What should frequent travelers consider when buying luggage?

A practical checklist for choosing the right suitcase and the personal item that makes it all feel easier.

Fabric Luggage Cover in The Bigger Carry-On
$70
Fabric Luggage Cover in The Medium
$85
Featherlight Tote in Jet Black
$98
Large Featherlight Backpack in Jet Black
$118
Featherlight Tote in Blush Pink
$98
Large Featherlight Backpack in Blush Pink
$118
Featherlight Overnight Bag in Cherry Red
$128
Large Featherlight Backpack in Camel Brown
$118
Should frequent travelers buy a carry-on or a checked bag first?
What features make a carry-on easier to use in airports?
How important is organization for frequent travelers?
What should you look for in a personal item to pair with a suitcase?
What luggage is best for short business trips?
How do you avoid overpacking when you travel often?