Reinvent the Wheelie
Samsonite Black Label
The Vintage 26-inch Spinner Upright was inspired by romantic 1930s travel trunks. samsoniteblacklabel.com, $615.
The zip-up shoe pockets are useful; the cherry-leaf-print lining is just plain fun. orlakiely.com, $350.
Even with three layers of ultra-durable plastic, the T-Tech Polycarbonate Frequent Traveler weighs a mere 8.6 pounds, so you can transport it with ease. tumi.com, $395.
The X2 Flash 22-inch USA is tough enough to go the distance, but carries a lifetime warranty, just in case. titanluggageusa.com, $680.
This Roller Suitcase is equal parts girly (pink-satin lining) and durable (leather trim and laminated canvas exterior). halsea.com, $335.
Dubbed "the world's lightest carry-on" (it weighs in at five pounds), the XCase Exotic comes in 15 designs, like the Orange Flow. ebags.com, $150.
Gilt meets gingham in a piece from Betsey Johnson's accessories line, named for her Mexican vacation home. betseyjohnson.com, $195.
Traveler's Choice Freedom
Target's set includes 21-, 26-, and 30-inch pieces, so you can pick the size that's just right. target.com, set of three $200.