When putting on tabi (足袋 split-toe socks), it helps to turn them inside out partway first and then slide your toes in. If you put them on normally, it puts strain on the shiri (尻, the split at the heel of the tabi) and may cause it to tear.
Some people turn them inside out only up to the shiri, while others go as far as the arch; this is largely a matter of preference.
It is said that a neat, slightly snug fit with minimal wrinkles looks chic. In my case, several of my toes have been broken and are misshapen, so tight tabi hurt; I wear a larger size.
To prevent your outfit from coming undone, the general rule in dressing is to put on the tabi first. When putting on hakama, you step in with the left foot first; likewise, you put on the left tabi first. This is sometimes explained as keeping the right side in reserve, though the exact origin is unclear.
