5 Cool People in Their Aspirational Travel Outfits

I GET the appeal of athleisure. I have days where I’m one prom-posal away from wearing white leggings to my own wedding just in case I want to cartwheel down the hypothetical aisle. But when it comes to travel — which is romantic in theory but in reality, the ultimate schlep — wouldn’t it be nice to dress in a way that brings back a bit of pomp and circumstance? At the very least, wouldn’t it be nice to show up at your destination looking already refreshed?

In honor of the holiday weekend at hand and a glorious three-month stretch of summer weekends ahead, I asked five passport-toting travelers for their aspirational travel look. An aspirational travel look is the thing you’d wear if you didn’t have to worry about TSA, luggage fees, missed ferries or crowded trains. Scroll through for their concoctions and then, in the comments, let me know what you’d wear (and where). There’s a lot of days in a summer — let the in-transit outfit inspiration-banking begin!

Ramya Giangola, Founder of Gogoluxe

If we’re talking about the ultimate travel fantasy, then I would already be in Athens for a few days, ready to embark on a month-long Greek island-hopping adventure by sea on a dream yacht.

I am wearing this crisp, gorgeous cotton dress from Colombian designer Silvia Tcherassi because it’s basically like wearing your coziest nightgown. (Also, the anchor print is very much on-theme for the boating experience I am about to have.) It can double as a beach coverup and, of course, it’s great for a night on the town in Paros or Patmos!

This Staud bag is perfect because it’s almost a two-in-one. The netting can be used separately and is perfect for when we stop and go market shopping for provisions to bring back to the boat. These Céline slip-ons are super comfy and work with everything, plus they’re easy to slide on and off.

I kept kept the jewelry minimal but chic: a Céline daisy necklace and a leather charm necklace by RTH.

Last but not least: our dog Nero. Because this is the ultimate fantasy, he would be with me on my Greek adventure.

IG: @gogoluxe

Azède Jean-Pierre, designer

Azede Jean-Pierre shirt dress and pants, ATP Atelier shoes, hat from artisans in Haiti.
Photo by @visualsbypierre.

I’ve been going back and forth from the Caribbean recently to get inspired for my next collection and a few philanthropic projects I’m working on. I like the idea of all-white for travel because it’s refreshing, and it feels like a mental blank canvas keeps you cooler in warmer weather.

The loose fit of this look adds to the overall breathability and comfort, and there’s something bold and confident about these large-sized garments.

IG: @azedejean_pierre

Laurel PantinEditorial and Fashion Director at Coveteur

Lacausa dress, vintage green jacket — another here, Cornetti sandals
Photo by Andee Olson.

This is my best “Upper West Side Mom” outfit (despite the fact that I’m neither a mom nor an Upper West Sider). It’s exactly what I want to wear on my haul out to the Hamptons this weekend. It’s supposed to be rainy and kind of chilly, and this Lacausa dress and vintage green jacket work for my Grey Gardens fantasies. I’ve been wearing these Cornetti sandals everywhere because I love how they sort of disappear into my legs, and because I plan on alternating between this dress and my long-sleeved Sleep Shirt dress all weekend. I’m not bringing a suitcase.

IG: @lapantin

Lucy Laucht, Photographer

I love the concept of dressing up for air travel. It’s a lost art in a world of sweatpants, neck pillows and scratchy socks. Recently, I flew to Rome and this insanely chic lady was on my flight. She wore bright colors in that perfect Italian way and it inspired me to up my game. Practicalities aside, I’d wear this outfit on the plane, hopefully arriving just in time for aperitivo at Hotel Caruso in Ravello.

IG: @lucylaucht

Anum Bashir, Founder of Desert Mannequin

In this look, I’m on a gondola traveling through Venice for the opening of the Biennale this summer. Contemporary art plays a huge role in my life, and both the Biennial and Italy hold a very special place in my heart. It’s where Waqas and I honeymooned back in 2011.

First stop on the itinerary is Lorenzo Quinn’s much talked about installation entitled Support.

Why did I choose to wear this? Because when in Rome (or in this case, Venice). In order to look as quintessentially Italian as possible, I’d turn to Gucci. The goal is to look/feel local (considering their go-big-or-go-home approach to style), eclectic and like a seasoned veteran of the art world. Leggings, sneakers and T-shirts just won’t cut it. This top by Gucci does a great job at saying, “Hi, I’m here in Venice. Do you want to speak to me in Italian and sell me a painting or two?”

IG: @desertmannequin

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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