BrOTP

"I'm telling you, Richard, it felt so real, I could feel the warm wind on my face and the invigorating smell of the ocean. The sun was shining bright and warm, and suddenly I felt so tranquil, as if I had left this world and all it's petty problems behind me..."
"Randolph, my dear friend, I'll have what you're having before you go to bed, if you don't mind me saying."

Richard Pickman and Randolph Carter - the early years.

'The Dream-Quest of Unknown Kadath' reveals that these two used to know each other before Pickman's disappearance. My headcanon - they studied in Miskatonic University together, and while they weren't roommates (both are local boys, so each has a home in Arkham) or in the same courses, their circles more or less overlapped. Both were known weirdos, what with Randolph and his lucid dreams and Richard and his fascination with the macabre, so they quickly became friends.

Although sheltered and somewhat spoiled, Carter's penchant for adventure already shows, what with the practical satchel, the comfortable leather gloves and the unruly hair. His smile is already his best feature and it will go on to win him many friends in many worlds.

Pickman is covered in paint as usual, his scarf is tied in an unconventional way that would make most modern hipsters green with envy, and his hair is composed of several cowlicks that formed a club. The hat he wears will still be seen perched on his head years later, when he's no longer a quirky young lad but a sinister figure, veiled in myth and speculation.