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The debate of traveling with a carry-on versus checked luggage can be a difficult one, though one might assume a two-week-long jaunt would make that an easier decision. My recent summer vacation, which spanned three cities and two countries (requiring eight separate flights) over the course of fourteen days, was accompanied by only a jam-packed carry-on suitcase and a packed-to-the-gills duffle bag. I used a rolling technique for my clothes, and utilized every nook and cranny for everything else, resulting in two heavier than necessary bags.
Prior to the trip, I tried on outfits as I usually do, threw some last-minute “just in case” items in (as I usually do), and ultimately ended up overcompensating for the fact I wasn’t checking luggage by overpacking as much as I could into my two cabin sized bags. Despite everything I crammed into them, throughout the trip, there were really only a handful of pieces I wore more than once. Call it a vacation capsule wardrobe, if you will. In hindsight, I should have packed with that strategy in mind and left a lot of the extras behind at home. Here, a report card on the items I wore most, the nice-to-haves, and the pieces that didn’t even make it out of my suitcase.
Most-Worn Winners
Hill House Home Delphine nap skirt
Worn as a beach cover-up, out to lunch and dinner, to walk around small towns, and to hang around the house, this was easily the most worn piece of clothing I brought.
Staud Sea tiered midi-skirt
Banana Republic Laurel skirt
Mango leather sandals with straps
I packed multiple pairs of sandals, from black chunky slides, rope sandals, to colorful strappy lace-ups. These looked and felt the best with everything, from beach day outfits to dinner dresses.
The Row City flip flop sandals
Ancient Greek Sandals Saionara flip flops
Anemos Keaton wide leg pants
I love a tailored trouser or pair of jeans more than the average person, but when you’re hot, sandy, or simply trying to reach a state of full relaxation, there are no better pants to have with you on a summer vacation than one that’s loose, lightweight, and comfortable.
Cuyana linen wide-leg pants
Aexae drawstring trousers
After many summers of experimenting with all types of swimsuit silhouettes in all different colors, a basic black string bikini has always been my go-to. This trip was no different.
Eres Les Essentiels bikini
Loewe x Paula’s Ibiza woven basket bag
Big enough to carry the essentials, sunscreen, sunglasses, wallet, compact, a book, etc. but small enough to appropriately bring along for meals out. I used this practically every day.
DeMellier mini Santorini raffia basket bag
Massimo Dutti mini woven basket bag
Janessa Leone Felix bucket hat
Despite being very annoying to pack, a proper sun hat is crucial, and worth the space it took up.
Lack of Color raffia cowboy hat
Nice to Haves
The Crochet Top
A trend-forward item to mix in with the rest of the mainstays, in a silhouette I love.
The Cord Necklace
I ended up bringing a lot of beachy jewelry accessories, but ultimately I only wore one necklace.
Julietta Mermaid Dreams gold-tone choker
The Going Out Bag
It was fun to have an extra bag to switch up for nighttime; however, it only was used two times. Luckily this one is flat and small, therefore didn’t take up too much space in my suitcase.
Paco Rabanne Nano sparkle bag
The Statement Pant
For the days I wanted a little more style, oomph!
Julietta Mermaid Dreams gold-tone choker
The Beach Short
For casual afternoons at the beach or at breakfast time, a pair of casual shorts acted as a coverup and presentable “pajamas.”
Dôen Blaze ruffled striped shorts
The Tunic Top
I don’t wear dresses much, but sometimes even I just want to wear one piece of clothing. Enter the tunic top. Long enough to wear with nothing on the bottom when worn over a swimsuit, and chic enough to wear as a top over pants. Versatile!
Wore Once... Or Not at All
The “Going Out” Shoe
Unfortunately for me, I packed an old pair of Bottega Veneta wedges, which were bulky and heavy. I ended up carrying them around the entire trip and only wore them once, they probably should have been left behind!
The Just-In-Case Jeans
Before my trip, I was wearing jeans almost every day in New York. After the plane ride over, they didn’t make it out of my suitcase once.
The Extra Swimsuits
I probably squeezed twelve or so swimsuits into my suitcase, realistically, I wore five of them.
The Destination-Appropriate Dress
There are some items in your wardrobe that you think would be perfect for XYZ location, so you hold onto them. Safe to say, even when I was in the right locale for the dress, in the end, I stuck to wearing what made me most comfortable.
