Imaginary Outfits: On the Road

on the road - drifter and the gypsy blog

Warm weather is beckoning us to roll down our car windows, and I know I am certainly daydreaming of a grand road trip up the East Coast and into Canada. Imagine all the scenic stops! Imagine pitching tents and all the sunrises and all the eats! Now, I’ve been camping and on the road enough to know it ain’t all roses (and it can get flat out old fast), but there is nothing like seeing how little you can live on while taking on the wide open world before you for adventures planned and unplanned. Talk about a metaphor for this thing we call life, right?

I know I’m not alone, since Jack Kerouac pounded out an entire book about this great American road trip concept (and thereby created an anthem about finding oneself for the “lost” Beat generation) — so I got to thinking… what should one wear when traipsing along the backroads and highways of towns big and small? Well, here is my round-up.

And if you can’t take a road trip, you can at least read the book (which I recommend ten-times over the movie, by the way). What about you guys? Are you fond of road trips? What are your must haves in travel? And do tell, is Kerouac’s On the Road a favorite of yours or not so much?


– Top / Hackwith Design
– Jeans / Imogene + Willie
– Scarf / DEsilk
– Sunglasses / Anthropologie
– Necklace / Lauren Winter Co.
– Keychain / Shop Lawrence
– Sandals / Nordstrom
– Tote / Everlane

Mary (Imaginary Outfits contributor)

click here for more imaginary outfits!

    2 responses to “Imaginary Outfits: On the Road”

    1. Liz says:

      I went on a roadtrip last summer up the East Coast and into Canada and it was absolutely amazing. We didn’t pitch tents, but we found tiny motels in tiny towns and it was wonderful. I’ve always wanted to read On the Road, but I haven’t gotten around to it yet.

      • Love that Liz! As an East Coaster myself, I am daydreaming all the time of going up the New England coast and into Canada — I’m actually trying to make that happen this summer. Just gotta get that passport renewed first! xoxo

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