My Vacation Packing Guide, Part 2: Harbour Island

I am still recovering from the fact that I packed for a three-day Harbour Island wedding weekend entirely in a carry-on.

To be fair, it was an aggressively swollen carry-on. The kind where you quietly avoid eye contact at boarding because you know the zipper is under emotional stress. But still — no checked bag.

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And honestly, the only reason I pulled it off was because I planned every outfit before the trip.

Not vaguely. Not “these pieces could maybe work together.” I mean actual outfit planning:

• daytime look

• evening look

• which bag

• which jewelry

• which sunglasses

• what shoes

• what could repeat

Because the second you stop planning, you start throwing in “just in case” pieces, and that’s how you end up with six extra dresses and no room for your skincare.

For this trip, I built everything around accessories first – which is almost always how I pack.

I knew I wanted:

• warm cognac suede

• black minimal shoulder bags

• raffia textures

• tortoise sunglasses

• layered gold jewelry

• one standout evening moment

Once I had that direction, the clothing became easy because every outfit lived in the same visual world.

The biggest space-saving trick is repetition.

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The same few sunglasses worked with every single look.
The same jewelry layered through day and night, swapping out a few key items here and there.
The same sandals rotated across multiple outfits.
And the bags became the “personality shift” between looks.

That’s what made the carry-on possible.

For the first daytime look, I packed the ivory knit set because it worked immediately after travel: comfortable, breathable, and polished without trying too hard.

The cognac suede shoulder bag completely changed the feel of the outfit. Without it, the look leaned overly soft. The warmth of the suede gave it dimension and made it feel grounded.

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I also loved that the bag itself packed flat-ish, which became an important theme in my suitcase strategy.

Structured bags are beautiful, but vacation packing rewards flexibility.

That night, I changed into the black asymmetrical mini with the raffia clutch and oversized tortoise chain handle.

This is exactly why I plan outfits beforehand: the dress itself took up almost no room, but because I already knew the accessories would carry the look, I didn’t need multiple evening options.

The raffia texture made the outfit feel island-appropriate instead of overly formal, and the resin chain acted almost like jewelry.

A simple earring and arm cuff completed the look and offered a refreshing new item to focus on.

Daytime on Harbour Island is deceptively hot, so lightweight separates became essential.

The striped knit shorts and cropped black tank were probably the hardest-working pieces I packed because they felt relaxed enough for daytime but still styled.

I paired them with the tiny black shoulder bag because I wanted something minimal that wouldn’t compete with the texture in the shorts.

Tiny bags are secretly the MVP of carry-on packing because they force editing. If a bag only holds four things, you suddenly realize you only need four things.

For the wedding evening, I packed one dramatic option only:
the gold sequin gown.

No backup dress.
No second-guessing.

That’s another carry-on rule:
commit.

The dress was impactful enough on its own that I kept everything else understated — simple sandals, minimal jewelry, natural hair.

And because it was a column silhouette without heavy structure, it actually folded surprisingly well in the suitcase.

No iron required!

By the final day, I wanted the easiest version of dressing possible.

The crochet skirt with the oversized cream tee felt relaxed and effortless in the best way – slightly undone, breathable, and perfect for a slow final morning.

The shell bag was the fun accessory moment that made the outfit feel vacation-specific without crossing into novelty.

I think that’s the balance I’m always trying to find when I travel:
pieces that feel connected to the destination while still feeling like me.

Honestly, this trip reminded me that successful packing has very little to do with bringing less and everything to do with planning better.

What helped most:

• choosing one cohesive color palette

• repeating accessories

• packing lightweight fabrics

• bringing only one real “statement” evening look

• selecting bags that packed efficiently

• pre-planning every outfit ahead of time

Because once every piece already has a purpose, you stop overpacking.

And while the carry-on did technically zip… I would describe the situation as “barely compliant.”