Outfits That Worked for His Itinerary and Mine

We shared a suitcase. We didn’t share an itinerary.

While he mapped out brewery tours and early morning tee times, I was screenshotting art galleries and vintage shops that didn’t open until noon. Our schedules couldn’t have looked more different on paper, but we somehow made it work — logistically and sartorially.

I packed what I needed for my days, he packed for his, and in between, we ended up borrowing from each other (read: I borrowed from him). One piece in particular — the Rowan Crew Tee by Reformation, in a perfect green-and-white stripe — became the accidental MVP. It started in his packing cube and ended up styled under my linen blazer, then knotted over trousers the next day.

This is what we each wore, what actually worked for both of us, and the small styling overlaps that made me appreciate our wildly different but oddly synced-up travel habits.

The Packing Strategy That (Sort of) United Us

We didn’t plan to coordinate, but we didn’t want to look like we were heading to two different countries either. I packed for the vibe, not the match — and somehow, our pieces ended up speaking the same language.

Coordinated Color Palettes Without Matching Outfits

We somehow landed on a shared color story without discussing it: soft olive, cream, washed navy, and one bold green accent. I think he picked it up from one of my Pinterest boards I left open — not mad about it. It meant I could swap my tan crossbody onto one of his jackets and it still felt intentional.

Planning for Layering, Not Cloning

He packed a canvas overshirt; I packed a trench. Both worked over our basics and ended up layered on each other at least once. I tossed his shirt over my midi dress at the farmer’s market. He threw on my trench when it got breezy at dinner — sleeves too short, but cute in that “I made this work” kind of way.

One Piece We Both Ended Up Wearing

The Rowan Crew Tee by Reformation was never supposed to be shared. It’s cropped on me, standard on him, and for some reason, it worked both ways. The green-and-white stripe gave every outfit a little something without being loud. I wore it under a blazer one day and with linen pants the next. He wore it solo with dark jeans. I wore it more. No apologies.

What I Wore (While He Was at the Brewery Tour)

While he was off rating IPAs, I was browsing bookstores, sipping long coffees, and quietly judging outfits (for research). My looks had to walk a lot, look good in photos, and handle the unexpected.

Linen Pants That Didn’t Wrinkle in the Rental Car

These were the quiet MVP of the trip. High-rise, wide-leg, and lined — which honestly shouldn’t be such a rare combo, but here we are. They held their shape through long drives, squished seats, and way too much sitting. I wore them with sandals for markets, sneakers for walking days, and once with a heeled boot just to feel a little elevated. Zero wrinkles. Zero regrets.

A Top That Dressed Itself Up

My knit tank with a square neckline pulled its weight. It’s the kind of top that looks intentional without needing help — fitted but breathable, slightly structured, and easy to pair with literally anything. On its own, it felt low-effort chic. Tossed under a blazer at dinner, it made me feel like I’d actually planned an outfit (even if I hadn’t).

Accessories That Traveled Light

I brought one soft crossbody in a warm tan with gold hardware, and it worked with everything. No outfit felt too casual or too overdone with it. I stuck to my gold hoops and a pair of matte black sunglasses I never had to baby. The goal: elevate without overthinking — and not once did I wish I packed more.

His Outfits (That I Secretly Rated in My Head)

He doesn’t overthink what he packs — which is impressive and mildly infuriating. Somehow, he still ends up looking effortlessly put together, even if half of it feels accidental. I kept my commentary mostly internal… except for the shorts. You’ll see.

A Polo That Didn’t Look Boring

It was soft, structured, and in a muted clay shade that worked with pretty much everything. He wore it with jeans one night, then with tailored shorts for brunch — both looked great. The collar held its shape, which sounds minor, but makes a difference. I didn’t compliment him out loud until day three. Timing is everything.

The Shorts That Were Not It

I get that they were “comfortable.” I do. But they gave off college-dorm-core energy — lots of pockets, not enough shape. He knows how I feel. I’m not trying to change him, just… nudge gently.

Shoes That Worked for Both Our Schedules

He packed sleek white sneakers that held up from coffee runs to casual dinners. And yes, I stole them one morning when mine were still drying from a surprise downpour. They fit a little big, but the look? Very much approved.

Outfits We Actually Matched (Without Trying)

We didn’t coordinate. Not once. But somehow, a few of our outfits landed in the same visual family — color, texture, vibe. It wasn’t intentional, which honestly made it better. Like when your coffee order accidentally matches your mood.

Dinner Looks That Felt Effortless

One night, he wore a deep navy camp collar shirt over the Rowan Crew Tee and black jeans. I showed up in a black midi with a side slit and tossed his overshirt over my shoulders. We didn’t plan it, but when the host asked if we wanted a photo, I didn’t say no.

Morning Market Outfits

We were both in soft layers — me in linen pants and his tee (again), him in joggers and a beanie I packed. It felt relaxed and quietly pulled together. I blame the muted tones. And the shared caffeine dependency.

Travel Day Uniforms

Black joggers, boxy tees, baseball caps. No conversation needed — we both just showed up like that. It was comfy, airport-approved, and not entirely tragic when we had to sprint for our gate. Bless the stretchy waistband.

What I’d Pack Again — and What I’d Borrow Up Front Next Time

Every trip teaches you something — sometimes about a destination, sometimes about your partner’s wardrobe. This one gave me clarity on both.

Repeat Pieces That Carried Their Weight

There were a few pieces I’d pack again in a heartbeat. My high-rise linen pants were the clear hero — I wore them three times without needing to re-style or even think about steaming. The square-neck knit tank held its own across multiple outfits and moods, proving its worth with zero effort. And then there was the Rowan Crew Tee by Reformation — technically his, but I wore it more. I’ve already added it to my cart (in another color, obviously).

What I’d Leave Behind

There were also a few things I wouldn’t bring again. The platform sandals gave me blisters before we even made it to lunch — they photographed well, but only if you didn’t zoom in on the bandages. One jumpsuit wrinkled faster than it zipped, which made it instantly annoying. And the cargo shorts? Let’s just say they’re not invited on the next trip.

Conclusion: A Striped Tee and a Shared Aesthetic

We didn’t pack for each other. We didn’t dress to match. And yet, somewhere between the gallery mornings and brewery tours, our wardrobes started to blend — just enough to make the trip feel shared.

The best part wasn’t looking coordinated. It was feeling like ourselves, separately and together. I wore what made sense for me, he did the same, and sometimes we landed in the same lane. That green-and-white Rowan Crew Tee by Reformation became the quiet thread tying it all together. It started in his cube, ended up on me, and now lives permanently in both of our mental packing lists.

Next time, I’ll plan less, borrow more, and pack the pieces that let me stretch — in style, in schedule, and in the best kind of shared space.

Style is personal, but good taste speaks loud.