Benable — create shareable lists of things you recommend!
E.g., products you love, local businesses, travel recs - you can add anything to a Benable list!
Cozy Layers for Island Weather (Fall Edition)
14
items What I actually wear when the islands cool down but it's still sunny enough for a coffee outside. No suitcase overpacking required.
This is the piece that saves every shoulder season trip. Warm enough for a breezy evening walk, light enough that you're not sweating the second the sun comes out. I fold mine flat and it barely takes up room in my bag.
Our Iconic Trench Coats
My actual favorite thing to throw on over a sundress once the sun starts dropping. Oversized, soft, looks intentional even when you just grabbed it off a chair. This is the one people always ask me about.
Free People Chunky Cardigan
The holy grail of fall travel shoes. Sturdy enough for cobblestones, cute enough for dinner, and they don't eat up half my suitcase like regular boots do. Life changing for anyone who's tried to pack normal boots before.
Women's Ankle Boots & Booties
Not bulky, not itchy, just quietly warm under a jacket or on its own on a cooler evening. This is the sweater doing the actual thermal work while everything else just looks good.
Women's Merino Wool Jumpers | UNIQLO EU
Packs into its own pocket and takes up almost no space, but it's saved me on more than one unexpectedly cold evening out. Cheap insurance for your suitcase.
Packable Down Vests For Women
Does double duty as a blanket on chilly flights and a styling trick when your outfit needs one more layer of interest. I never travel without one now, it's basically my security blanket at this point.
Oversized Scarf
The layer I throw on over everything the second the sun dips. Goes with literally every outfit in this whole list, which is exactly why I never leave home without one.
Denim Shacket
This is the one item I never regret packing and always regret forgetting. Blocks wind, blocks rain, folds down to nothing in your bag. Boring to shop for, but it saves every trip.
Women's Antora Rain Jacket
This lives under my jacket on windy ferry rides and cool mornings. Warm without being bulky, and it somehow goes with every single outfit in this whole list.
Womens Therma-FIT Half Zip Shirts
Learned this the hard way after a normal umbrella flipped inside out on me in Santorini. This one actually survives real wind, and it fits in the side pocket of any bag.
Windproof Travel Umbrella - Compact & Durable
Swapped my regular boots for a waterproof pair after one too many surprise showers ruined suede. These handle wet cobblestones without missing a beat and still look put together.
SOREL Emelie Chelsea boots | Black
Small thing, but it makes a huge difference on a breezy coastal walk. I keep this rolled up in my bag from October through the whole rest of fall.
Close-Fit Wool-Blend Ribbed Knit Beanie | Men's Hats
My rain day swap for the structured tote. Survives a drizzle without soaking through, and it folds flat when I'm not using it, so it earns its spot in my suitcase easily.
Packable Tote Bag With Zipper
The tiny accessory nobody thinks to pack until their hands are freezing on a boat ride. These are thin enough to still use your phone, which is honestly the whole point.
The North Face Etip Liner Glove, Black, XS