Tops
Shoes
Bottoms and dresses
Outerwear and rain
Accessories
Bags, replacing Kanken and Cabin Zero
Buy in the USA vs wait for Greece
Climate and context
Outfit 1: Athens summer sightseeing
Outfit 2: Island day / ferry
Outfit 3: Rainy Athens winter day
Outfit 4: Mountain day trip, cold
Outfit 5: Smart-casual dinner out
Outfit 6: Minneapolis errands, cold
Outfit 7: New York City sightseeing
Outfit 8: New York smart-casual evening
Outfit 9: Minneapolis winter dinner out
Outfit 10: Travel day, any city
Toiletries and gear
Already owned, just purchased

Traveler Crop Pant (Green/Sage) Eddie Bauer (Costco), owned in XL. 89% poly/11% spandex 4-way stretch, StormRepel water resistant, UPF 50+, 26in inseam - exact inseam match, stretch fabric handles thigh rub far better than the linen pairs that ripped

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High-Waisted Fleece-Lined Legging (Mocha) World of Leggings, $13-24, plus 1X-3X (18W-20W). Full-length, roll or hem to your 26in Buy →

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Bermuda Shorts (Coral Tropics), 8in inseam Old Navy, $18.47 clearance, confirmed to 2X/3X Buy →

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Travel Pant (Black) x2 pairs Kirkland Signature (Costco), owned in XL. 91% nylon/9% elastane 4-way stretch, 27in inseam, back elastic waist, zip utility pocket

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Midi Dress (Navy patterned) B Collection by Bobeau (Costco), owned. 100% polyester, removable belt, functional front buttons

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Bottoms

  • 2 lightweight breathable trousers or chinos
  • 1-2 linen pants
  • 1-2 jeans, at least one cut that dresses up
  • 1-2 shorts, knee-length works better for modesty at sites and churches
  • 2 merino or thermal leggings, for cold and for hiking

Dresses and skirts

  • 2-3 versatile midi dresses in breathable fabric, works for sightseeing through to dinner
  • 1 versatile skirt if you wear them, same logic
unbound-merino-dark-violet-merino-v-neck-t-shirt.jpg

Unbound Merino, dark violet v-neck tee

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Unbound Merino, dark violet long sleeve crew

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Shop (budget)

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Skort (Black), 5in inseam Columbia (Costco), owned. 96% nylon/4% elastane, Omni-Shield water/stain repellent, UPF 50

Already own

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Unbound Merino, navy v-neck tee - merino underperformed in August heat, best for shoulder season

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Unbound Merino, black slim long sleeve v-neck

Unbound Merino, black v-neck tee

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Unbound Merino, sail blue compact travel hoodie

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Quince, ivory cashmere crewneck

Everyday

  • 5-6 short sleeve tees or tanks, breathable cotton or a cotton blend, this is what actually works in peak July/August heat
  • 2-3 linen or linen blend button shirts, doubles as sun cover and smart-casual
  • 3 lightweight long sleeve layering tops

Layering, cold-natured

  • 2 merino wool base layer tops for shoulder season and winter, packs small, regulates temperature. Hesitate to recommend merino for peak mid-summer though, it did not perform well for you in August heat
  • 2-3 medium weight sweaters or knits
  • 1 genuinely warm sweater or fleece for mountain days and indoor winter cold

Athens has a Mediterranean climate. Mild, wet winters and hot, dry summers. Source: Weather Spark, Average Weather in Athens

  • January averages about 8°C, rarely below freezing
  • July and August average 28-29°C, routinely into the mid-30s
  • Most rain falls November through February, December is wettest
  • Summer is nearly rainless

Two things that surprise people moving from the US

  • Greek apartments mostly heat with individual AC units or space heaters, not central heat, so indoors in winter runs colder than the outdoor number suggests. Good indoor layers matter as much as an outdoor coat.
  • Church and monastery visits, common on islands and day trips, usually require covered shoulders and knees. A scarf or light wrap earns its keep.

Fit notes for this board

  • Sizing: tops L / US 14-16, bottoms L-XL / US 16-18 (16 more consistently), inseam 26in. Shop items are checked against this, flagged if a brand runs small
  • You are petite. Midi dresses and standard-inseam trousers will likely need hemming, check length before buying when possible
  • Size is in flux (actively losing weight), so favor stretch, wrap-style, and adjustable pieces for anything bought now, hold off on structured fitted pieces until size settles
  • Fair skin that burns easily, the sun hat and sunscreen notes below are not optional extras
  • Budget mode: it will take about 6 months to afford $150+ pieces again, so shop picks below prioritize genuinely cheap options (mostly Amazon Essentials, Old Navy) over quality-first picks for now

How to look put together

  • Repeat 2-3 colors across categories instead of one-off pieces. Black/neutral base with crimson/wine-red and warm terracotta as accents, matching what you already own
  • One elevated piece per outfit does the work, a cardigan over an otherwise plain tee and jeans reads intentional without extra shopping

Already own

(not loving these colors, found them fragile)

Shop (budget)

