I went for a very Johnny Depp-esque/ Captain Jack Sparrow look with Pip. Or tried at least.

Pipsqueak did not stay a genuine pipsqueak for long. In truth he is still the shortest stallion in Ponyville, but at least he’s bigger. And he’s learned to utilize his accent and deep voice to woo the mares in town. It works some of the time but over time Pip develops a shorter temper and a potty mouth. He sounds very indignant and somewhat drunk when he gets into a cussing match with whichever blighter picks a fight with him or one of his friends. Boy swears like a sailor.
Speaking of sailors, Pip’s talent is sailing. His cutie mark was originally just the nautical star but he had the sword added in. As well as the anchor on his left shoulder and a swallow on his right. What a bad boy.
By day he’s a shanty singing fisherman’s apprentice and by night he cooks mediocre meals and serves out warm ale to the towns folk and soldiers that pass through.