Fall Road Trip Packing Guide


“I’m a gypsy at heart, and I’ve always been a gypsy at heart.” ~ Diane Von Furstenberg

As the summer is fading away, another August moon, another golden dream drifting away - the heat waves floating into the atmosphere I find I'm thinking about fall road trips, late nights by a camp fire and cozy afghans made by someone's grandmother.

I love a little gypsy adventure... water fall jumping, late night beach swimming, and winding along a country road.

If you’re planning a little fall getaway too, I’m here to help make the packing easy. I’ve been living by this packing guide below, and I find when I add to it too much I end up going back to the essentials anyways. So, might as well keep it simple. To get started pull out your largest duffle bag, a weekender and a cross body bag or back pack. This combination allows for the maximization of trunk space and will tuck easily around the rest of your gear. You’ll want the room for the fun stuff – picnic baskets and piles of patchwork blankets (if you’re heading to colder climates you’ll need extras to stay warm, heading to the warmer locations – you’ll  need extras to build beach teepees).

Of course you’ll also want to leave space for your coolest friend’s traveling vinyl collection – always make sure to invite that friend.

 Whether you’re intending to stay at hotels, hostels or AirBNBs pack the weekender with the intention of carrying it in as your overnight bag; that bag’s job is to move easily from location to location while leaving the rest of your stash in the trunk overnight. If you're on a real deal road trip you won’t likely stay in one place for more than a night or two so lugging a massive structured suitcase around isn’t efficient.   If you make friends out there, having the flexibility to move from place to place will make that free spirited approach, well - actually, freeing. Rotate out what stays in your main large duffle bag, and keep the weekender organized so outfits can be switched in and out.

Here's my favorites.


 If you’ll be leaving bags in the trunk overnight, it goes without saying make sure you park your car in a safe spot and bring any valuables with you in your tent, hostel, hotel or wherever you’re laying your head. Keep the separate, cross body bag or backpack handy and packed with the things you’ll need en route and day-to-day.

Once you’ve got your bags picked out it’s time to get packing. I love this quote from Amanda Brooke’s book I Love Your Style:

“Dad would mix a Mexican tunic and Birkenstocks with chic, center pleated khaki pants and a gold Rolex.”

Knowing what makes you, well – you is important. Your classic pieces will always be chic!

So let’s start with the T’s.

The quintessential layering piece or worn on it’s own, the basic cotton T-shirt can be worn every single day in a variety of ways. Dress it down with a pair of cut-offs or up with a glamorous maxi skirt. No matter where you are on the road, no matter the climate, keeping a stock of your favorite T’s is key. You can’t ever have enough of the plain T variety, however, the collectible T’s (of the band or vintage variety) create a special personal feel.

Rock T’s

Vintage T’s

Muscle T’s

Tanks and Crops

Basically: all the T’s

Next up. Denim.

The ultimate classic: invest in good denim or vintage denim. Light wash or dark wash, or somewhere in between, form fitting denim is always in style.


Hip Huggers

Bell Bottoms



Also on the essentials list, shorts.

They can be layered over tights and leggings in colder climates – and these styles are all you’ll need.

Cut Offs


Embroidered Cotton


 If you own gym shorts, you won’t need them. On the gypsy road trip your gym will be yoga on the seaside, rock climbing in the Rockies, dancing in the desert… you get the idea.

Once your bag is all set with the essentials it’s time to add the fun stuff! Accessories and boots and a gypsy traveling library too. I’ve got those recommendations coming later this week!




Andi Eaton

Andi Eaton is a creative director, author, entrepreneur, and cultural influencer in a variety of media. She produces Oui We (ouiwegirl.com) the modern bohemian's guide to everything from travel and style to beauty and holistic wellness. Andi and her projects have been featured on Domino, Glitter Guide, A Beautiful Mess, Southern Living, SELF, Hello Giggles, Refinery 29, WWD, Elle Canada and more; in 2017 she wrapped a year of road tripping throughout the U.S. photographing and documenting travel, style and culture stories available in her new book: "Wanderful: The Modern Bohemian's Guide to Traveling in Style".