Buenos Aires, Argentina
LaCrosse Alpha Deck Foot, $120
September ushers in spring in Argentina, which means less frigid days coupled with moderate rain. The Alpha Deck boots are built with hand-laid premium, natural rubber over insulating neoprene for durability, flexibility, and—most importantly—complete waterproof protection. Its slip-resistant outsole is designed to provide traction in wet environments. So go out with your Yerba Mate, as the handsome model demonstrates here, without a worry that your feet will get soaked.
Reykjavik, Iceland
Cole Haan American Classics Penny Loafer, $158
This September, pack your bags for Reykjavik, Iceland’s capital. With scientists anticipating heightened solar activity this year, you have a much higher chance to view the semi-elusive Northern Lights once it starts getting darker sooner. During the day though, visit Reykjavik’s museums (including the, um, cheeky phallological museum), geothermal pools, and the annual international film festival.
A pair of sensible shoes, like this penny loafer, will take you from a stroll in the city to a gastronomic evening in a restaurant. Wear it sockless or with no-shows.
Styled with: Ortovox Civetta Jacket ($315, ortovox.com)
This smart jacket combines the waterproofing qualities of a hardshell with the breathability of a windbreaker—useful whenever showers are in the forecast. It stows completely in its own pocket.
Antler Large Carry-On – Icon Stripe ($285, antler.com)
This hardwearing and water-resistant shell luggage is crafted from high-quality recycled polycarbonate that’s meant to keep your stuff secure when going through the airport and once you place it in the plane’s overhead compartment.
Toulouse, France
Joseph Leather Sandal, $140
With their rugged design and a midsole that offers lasting cushioning, Danner’s Joseph Leather Sandals offer the ideal mix between form and function—the ideal footwear for a trip to la Ville Rose (the Pink City). With the heritage styling comes a magnetic buckle for easy on and off, a Vibram Traction Cascade outsole for optimal traction on any surface, and a padded heel strap for added comfort. Wear them for a leisurely stroll at the city’s Place du Capitole, a moment of repose at Jacobins Convent, and as you admire the lights from a riverboat at the Garonne.
Rio de Janeiro, Brazil
Havaianas Brazil Flip-Flop, $26
It’s a tad expected, but you’ll be remiss if you stroll the vibrant streets of Rio de Janeiro not wearing the country’s iconic flip-flops brand. The Brazil Logo flip-flop features a cushioned footbed with a textured rice pattern for comfort not usually found in other rubber sandals.
Panamá City, Panama
Vasque Re:connect NOW GORE-TEX, $210
A quick five- to six-hour flight from many US airports is an urban Central American city that’s brimming with history and local color. Besides the iconic Panamá Canal (check out the guide to the Miraflores Visitor Center here), Panamá is also the location of the Metropolitan Natural Park, a 573-acre sanctuary that’s home to hundreds of avian, mammalian, reptilian, and amphibian species.
For hiking and urban trekking enthusiasts, the wildlife preserve has five trails of varying difficulty. No matter which one you choose, lace up with these Re:connect NOW GORE-TEX shoes. Designed for versatile, everyday use, they feature a recycled ripstop mesh upper and GORE-TEX Invisible Fit for waterproofing and breathable comfort. The high-energy return EVA midsole and footbed offer enhanced cushioning and micro multi-directional traction for any terrain.
Styled with: Exped Splash 15 ($39.95, expedusa.com)
This versatile day slash hiking pack weighs only 3.7 ounces but you can take up to 15 liters of stuff with you. Its rolltop closure guarantees that the contents remain dry—as long as you don’t submerge the bag.
Pittsburgh, PA
Adidas Swift Run 1.0, $80
The second largest city in the Keystone state comes alive in the fall, with events sprouting up everywhere as soon as the leaves start to change. Some highlights include the free Miller Lite Thunder Thursdays Summer Music Series, ghost tours, and at least four cultural and food festivals (Pittsburgh Irish Festival, Pittsburgh Soul Food Festival, The Original Pittsburgh Taco Festival, and the Pittsburgh Chinese Cultural Festival).
Model: Nick Henderson, @nickhenderson8
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