Admittedly, I'm a real sucker for these sorts of things, but look at how much effort went into that cap and blue wool sailor's suit, and hand-painting the eyelashes on that bright-eyed clothespin face! All he needs is a ship!
I've found some clothespin sailors, but no others quite like him. I'd guess maybe 1940s or so, but am not completely sure. Overall, here's in good shape, with a little wear to the shoulders of his coat. It does appear he was likely once mounted onto a base (or boat) as there is a little torn paper stuck to his feet. Nonetheless, he stands up straight on his own. 4 1/4" t x 1 7/8" across at arms.