As we roll into the weekend and start dreaming about summer adventures, I’m excited to share the fifth and final part of my Vacation Style Guide series. This time, it’s all about the free spirited, cross country road tripping warrior who hits the highways with confidence and a good dose of style. Road trips have always been close to my heart—they’re a chance to soak in the journey, enjoy the open road, and just take it all in. For me, it’s about traveling comfortably while still feeling put together, and today I’ll walk you through what that looks like, from my own nostalgic memories to the essentials I’d pack now. Whether you’re a road trip veteran or planning your first big drive, this guide’s got something for you. Let’s get started!
I’ve always loved road trips, and that love goes back to my childhood. Growing up, long drives were a regular part of life—hours in the car, cruising down roads I didn’t bother memorizing. I’ve got these vivid mental pictures, and a few actual photos too, of myself back then—sprawled across the backseat, probably grumbling about something trivial like the music or the lack of snacks. As a kid, I didn’t always see the magic in it. The radio would blast songs I didn’t choose, and I’d sit there, half tuned in, half wishing the trip would end. But now, years later, those moments shine bright in my memory. Looking at old pictures, I see a younger me, carefree and unaware of how much I’d come to treasure those days. Life’s shifted since then, with people spread out across the world, and I’m so grateful for those memories—little slices of joy I didn’t fully appreciate at the time.
Those trips were shaped by the 90s, a simpler era for me. My road trip essentials back then were pretty straightforward—earphones hooked to a CD player, since iPods and iPhones weren’t a thing yet. I’d toss in my favorite Nike shoes, a pair of comfy sandals, and a backpack with the basics: a water bottle, sunglasses, and some lip gloss. That was all I needed to feel ready. Kids today seem to pack a whole different game—I picture them lugging bags just for makeup or tech, and it cracks me up. My approach was lighter, easier, and that’s still how I like it. Comfort’s always been the priority, but I’ve learned to weave in a bit of style too, making sure I feel good while I’m at it.
What you pack depends a lot on where you’re at in life, though. Back as a kid, my list was all about keeping myself entertained and cozy. Now, I think about who’s traveling and what they need. If you’re a parent with a baby, for example, your road trip kit might mean three bags of diapers and wipes, and maybe one small one for yourself. But no matter the setup—solo, with a partner, or with little ones—the heart of it stays the same: travel in comfort, look decent doing it, and don’t forget the essentials. For me, that’s always included khakis and shorts—fun, practical favorites that work for almost any stop along the way. And above all, take pictures and have fun. That’s the real point of the adventure.
Summer’s the perfect season for this kind of trip. The weather’s warm, the days are long, and there’s this itch to get out and enjoy it. Flying off to faraway places is great, but sometimes you just want to hit the road, no airports needed. A spontaneous cross country drive—destination anywhere—can scratch that travel itch in a way nothing else does. Before you gas up and go, though, there are a few must haves to make it smooth and stylish, especially for us ladies. I’ve pulled together some ideas from my own experiences and what I’d pack today, so let’s break it down for the road trip warrior in all of us.
Looking back, those childhood rides taught me a lot about what matters on the road. I’d lug my CD player everywhere—probably loaded with Spice Girls or Backstreet Boys—because music was my escape from the car’s chatter. The earphones were a lifeline, letting me tune out when I needed to. My Nike sneakers were beat up but comfy, perfect for pit stops or running around gas stations. Sandals came in clutch when it got hot, and that backpack was my survival kit—water to stay hydrated, sunglasses for the glare, lip gloss to feel a little polished. It wasn’t fancy, but it worked, and it’s shaped how I pack now, even if the tools have upgraded.
Fast forward to today, and my road trip style’s evolved. Comfort’s still king, but I’ve added some flair. Khaki shorts are a go to—light, breathable, and they pair with anything. I’d toss in a few loose tees, maybe a tank top or two, all in neutral tones like white or beige that mix and match easy. A lightweight jacket’s a must—roads get chilly at night, especially out west where the desert drops fast. Sneakers are still in the mix, but now they’re sleeker, maybe a white pair that looks good with shorts or a sundress. Sandals stay on the list—flip flops or strappy ones for quick stops—and I’ve swapped the CD player for a phone loaded with playlists and podcasts. The backpack’s upgraded too—bigger, with room for a charger, snacks, and a reusable water bottle, plus those sunglasses and lip gloss I can’t ditch.
