Packing for a Week-Long Vacation in a Carry-On Suitcase
It's a skill that doesn't happen overnight, but I have several tips (and great pieces to bring)! Checked luggage is simply not worth the stress.
Before you can start packing, you need to know what the heck you own. I clean out my closet every other month. I don't do a full sweep, but I do a thorough job, touching most of my clothes during the process (not accessories; I try to do that 2x a year because that's a whole other beast). If I'm doing a closet sale with a brand, I push myself to get rid of more things, but usually, I have at least a handful of items to donate or sell. I love doing this.
Beyond clearing space and tidying up, the process reminds me of every single article of clothing I own, excites me to wear things I haven't worn in a while, and motivates me to shop for my own wardrobe. I push myself to wear pieces I haven't worn in a while. If I don't wear them by the next clean-out, it's probably time to give them a new home.
This process is also incredibly helpful when it's time to pack. I put outfits together by envisioning them first, often starting with the silhouette type from the Silhouette System™. While I identify as a Palm, I tend to bounce between all three Silhouettes and specifically try to follow the straightforward styling rules of the Cypress when planning what to pack.
I know what I own so well that I can write down outfits suitable for vacation in my Notes App from bed. I'm using my recent trip to Barcelona, Spain, where it climbs about 15 degrees over the course of the day, as an example below. Not so easy to pack for!
My carry-on suitcase is the Away "Bigger Carry-On," and my "personal bag" is a zip-top Baggu bag they don't make anymore. This one from Baggu is similar, and this one from Land's End and this one from Loeffler Randall look a lot like mine. I've tried to get away with chic top-handle bags, but a fabric zip-top is the way to go. It’s so substantial, it's a wonder I have never been stopped for having an entire second suitcase.
Again, I was in Barcelona, where it was 55-70 degrees, which means lots of layering. I wore two outfits daily: one Day outfit for touring and one Evening outfit for dinner.
I acquired new pieces on my trip but never count on that when packing. I like to shop vintage or local in foreign cities and never really know what those items will be.
Tip 1:
Wear layers on the plane. You'll look a bit like a little kid who doesn't know how to dress, but trust me, that cardigan around your waist and the light short jacket under a heavier, longer jacket is worth it when it's "colder than I thought I'd be." Bonus points if the outer jacket has big pockets (like a trench or utility jacket) that are big enough for easy ID/phone access.
Tip 2:
Be smart about your handbags. I brought one that folds up small from Last Frame, in which I stored my electronics, a cylindrical Paco Rabanne one, in which I stored jewelry for travel because it's protective, and a zip-top one with snacks and some beauty products that sat with me on the plane.
Tip 3:
Wear a robe to bed to save space in your suitcase. Pajamas are a waste of space; every item counts!
Tip 4:
If you're packing a blazer (you should!), go for silk, not cotton or wool. Silk packs down so much smaller and is better suited for dressing up your look for dinner — even with jeans!
Tip 5:
Cardigans and vests are great for outfit layering (see Cypress Silhouette layering tips). I wore my cardigan (yes, the one from Gap I recommended here) on the plane, and the two vests I brought packed down very small. ICYMI, I spoke about and styled vests in this week’s Therapy Walk.
Tip 6:
Bottoms are the bulk of my bulk because of my desire to diversify my Silhouettes. Here’s what I packed:
One pair of jeans. You only need one! I suggest dark denim, straight-leg ones. Dark denim is good for dressing up or down, and straight-leg jeans look good with just about any shoe. The ones I brought are from Urban Outfitters and are $59. Always wash dark blue jeans before wearing them to ensure the dye doesn't destroy everything it touches.
One pair of comfy black pants. I prefer cigarette or straight-leg stretch trousers. I could have worn the ones I brought—KULE's City Pant in Black—on the plane. That's how comfortable they are. I wore them day and night because they can be dressed up or down.
One "fun" pair of pants. These weren't necessary, but I am who I am, and I love stripes. These pants from La Veste are also really comfortable for dinner because they fit comfortably.
**Didn't need: One pair of wide-leg trousers. I like these a lot, but they were not necessary. I forced myself to wear them to prove that bringing them wasn't a waste.
One flared midi skirt. Mine is a vintage Lanvin skirt that packs as small as a t-shirt. It has belt loops, too, so it creates the Evergreen drama I want.
One pair of denim shorts. What can I say? I am a Palm! Even though it wasn't quite warm enough for shorts at 9 AM when I left the hotel, I knew I was going on a beach walk and wanted to show off my spray tan, okay?!? These shorts from & Other Stories are THE BEST, with a flared leg and finished hem. They thankfully keep bringing them back, but I've had mine for years.
**Didn't need: One mini skirt. I could have skipped this one because I bought a vintage Fred Perry wrap from Los Feliz, an excellent vintage shop in Barcelona, but again, I had no idea what I would buy, and I love how this pleated khaki one fits.
Tip 7:
Don't pack too many accessories — you won't wear them, and jewelry is so heavy! One or two necklaces, two significantly different belts, and a couple of silk scarves are more than enough! I also brought suspenders, but that’s not for everyone…
Tip 8:
Shoes depend on where you're going, but I suggest one pair of sneakers, one pair of flats (ballet flats are good because they're small, but loafers work, too), and one pair of walkable kitten heels. I wore sneakers most days (we walked 20k+ steps a day), but these ballet flats I link in pretty much every newsletter are so freaking good and under $100. I actually wore them the day I walked the most. The kitten heel slingbacks I wore are the Jack Erwin x Allison Bornstein collab ones from a couple of years ago but linked below are similar good ones! They dress up casual pants to make them nighttime appropriate, and they aren't heavy, so they are carry-on acceptable. I also packed a pair of lace-up sandals because they take up very little space, but I didn't need them.
Tip 9:
I'm saving the best for last as this is my favorite tip, and it's just an item: a 100% cotton striped button-down shirt. Why striped? The stripes camouflage the wrinkles from packing. I packed two, both from KULE. One has thick light blue stripes, and one has skinny brown. I think I wore the brown striped one six times. Striped shirts are good as a base layer, the middle layer in your "outfit sandwich" (again, see Cypress Silhouette layering tips), or even as the outer layer on warmer days!
To be honest, I am still learning the best ways to pack, which will likely keep changing as my style evolves! Maybe someday I will realize that unless it’s 80 degrees, you do not need to bring shorts. But at least I didn’t pack a Ziplock bag of thirteen belts like I did when I was a kid (true story).
I hope you have a fun trip planned for which you can use these carry-on tips.
xo
Eliz
Loved this post! I clicked on the link to your Stine Goya top and wanted to check if you’ve ever ordered from that website?
I love this!