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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 a portrait of a lady with a large hat and give her a story; cheer up a room with paintings of birds or landscapes, fashion prints or country cottages. Maybe it's a vibrant watercolor of El Torito that floats your boat, or a reclining nude. Get it! The only trick to buying art is recognizing what you like.