TOP: J.CREW STRIPED LINEN BLEND BUTTON UP SHIRT IN RETRO PINK GUARANA COLOR (NOW ON SALE) | SHORTS: J.CREW LINEN BLEND DRAWSTRING SHORT | SHOES: JELLY SHOES | PAREO: PUCCI PAREO ANGOLI COTTON COVER UP VIA MYTHERESA | SHIRT:ZARA OVERSIZED SHIRT | SHOES: TKEES FLIP FLOP | TOP: J.CREW BOYFRIEND JERSEY RELAXED CROPPED T-SHIRT FAVORITE AS SEEN HERE | PANTS: PQ SWIM HIGH WAIST PANTS (THIS YEAR’S VERSION) | NECKLACE: BAUBLEBAR JANETTE | TOP: OLD NAVY OVERSIZED EVERYWEAR TUNIC T-SHIRT ($11.99 RIGHT NOW, COMES IN MANY COLORS, I’M WEARING THE SIZE XS) | SKIRT: STEVE MADDEN VEERA SKIRT IN CLOUD DANCER (SIMILAR COMBO BUT AS A ONE ITEM FROM ENDLESS ROSE MIXED MEDIA T-SHIRT DRESS | EARRINGS: BAUBLEBAR SANTANA SHELL STATEMENT STUD EARRINGS.
Style is a sign of confidence. Not the confidence of always wearing something new, but the confidence of knowing exactly what works — and wearing it without a second thought. That was the idea behind how I packed for seven days in Puglia: one carry-on, a handful of pieces, and the challenge of making each one work morning to night. Not because I had to, but because it’s the kind of styling I actually believe in. Real style isn’t about volume. It’s about knowing what you own well enough to make it stretch.
PAREO: PUCCI PAREO ANGOLI COTTON COVER UP VIA MYTHERESA | SHIRT: ZARA OVERSIZED SHIRT | SHOES: TKEES FLIP FLOP.
The Rule: Every Piece Has to Work Twice
Before packing, every item had to pass one test: could it go from morning to evening without feeling repetitive? A pareo that works as a beach cover-up in the morning can just as easily be tied a different way to turn into a skirt and be perfect for a walk into town later.
TOP: OLD NAVY OVERSIZED EVERYWEAR TUNIC T-SHIRT ($11.99 RIGHT NOW, COMES IN MANY COLORS, I’M WEARING THE SIZE XS) | SKIRT: STEVE MADDEN VEERA SKIRT IN CLOUD DANCER (SIMILAR COMBO BUT AS A ONE ITEM FROM ENDLESS ROSE MIXED MEDIA T-SHIRT DRESS | SHOES: JELLY SHOES | EARRINGS: BAUBLEBAR SANTANA SHELL STATEMENT STUD EARRINGS.
A lace skirt that feels casual paired with a cotton tee at breakfast becomes a completely different outfit with a button-down layered over it for dinner. Nothing in the carry-on was single-purpose. If a piece couldn’t do at least two jobs, it didn’t make the cut. This is the real skill of packing light — not fitting more in, but choosing pieces that were never going to feel like “one outfit” to begin with.
Repetition Isn’t the Enemy
There’s a quiet myth that re-wearing something means you didn’t plan well, or that a wardrobe should always feel new. It’s the opposite. A piece worn five different ways over a week says more about personal style than five entirely different outfits ever could. The pareo showed up on day one and day five, styled differently each time. With a simple white cotton tee, and a beaded necklace, add a hat to protect you from the sun, change it up with a bodysuit to go wine tasting.
TOP: J.CREW BOYFRIEND JERSEY RELAXED CROPPED T-SHIRT FAVORITE AS SEEN HERE | PANTS: PQ SWIM HIGH WAIST PANTS (THIS YEAR’S VERSION) | NECKLACE: BAUBLEBAR JANETTE | SHOES: JELLY SHOES.
The mesh pants did double duty as both a casual summer outfit to stroll around town and a beachside piece. Wearing them again wasn’t a compromise — it was the point. A single well-chosen piece, restyled with intention, does more for your style than an overstuffed suitcase ever will.
What Actually Made the Carry-On
The formula was simple, and it’s the same one I come back to for any trip:
A few foundational pieces — the kind of easy basics that ask nothing of you: a tee, a linen skirt, a pareo.
One or two layering pieces — a button-down shirt, something with a bit more structure, that can be added for evening without needing to change the whole outfit.
A small number of accessories — sandals for day, something a little dressier for night, and one or two pieces of jewelry that pull everything together.
That’s it. No twelve outfits planned to the day. Just pieces flexible enough to be re-combined without ever feeling repeated.
The Bigger Point
Packing this way isn’t really about travel. It’s a small, contained version of how I think about dressing in general — fewer pieces, worn with more intention, styled differently depending on the day and the version of confidence you’re wearing that morning.
Style what you own. Wear it well. Wear it again.