheaded.
Taking them off
Reverse it. Roll the top down toward your ankle rather than pulling at the toe. Peeling from the top is far easier than dragging from the bottom.
If you genuinely cannot reach your feet in the third trimester, you are not doing anything wrong. Ask your partner, or put them on while sitting with your foot up on a low stool. A sock donner from a pharmacy also works and costs very little.
