Other Foods that Raise HDL Cholesterol. Foods that are high in soluble fiber, such as flax seed, apples, oranges, and soybeans may help boost your HDL levels. Having a glass of wine with dinner appears to help as well. Olive oil and fish are often cited as foods that help raise HDL levels. However the actual evidence on in this is somewhat weak. But because olive oil and fish oil both have other well-documented benefits, particularly for heart health, I think it’s a great idea to include them in your diet anyway.