Winter and early spring on Martha’s Vineyard can feel dreamy and reflective: cozy mornings, quiet beaches, cloudy skies. But sometimes? You need a change of scenery. Whether you’re headed to a sunnier coast or just jetting off for a long weekend, the key to traveling well isn’t packing more — it’s packing smarter, cozier, and more stylishly comfortable. Here’s our go-to formula:
The Bag Situation:
🧳 Everyday Carry & Commuter Tote
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Baggu Cloud Tote: This tote is your go-everywhere companion. It’s puffy, lightweight, and spacious enough for your essentials: knit layer, headphones, book, water bottle, sunnies, and that little travel pillow you swear by. Sturdy but soft, it holds up through ferry lines, security checkpoints, and city streets. Reviewers love its easy, packable nature, whether commuting or on the move.
✈️ Main Travel Bag
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Baggu Cloud Carry On: your go-to carry-on when you actually want space. It’s highly rated (from personal experience) for travel capacity and versatility, and it’s roomy enough for multi-day trips without being clunky. It’s especially great if you prefer not to check bags but still want to bring outfits and extras like snacks, an extra pair of shoes, or a knit scarf.
Together, these create a duo that’s functional without ever feeling bulky — and they look just as good on a train platform as they do airline-style overhead bins.
Travel Day Outfit:
Travel days shouldn’t feel like a compromise between comfort and style. They should feel intentional.
🖤 Base Layered Comfort
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Le Bon Shoppe Pointelle Balloon Pants — ultra-soft cotton pointelle makes these the dream pants for travel days. They’re relaxed enough to lounge in but structured enough that you don’t feel like you’re in pajamas at the terminal. The elastic waist, gentle drape, and hidden slit pockets make them truly wearable for planes, trains, and car rides.
Pair them with a matching tee or light sweatshirt, and you’re set for hours of comfort without bulk.
Mix & Match for Destination Arrivals:
Once you land and want to feel pulled together (without a full outfit change):
✨ Swap & Elevate
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Swap the balloon pants for the best-selling Arc Pant — these offer a sleeker silhouette perfect for wandering town centers, cafés, museums, or seaside walks.
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Add a polished top or knit tee you stashed in your carry-on.
🧥 Layer Up With a Jacket
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Polina Chore Barn Jacket: this chore jacket transitions beautifully from travel to exploration. Its versatile structure and neutral tones make it ideal layered over your outfit for brunch, strolls, and early evening wanderings.
🧣 Accessorize
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Pull a cute scarf from your bag (bonus if it doubles as a travel wrap!) to instantly elevate the whole look and add an extra layer when the breeze picks up.
Heading out of winter doesn’t have to mean sacrificing comfort. It means traveling thoughtfully. With a few well-chosen pieces from Conrado, your bag becomes your best travel companion, and every transition! From Vineyard ferry to sunshine or city streets, it feels effortless and intentional. Now get out there and start exploring!
