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As the origins of the Dandie Dinmont are unclear and various explanations given, it is difficult to decide where legend ends and reality begins. Some say that the Dandie's long body and short legs resulted by crossing strains of rough-coated Terriers with Dachshunds; others say that rough-coated Terriers were crossed with Otterhounds. The most probable interpretation of the Dandie Dinmont's origin is that it was developed from the native rough-haired Terrier breeds that worked in the hill country along the border between Scotland and England.

What is known is that as far back as the 17th century these dogs were owned by farmers of the border counties and were used to kill the badger, fox and otter. One early owner of the breed was Willy "Piper" Allan, of Holystone, a man who is also credited with developing the Bedlington Terrier. One of Allan's pack of rough-coated, short-legged Terriers, a dog named Hitchem, excited the interest of the Duke of Northumberland who wished to purchase the animal. In spite of the Duke's generous offer of a life rent lease of a farm, however, Allan refused to sell. "Na, na, ma Lord," he said, "keep yer ferum. what wud a piper do wi' a ferum?" After Piper's death in 1704, his sons and grandsons carried on his strain.

These courageous terriers were unknown outside of the border area, until 1814, when Sir Walter Scott published his novel Guy Mannering. Scott patterned one of the characters after James Davidson of Hyndlea, a farmer who maintained a pack of the Terriers. Scott named Davidson "Dandie Dinmont" and, like Davidson, he kept a pack of Terriers, which were named Auld Pepper, Auld Mustard, Young Pepper, Young Mustard, Little Pepper, and Little Mustard. Scott wrote of them: "They fear naething that ever cam we' a hairy skin on't."

The breed, then called the Pepper and Mustard, was soon regarded with favor. Rawdon Lee in the third edition of Modern Dogs, wrote: "the original Dandie Dinmont Terrier stood higher on legs and was shorter in body than the modern article. This may be observed by reference to early pictures of this dog, notably that by Landseer in his well-known portrait of Sir Walter Scott. Here a 'mustard' dog is introduced, said to have been painted from a terrier then at Abbotsford, and which originally came from James Davidson."

By the time of Davidson's death in 1820, the breed had been renamed the Dandie Dinmont. Although classes were provided for Dandies at dog shows as early as 1861, little excitement was generated until the Birmingham Show of 1867. There, the judge refused to award any prizes to Dandies on the grounds that they were "nothing but a bunch of mongrels." Countless letters appeared in The Field elaborating on this theme. Much confusion prevailed as to correct breed points until 1876 when the Dandie Dinmont Terrier Club was formed and a breed standard drawn up and adopted.