SIMKHAI says it was founded in 2010 by designer Jonathan Simkhai, whose studio takes inspiration from architects and sculptors. I like that as a packing prompt: a Greece dress should have a shape that can carry an ordinary day, not just earn a place in a photograph. In October, when the trip is still being planned, I would build around the hours I can picture clearly: breakfast, a long walk, and a table after sunset.

THATS SO FETCH's Caryn Dress in white is the uncomplicated choice for the brightest part of that day; I would try it with the sandals I actually plan to walk in, not the pretty pair that stays in the hotel room. Jonathan Simkhai's Stephanie Pleated Poplin Midi Dress gives the suitcase a midi option, and I'd test its stride on stairs before deciding on shoes. Retrofete's Jemma Knit Maxi Dress is the longer silhouette, the one I would save for a slower lunch or a quiet evening. Tanya Taylor's Tay Dress is the wildcard: put it on with two different shoes and see if it earns both a daytime and dinner slot. I would check every hem while moving, and keep the dress that lets me sit, climb, and walk without fuss.

My daytime test is boring on purpose: can I wear the dress for a few hours without thinking about it? Splits59's Ella Airweight Dress reads as the active, easy option by name, so I would reserve it for a day with more walking than stopping. L Space's Steph Dress in Pout-Cream gives the set a soft, light-toned choice; I would check it in daylight and indoors before settling on undergarments. Rebecca Vallance's Lalisa Mini Dress is the shorter silhouette, which makes it a candidate for a lunch where I want room to move and shoes I can walk in. Ronny Kobo's Kallista Dress rounds out the choices without asking the suitcase to be all one length.

The useful question is not which one looks most vacation-ready on a hanger. It is which one works with the shoes already in the case. Try each with the same flat sandal, sit down, take a few stairs, and check whether the hem behaves the way you want. What I would skip: packing two short dresses for the same daytime job if one already feels easy and the other only works with a special shoe. Leave the extra space for a top or layer that changes the mood of a repeat outfit.

A ferry day can change pace, so I would give this group one job: connect the dresses to a cooler-feeling evening without turning the suitcase into a wardrobe for every possible forecast. Rebecca Vallance's Phoenix Rose Long Sleeve Top is the long-sleeved option; I would test it over the bottoms I plan to bring before assigning it a place. Tanya Taylor's Ashby Sweater is the straightforward layer, best chosen only if it can work over more than one outfit. The Rebecca Vallance Nyx Strapless Mini Dress makes a different sort of evening choice, and I would try it seated as well as standing to see if I can relax in it. Veronica Beard's Allora Sequin Midi Skirt is the high-impact separate; a plain top and familiar flats can keep it from requiring a second special occasion.

What I would skip: the Ashby Sweater if the itinerary and forecast give it no real use beyond one imagined chilly night. Pack the layer that has a clear repeat, not the one that solves a hypothetical. Before closing the case, try the Phoenix Rose Long Sleeve Top with the Allora Sequin Midi Skirt and with a daytime bottom. If those combinations feel like two distinct outfits, the top has earned its space.

For dinner, I would choose the feeling first, then stop adding options. THATS SO FETCH's Julia Skirt in white is the separate I would try with a simple top already in the case; if the waistband sits comfortably through a meal, it can repeat without looking like a repeat. Retrofete's Eleanora Sequin Dress is the all-in-one evening answer, useful when I want the dress to do the talking. THATS SO FETCH's Lauren Ruffle Trim Satin Maxi Dress in yellow brings another long option, and I would see whether it works with the same shoes as the white skirt. Jonathan Simkhai's Cris Short Sleeve Shirt Dress is the piece I would test across day and dinner, since the short sleeve and shirt-dress shape suggest an easy change of setting. Simkhai's Vallyn Floral Velvet Mini Dress is a more specific choice by name, and I would not pack it on a trip built around hot afternoons.

The practical test is to lay out the dinner shoes beside each outfit, then remove any look that needs a separate bag, shoe, and underlayer to function. What I would skip: the Vallyn Floral Velvet Mini Dress when the forecast and plan point to heat throughout, or when I already have an evening dress I feel better in. One memorable choice is enough. The rest of the suitcase should make the days easier, not compete with the reservation.

A warm-weather dress earns its space when it can take a change of plans without needing a change of clothes. MANGO's red A-Line Linen Dress has slim straps and a square neck, so I would keep the rest of the outfit plain and let the color do its bit. STAUD's Ayla Linen Midi Sundress uses Porto Stripe, with adjustable straps and a smocked waist that makes the fit feel less fixed. Rails' espresso Avianna Plunge Neck Linen Dress has a deeper neckline and a fluid midi shape, the one I would save for a slower lunch or a late walk. Reiss's neutral Tara Sleeveless Linen Midi Dress adds lapels, on-seam pockets, and an attached tie belt, useful details when I want a little more structure.

Before packing, sit and lift your arms in each one, then check where the straps land under a bag. I would bring the dress that still feels like itself after an ordinary day, not only the one that looks most considered on a hanger.

A cover-up is most useful when it feels comfortable enough to keep on after leaving the beach. Robin Piccone's black Fiona Flouncy Cover-Up Dress has shirring, cap sleeves, and a front tie, so it reads as a light dress rather than just a layer. LSPACE's Misha Smocked Bodice Cover-Up Cotton Maxi Dress brings blue Morning Gingham, adjustable straps, and a smocked bodice in a longer shape. L'AGENCE's black Ansley Paisley Long Sleeve Cover-Up Dress is an open-knit mini with a tied split neckline, which gives it a more evening minded feel. PQ's buttercup Lily Cover-up Dress wraps on quickly for a short stop between the water and a cafe.

What I would skip: a tie or neckline that needs constant fixing when I am carrying a towel and a bag. Try each over the swimsuit you plan to pack, walk around, and sit down before deciding whether it can carry you through a casual lunch too.

The small things in a suitcase should solve a real annoyance, and these pieces each have a clear job. Havaianas' yellow Brazil Logo Sandals are rubber with contrast stripes and an open toe, a cheerful choice for a beach day when I do not want to think about leather near the water. Ancient Greek Sandals' black Eleftheria Sandals are cowhide slides with leather soles, a neater option for dry walks and dinner. Faherty's natural Raffia Sun Hat has a wide brim, so I would try it with the clothes I plan to wear on a ferry rather than assume it fits in every bag. BAGGU's black Cloud Bag is lightweight and packable, expanding when the day calls for more room.

Pack the tote around the hat, then test whether the sandals stay put on your foot as you take a few steps. If a shoe slips or rubs in a short try, a longer island walk will not improve the conversation.

I would pack in this order: decide on the walking outfit, choose one dinner look, then add a layer only if the forecast gives it a job. After that, I would build the repeats around the same comfortable shoes and remove anything that needs a new set of accessories to make sense. The simplest check is to try every outfit once, including the shoes, and ask whether I can sit down, walk a few blocks, and wear it again in a different combination.

Then I would leave a little room rather than filling every corner with a backup dress. A Greece packing list should make the imagined day feel possible, not make me carry six versions of the same evening. I would rather take one dress that behaves from lunch through the late table than bring an entire second itinerary. SIMKHAI's architectural inspiration is a good reminder: a plan needs structure, but the suitcase does not need a blueprint.