What to Wear on a Retro Road Trip

What to Wear on a Retro Road Trip

The road trip is already having a comeback, but throw in a retro twist and suddenly, it’s an experience. There’s something magnetic about stepping into a vintage-style car, gripping the steering wheel, and chasing the horizon like it’s 1972 again, or Thelma & Louise.

Christen and I took our first road trip in the summertime of last year, driving from Ohio to Oklahoma. We went through Indiana, Illinois, Missouri, and Oklahoma on the way there, then Arkansas, Tennessee, Kentucky and Ohio on the way back. It was one of the best trips of my life!

But let’s not forget: the ride is only half the vibe. The look? That’s what seals the deal. It’s for the woman who knows adventure doesn’t mean compromising style. Putting together your amazing outfits for each state, planning photos at some amazing stops… it’s the best thing!

Pulling off a retro road trip outfit doesn’t require a suitcase full of vintage finds or digging through your mum’s old Polaroids though. It’s about finding that sweet spot between nostalgia and now, and dressing like you own every mile of that highway. I can’t wait to go on the next one this summer!

Style in the Driver’s Seat: Dressing for the Vibe

Retro isn’t just a trend. It’s a declaration that comfort and cool can coexist. A good road trip outfit should move with you — out of the car, into diners, through roadside antique stores — without making you feel wrapped in a museum exhibit.

Start with the staples: high-waisted jeans or cutoffs, a knotted crop tee, or a halter that lets the sun do its thing. These pieces don’t just flatter — they breathe. And that matters when you’re clocking hours behind the wheel.

To fully embrace the spirit of the open road, pair your high-waisted denim with stylish Corvette apparel that echoes the boldness of vintage muscle cars. Think iconic logos, old-school energy, and enough punch to match the engine’s roar. I actually even have a cropped tee with a Corvette logo on it! You can see the full Instagram reel here.

Keep it effortless but curated — the kind of look that makes strangers nod and think, “Yeah… they’ve got stories.”

Shoes that Won’t Ruin the Road Trip

A special kind of regret comes from wearing the wrong shoes on a long drive. Don’t be that person blistered up before the first pit stop. That’s a huge no no for me!

Here’s the golden rule: choose shoes to drive in and sprint to the bathroom during a questionable gas station detour. Think platform sneakers, but Low-rise boots with cushy soles are even better. Leather sandals with straps that don’t slice your skin? Perfection.

Leave the heels and anything that requires a breaking-in period at home. Retro can still mean practical. Remember, you’re not strutting a runway — you’re chasing the sunset at 70 miles an hour.

Accessories that Turn Heads at the Gas Station

You don’t need to over-accessorise—just be intentional. The best retro pieces serve double duty. Think cat-eye sunglasses that block the glare and up the glam, or a silky bandana that works as a necktie, hair wrap, or quick windshield wipe when bugs get bold.

Chunky hoops or a stack of bangles make pit stop selfies pop, and if you’re into the ‘70s vibe, throw in some amber-tinted lenses for full-on movie-scene energy.

Tip: Keep your accessories close—literally. Use a small dashboard pouch or belt bag so you’re not fishing through your weekender every time the light hits just right for a photo op. Road trips move fast, and your style should be ready when the camera is.

Layers for Sunset Stops and Unpredictable Weather

Even the sunniest road trips hit a chilly patch. Whether watching the sun dip behind a canyon or fueling up in a gusty parking lot, you’ll want a layer that earns its space in your bag.

Denim jackets are an obvious go-to, but don’t sleep on vintage bombers or varsity cardigans. They add texture and nostalgia without trying too hard.

Stick to neutral colours if your outfit is loud, or go bold if the rest is minimal. The right outer layer doesn’t just keep you warm—it adds story. Like, “Oh, this old jacket? I found it at a flea market off Route 66.”

Let your jacket be the chapter that surprises people mid-scroll on your Instagram carousel.

Gear that Holds Up (and Holds your Stuff)

A retro road trip doesn’t mean lugging around clunky bags that scream 2005. It means thoughtful packing — with style.

Enter: the weekender tote. Canvas, leather, or even upcycled denim. Bonus points if it looks like something Stevie Nicks would’ve thrown into the back of a tour bus.

Crossbody bags with vintage buckles or fringe details are perfect for quick grabs — wallets, chapsticks, and Polaroid. Make sure whatever you bring doesn’t dig into your shoulder or explode open when you slam the brakes for a photo-worthy mural.

You’re chasing vibes, not chasing your earrings under the passenger seat.

When the Destination Demands a Little Something Extra

Every road trip has that moment — a quirky diner glowing in neon, a roadside dance floor, or a scenic overlook where you could end up on someone’s Pinterest board. This is when you level up.

Pack one wild card: a retro dress with a swingy hem, a wide-legged jumpsuit with a halter top, or even a metallic miniskirt if the playlist’s feeling disco-heavy. This is the kind of outfit that makes a short stop feel like an event.

Pair it with a red lip, fresh-from-the-car curls, and a lot of attitude. Trust me — if you’re going to get snapped at a roadside attraction, you’ll want to look like you knew the moment was coming.

Conclusion

A retro road trip isn’t just about the car, the playlist, or the scenery. It’s about how it makes you feel — a little freer, a little louder, a little more like the version of yourself that dances at red lights and orders pie at 2:00 a.m. The right outfit doesn’t just match the mood — it creates it. It lets you show up to every stop, stretch, and scenic view feeling like you’re living inside a mixtape. I can’t wait for the next one!