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Southwest Airline Carry-on Policy

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I understand that Southwest allow me to bring 1 carry-on luggage + 1 personal item. I'm planning to bring one backpack with my ukulele strap to one side, a small camera bag (Panasonic Lumix GF3) across my body or around my neck, and a paper bag filled with a few pairs of shoes (probably 2-3 pairs) in my hand. I was hoping to get away with it since Southwest's policy states that wearable articles of clothing does not count as carry-on, and my personal items are small and manageable. Will I be allowed to enter the boarding gate, or will I be confronted before boarding?

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