At the repair counter

I placed the left boot on the counter while the assistant finished tying a label to another pair. A section of the sole hung loose beneath the heel, while pale scratches crossed the leather at the toe. She held the boot under a lamp and slowly turned it in her hands. After checking the stitching, she wrote a collection date on a tag and fastened it to the laces. Only then did she ask where the path had become difficult.

From the passage, select two words or phrases that show how the left boot has been damaged.