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My foolproof accessory math rule (three pairs of shoes, two bags, one scarf/pair of sunglasses/hat each) is especially key for packing for multiple trips. I recommend selecting your shoes before your outfits — a gold pump is perfect for a rehearsal dinner but all wrong for a conference. Shoes can take up the most room in your suitcase. By limiting them to three and planning your outfits around them, you're setting yourself up for carry-on success.