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How does symbolism in design happen?
This is not a researched answer, but I think its likely that women doing this stitching found it more interesting if they based the designs on things that had meaning for them. This would account for why designs that represent the sea and fishing are found on the coastal fishing peoples clothing (diamond waves for example) and designs having to do with crops (plowed fields, windblown grasses) are found on the clothing of the inland farming peoples.
As well as designs symbolizing the natural world and the work their men did, there are the designs that I think come from the domestic cares and work of the women themselves: rice box and steam rising for kitchen work for instance, or tortoise shell as a symbol for good fortune and long life, hemp leaf as a symbol for strong health and connection to community, and bamboo as a symbol for vitality and prosperity.
It is easy to imagine women stitching these designs into garments and household linens as a way to wish these things for their family and friends. A new baby blanket might be stitched with a combination of flax leaf and tortoiseshell to wrap the baby in her hope for strong health, long life, and community, for example. Or perhaps cherry blossoms and the lucky three design would be stitched to wish a girl born in the spring the hope of a good (lucky) future.
Many sashiko designs incorporate several meanings and can be combined to make symbolic messages. Plum blossoms, bamboo and pine bark are often stitched into the same piece to represent triumph over hardship. All three of these are hardy plants that survive the harsh winters to thrive again in the spring, so you might stitch a quilt or jacket or cushion with these designs as a gift for someone who is struggling with hard times to convey hope and faith that they will thrive again.
Most sashiko designs are simple line representations of one or more of three categories: the natural world (plants, animals, the elements), ideas (hope, health, prosperity, fortune, longevity) and the celestial world (blessings). Many combine meanings from more than one of these categories and knowing a little about the symbolism in a sashiko design can make stitching it a richer experience.
A note: There is also a category of design called mons. They are the family crest designs and were sashiko stitched or painted on garments, but they are a subject for another time!