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If art feels like one of those risky acquisitions—no crowdsourcing to fall back on!—start with some entry-level pieces and build your confidence. Hang an oil portrait of a lady and give her whatever personality and history you like. Cheer up a room with a flower painting, interpret (and reinterpret) an abstract, or go for soulful with a landscape or an ocean scene. The only trick to buying art is recognizing what you like.