Stash your phone, keys, watch and belt in your carry-on before getting into line. After showing your ID, place it back in your wallet and put it in the bag as well. Then place your bag on the belt first, followed by your shoes, toiletries and laptop. Your bag will be out first—making it easier to refill on the other side.

A pair of rubber-soled leather loafers are easy to slip on and off (both at security and on the plane) and can be dressed up or down—whether you're sightseeing or going to dinner.

Bleaker loafer, $109, by Bass

To make packing less of a headache, we suggest keeping a kit ready-stocked with travel-sized products. Order up your favorites from 3floz.com or use GoToobs (right), refillable spill-proof silicone containers.

Stick to one color story for a trip and be amazed at how easy it is to mix and match multiple pieces. If you're not a master folder, embrace the roll. Roll jeans and washed button-down shirts. Stuff rolled socks and ties into shoes and use rolled undershirts and boxers to fill in all available space in your suitcase. Finish by packing your folded jacket or suit on top.

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