Style’s only half the equation, though. A road trip’s about the vibe—freedom, spontaneity, the hum of tires on pavement. I remember those long stretches as a kid, staring out the window at fields or mountains, bored out of my mind. Now, I’d kill for that kind of quiet—no deadlines, just the road ahead. Pictures from back then show me slumped in the seat, headphones on, but they also capture the scenery—blurry shots of trees or gas stations I snapped to pass the time. I wish I’d taken more, because now those images are gold, proof of a life that’s moved on. Today, I’d be snapping everything—the dashboard, the horizon, my shoes on the gravel at some random diner.
Packing light’s a trick I’ve honed over the years. Growing up, I’d overstuff my bag—extra shirts I never wore, books I didn’t read. Now, I keep it tight: a few outfits, versatile pieces, nothing fussy. Khakis and shorts are staples—they’re comfy for sitting hours but look sharp when you stretch your legs. A sundress might sneak in, easy to throw on for a quick dinner stop. Shoes stay simple—sneakers for driving, sandals for airing out. The backpack’s my lifeline still—water’s non negotiable, sunglasses shield the sun, and a small toiletry pouch keeps me fresh. I’d add a hat now too—baseball cap or wide brim, depending on the mood—for those glaring days.
The warrior part comes in when you’re planning the trip itself. Cross country means variety—cities, plains, maybe a detour through a national park. I’ve done drives like that, inspired by those childhood hauls, and it’s a mix of thrill and prep. You need the basics covered—car’s checked, tank’s full, maps or GPS ready—but the fun’s in the unknown. My 90s self didn’t care about that; I’d just sit there, trusting the adults to figure it out. Now, I’d plot a loose route—say, LA to Vegas or Chicago to Nashville—leaving room for stops. A cooler’s a must for snacks and drinks, and a blanket’s handy for impromptu picnics or naps at rest areas.
Nostalgia hits hard when I think about those old trips. I’d groan at the music—some oldies station I didn’t get—but now I’d give anything to hear it again, windows down, wind rushing in. The photos I’ve got are faded, but they show a kid who didn’t know how good she had it—sprawled out, no worries, just along for the ride. Today, I’d curate the soundtrack—maybe some 90s throwbacks mixed with new stuff—and savor every mile. I miss that simplicity, the way time stretched out, and I try to bring it back when I hit the road now. It’s not the same, but it’s close enough to feel that spark.
For the adventurer in me, road trips are about more than getting somewhere—they’re a style statement too. I picture the perfect kit: khaki shorts, a breezy white tee, sneakers or sandals depending on the stop. A denim jacket’s my wildcard—casual but cool, good for layering. Sunglasses are non negotiable—big frames, classic aviators, whatever works—and a crossbody bag keeps my hands free for snapping pics or grabbing coffee. I’d toss in a scarf too—light, colorful, doubles as a headwrap if the wind kicks up. It’s practical but polished, ready for anything from a diner breakfast to a sunset hike.
Kids today might pack different—phone chargers, makeup kits, maybe a whole outfit change per day. I laugh thinking about it, because my 90s self got by with so little. A baby on board flips it again—diapers, bottles, a stroller—but the core stays: comfort, style, fun. I’d tell any road tripper, young or old, to keep it simple but personal. My essentials haven’t strayed far from that backpack days—water, shades, a lip gloss tube—but they’ve grown with me. Now it’s about balancing the ease of then with the flair of now, making sure I’m set for the ride and the stops.
Summer’s the season to make it happen. The heat’s climbing, and that itch to roll out gets stronger. Flying’s fine, but a road trip’s got soul—pavement under you, sky above, no rush. I’d aim anywhere—maybe a loop through the Southwest, hitting deserts and canyons, or a coastal run up the Pacific. The car’s loaded, essentials packed, and style’s on point: khakis, a tank, sneakers, that jacket slung over the seat. Pictures are a must—I’d capture the road signs, the views, the little moments that turn into stories. It’s what I wish I’d done more as a kid, and I’m not missing it now.
Those childhood drives were a slow burn of joy I didn’t clock then. I’d fuss about the music, the heat, the boredom, but the photos tell a different tale—me, messy hair and all, part of something special. Now, I see the gift in it—time unspooling, no screens, just the world outside. I’d pack that spirit today: a playlist I love, clothes I feel good in, a bag with what I need and nothing more. The road’s the same—open, endless—and I’d take it on with a nod to that kid in the backseat, grateful for where she started me.
This guide’s for anyone craving that cross country fix. Grab your khakis, your shorts, your go to shoes—sneakers, sandals, whatever moves you. Pack light but smart—water, shades, a jacket for the chill. Plan loose, leave room for detours, and snap every shot you can. My 90s self had it right in a way—keep it simple, roll with it, enjoy the ride. Summer’s calling, the road’s waiting, and I’m ready to hit it in style. Here’s to the warriors out there—may your trips be comfy, cool, and full of moments you’ll look back on and smile.
