Packing Fall/Winter clothes for a trip isn't a nuisance if you know what pieces to bring. Sure, the clothes are bulkier than your Summer slips and cotton shorts, but the good news is you can rewear certain pieces like jeans and jackets. This cuts down on how many items you have to bring and forces you to pick favorites. We know, it's hard. We find ourselves constantly debating which boot to pack and if we really need six different sweaters.