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Open-Front Cardigan (Burgundy) Eytino, $29.99, acrylic chunky knit, 1X-4X covers US 16-24 Buy →

Worth buying in the US before you go

  • Deodorant or antiperspirant in your preferred formula. US brands run stronger (higher aluminum content) and are harder to find in Greek pharmacies and supermarkets, which lean milder or natural
  • Technical layers in your exact fit. US stores tend to have better plus-size selection and price than Greek retail
  • Shoes and jeans in your exact size. US stores carry a wider range of sizes and widths, worth stocking up while you can try things on easily

Better to buy once you are in Greece

  • Sunscreen. EU sunscreens use UV filters (Mexoryl, Tinosorb) not approved in the US, generally considered better broad UVA protection than US formulas
  • Anything wool or linen, often better quality and price bought locally than imported
  • EU plug adapter, Type C/F, cheap on either side
  • A voltage converter usually is not necessary for modern electronics, check each device rating before assuming
  • Any prescription-adjacent gear you rely on daily, contact lens fittings, current glasses prescription, etc.
  • A travel steamer or wrinkle-release spray if you are packing tight
memeri-wine-red-merino-wool-snood.jpg

Shop

Sunset Hat (Cinnamon) Sunday Afternoons, $46, packable wide brim Buy →

Narrow Small Vintage (Black), cat-eye frame WOWSUN, $14.99, polarized Buy →

  • Wide-brim sun hat, the sun is stronger than Minneapolis prepared you for
  • Good polarized sunglasses, glare off the water is intense on islands
  • 1-2 scarves or light wraps, sun cover, cold layer, and modest dress for churches
lululemon-heathered-mauve-vinyasa-scarf.jpg

Already own

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Skida, Duluth camping field day snow tour neck gaiter

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Vibram, black Five Fingers V-Trek

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Melissinos, Hermes 2 - handmade leather sandal, Monastiraki workshop

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wowsun-black-cateye-sunglasses.jpg

Melissinos, Artemis C13 - handmade leather sandal, small-sizes range

  • 1 pair comfortable walking sneakers with real grip. Athens marble and stone sidewalks get slippery when wet
  • 1 pair quality sandals, worth investing in since you will live in them on islands and summer streets
  • 1 pair closed-toe shoes or light boots that can handle a mountain trail
  • 1 pair smart-casual shoes for dinners and anything dressier
  • 1 pair flip-flops for beaches and ferry showers

Already own

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Xero Shoes, white Alpine snow boot - cold mountain days

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Altra, Gray/Orange Lone Peak 9, size 8.5 - real trail capability, covers the mountain-trail need on its own

  • 1 packable rain shell. Athens winter is genuinely wet, November through February
  • 1 warm coat. A packable down or synthetic-fill jacket layers under the shell
  • 1 light cardigan or denim jacket for spring and fall
  • 1 windproof layer for ferries and island evenings
  • Gloves and a light beanie for winter and mountain trips

Already own

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Patagonia, white Torrentshell 3L rain jacket - covers the rain shell need

Cooler-weather layer covered by owned merino tops + the Patagonia shell, no packable puffer purchase needed unless mountain days run colder than expected

Xero Shoes, sunset coral Prio Neo - everyday walking shoe

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[[Sun hat|cinnamon sun hat]], shop

Smart-casual dinner out Elevated but not fussy

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[[Tectonic backpack|POLO Tectonic]], shop

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[[Cat eye sunglasses|WOWSUN sunglasses]], shop

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[[Wool white torrentshell 3l rain jacket|Patagonia Torrentshell]], own, over

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[[White alpine snow boot|Alpine snow boot]], own

[[Traveler crop pant|Traveler Crop Pant]], own

[[Ivory cashmere crewneck|ivory cashmere]], own, base

eddiebauer-green-traveler-crop-pant.jpg
quince-ivory-cashmere-crewneck.jpg

Rainy Athens winter day Wet, cool, everyday city errands

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[[Kirkland signature womens travel pant|Kirkland Travel Pant]], own

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[[Ivory cashmere crewneck|ivory cashmere]], own

Athens summer sightseeing Hot, dry day walking the city

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[[Sunset coral prio neo|coral Prio Neo]], own

[[Navy merino v neck t shirt|navy merino tee]], own - underperformed in August heat, swap for cotton if you get one

oldnavy-coral-tropics-linen-bermuda-shorts.jpg

[[Bermuda shorts|coral tropics shorts]], shop

Already own

lululemon, heathered mauve Vinyasa scarf - covers church/monastery modesty

Memeri, wine red merino wool snood - cold layer scarf

Fjällräven, Ulvö hip pack large

Nanobag, sling in pixels print

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Nanobag, daypack in blue waves - covers the hike/island daypack need

REALON Scuba Diving Wetsuit Hood, 3mm neoprene Already purchased, $16.99, ordered September 27 2026, arriving October 5-7

A neoprene hood for cold-water snorkeling, kayaking, or swimming, useful for early or late season island swims.

