By Kim Taylor

Trekking by plane, cruise ship, train, or rental car? Here are some five-star recommendations for ultimate comfort:

Wear your alma mater, favorite sports team, or most beloved city on your heart, so to speak, with a hoodie from Prep Sportswear. You’re sure to meet more people as a result, and donning it could even spark one of those epic, life-changing airplane conversations. You can flaunt your support for a particular golf course, Greek society, vintage team, destination, government agency — the works. Prep Sportswear even has hoodies, t-shirts, long sleeved shirts and hats from schools overseas. Prep yourself for flight at

You can’t wear slippers to the airport so step into a pair of Keds Rookie Laceless slip-ons instead. They’re every bit as comfy. Who has time for laces? Available in numerous colors and patterns so you can mix and match to suit your style. These are also ideal for schlepping to the pool from your hotel room and back when you don’t want to be seen in the lobby in your flip flops. Easy to kick off and step into, they’re a year-round staple. Find them at

Chooka’s Solid Duck Skimmer slip-on shoes are perfect for rainy destinations, especially warm and tropical ones. They’re lightweight for packing, incredibly comfortable, and fun for splashing around in puddles. They’ll pair well with shorts, skirts, skinny jeans and raincoats. They’ll also be a godsend in the city, year-round. Choose your favorite color at

When you’re sailing the seas and flying the skies – or if you simply want to be comfortable and on-trend – then a boat shoe is practically mandatory. Kohls offers a superb selection of boat shoes for women, men, and children (for everyone on deck) with various styles, colors and labels. Order a pair for everyone at and keep them in mind as Holiday gifts too.

A Sanuk shoe is part sandal, part slipper, part shoe, and incredibly comfortable for beaches, pools, and for running after planes. Available for both women and men, they offer myriad styles and flip-flops too at The Sanuk Chill Collection features boots for winter wear, and the Sidewalk Surfers are perfect for city dwellers who walk dogs and stroll around neighborhoods. Bonus: they offer fleece-lined slippers too.

Arrive at your destination relaxed and ready, as opposed to taxed and aching, so you can forge your own happy trails.

Originally published October 2013
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