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Neso, beach tote - covers the packable tote/beach bag need

Shop - Greek brand

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TECTONIC - confirmed 17in laptop compartment, fits your 16in MacBook Pro. Converts to briefcase POLO (Greece), EUR62.70 (~$68) Buy →

[[Hermes 2|Melissinos Hermes 2]], own

[[Heathered mauve vinyasa scarf|mauve scarf]], own

Travel day, any city Flying or a long train, comfortable enough to sit for hours, presentable on arrival

Kirkland signature womens travel pant.jpg
unbound-merino-navy-merino-v-neck-t-shirt.jpg
eytino-burgundy-open-front-cardigan.jpg
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[[B collection by bobeau womens midi dress|Midi Dress]], own

quince-ivory-cashmere-crewneck.jpg

[[Ivory cashmere crewneck|ivory cashmere]], own, layer over if cold

xero-shoes-sunset-coral-prio-neo.jpg

[[Sunset coral prio neo|coral Prio Neo]], own

polo-tectonic-17in-laptop-backpack.jpg

[[Tectonic backpack|POLO Tectonic]], shop

lululemon-heathered-mauve-vinyasa-scarf.jpg

[[Kirkland signature womens travel pant|Kirkland Travel Pant]], own

[[Navy merino v neck t shirt|navy merino tee]], own

[[Merino knit cardigan|burgundy cardigan]], shop, layer

[[Kirkland signature womens travel pant|Kirkland Travel Pant]], own

melissinos-hermes-2-leather-sandal.jpg

[[Sail blue compact travel hoodie|sail blue travel hoodie]], own

memeri-wine-red-merino-wool-snood.jpg

[[Wine red merino wool snood|wine-red snood]], own

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[[White alpine snow boot|Alpine snow boot]], own

[[Tectonic backpack|POLO Tectonic]], shop

polo-tectonic-17in-laptop-backpack.jpg

Minneapolis winter dinner out Cold outside, warm restaurant, need a coat that comes off easily

melissinos-hermes-2-leather-sandal.jpg

[[Hermes 2|Melissinos Hermes 2]], own

[[Wine red merino wool snood|wine-red snood]], own

B collection by bobeau womens midi dress.jpg

[[B collection by bobeau womens midi dress|Midi Dress]], own

patagonia-wool-white-torrentshell-3l-rain-jacket.png
eddiebauer-green-traveler-crop-pant.jpg

[[Traveler crop pant|Traveler Crop Pant]], own

unbound-merino-dark-violet-long-sleeve-merino-crew.jpg

[[Dark violet long sleeve merino crew|violet layering top]], own

melissinos-hermes-2-leather-sandal.jpg
wowsun-black-cateye-sunglasses.jpg

[[Wool white torrentshell 3l rain jacket|Patagonia Torrentshell]], own, coat check

[[Hermes 2|Melissinos Hermes 2]], own

[[Cat eye sunglasses|WOWSUN sunglasses]], shop

Minneapolis errands, cold Everyday city cold, car-to-store-to-car plus some walking

eytino-burgundy-open-front-cardigan.jpg

[[Heathered mauve vinyasa scarf|mauve scarf]], own

New York City sightseeing Lots of walking, unpredictable weather, subway in and out

polo-tectonic-17in-laptop-backpack.jpg

[[Tectonic backpack|POLO Tectonic]], shop

[[Merino knit cardigan|burgundy cardigan]], shop, over

melissinos-hermes-2-leather-sandal.jpg

[[Hermes 2|Melissinos Hermes 2]], own

lululemon-heathered-mauve-vinyasa-scarf.jpg

New York smart-casual evening Dinner and a show, dressier without being fussy

Kirkland signature womens travel pant.jpg
unbound-merino-sail-blue-compact-travel-hoodie.jpg
memeri-wine-red-merino-wool-snood.jpg
neso-beach-tote.jpg

[[Beach tote|Neso beach tote]], own

wowsun-black-cateye-sunglasses.jpg

Mountain day trip, cold Genuinely cold, possible snow, real trail

Kirkland signature womens travel pant.jpg

[[Kirkland signature womens travel pant|Kirkland Travel Pant]], own

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[[Black merino v neck t shirt|black merino tee]], own, base layer

patagonia-wool-white-torrentshell-3l-rain-jacket.png

[[Wool white torrentshell 3l rain jacket|Patagonia Torrentshell]], own, shell

altra-gray-orange-lone-peak-9.png

[[Cat eye sunglasses|WOWSUN sunglasses]], shop

Island day / ferry Breezy, sun-exposed, in and out of water

[[Lone peak 9|Altra Lone Peak 9]], own - real trail shoe

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[[Columbia womens skort|Columbia skort]], own - UPF 50, water-friendly

melissinos-hermes-2-leather-sandal.jpg

[[Hermes 2|Melissinos Hermes 2]], own

memeri-wine-red-merino-wool-snood.jpg

[[Wine red merino wool snood|wine-red snood]], own

unbound-merino-black-merino-v-neck-t-shirt.jpg

[[Black merino v neck t shirt|black merino tee]], own