Hi, holy grail.
I’ve written about packing for a business trip in a handbag. And I’ve written about packing for a weeklong car trip in New England. But a dear friend of mine wants to pack for a week in Italy and Greece in a carryon. So here we go.
I’m going to start with the bags themselves, first.
Pick the biggest carryon the airline will allow. Wheels, obvs. But there are slight variations. Here’s a trick I learned from Trinny Woodall (again). Do an Amazon search for carryon + your airline and you’ll get suitcases that are light and max carryon size. (!)
Also, use the biggest “handbag” you possibly can. Like this one. (Disclaimer: There will be a lot of Tibi in this story, b/c I am currently very obsessed with Tibi.) When you put this giant handbag on top of your max carryon the carryon will look smaller. Also, you need all the room you can manage. That said, you have no wheels on the handbag, so keep heavier stuff in the carryon.
You will also carry some sort of belt bag. I have this one and I love it. You can also wear the belt solo, wear it with a chain as a crossbody, or wear it as a clutch. But there are plenty of less expensive options. In the belt bag, you’ll have your passport, phone, wallet, ticket, mask, glasses. Stuff you need to get on the plane. And when you get past security, you’ll put this into your giant purse.
Inside the handbag, you’ll have a cosmetic bag that can work as a clutch. That not only holds your cosmetics but gives you another handbag option.
Minimize the cosmetics. IMHO your face will survive not having every single element of a skin routine over 7 days. I just take 2 of these wipes for each day (they clean but also moisturize!) and my SPF, which also acts as a base.
Ok, onto the clothes. First of all, decide on a color palette. That will make it so everything goes with everything. And decide that you’re going to repurpose items and experiment, versus planning looks for each day/event.
Wear the biggest things you’re taking. My suggestion: jeans, blazer, tee, striped sweater around the shoulders, sneakers and socks.
8. Also, wear a belt. I suggest one you can wear at various lengths, like a men’s style belt you have extra holes put in, so you can wear it with jeans or at the waist, looped over and through. A white one would be especially cool.
9. About the sneakers. Don’t take a separate pair to work out. Just deal with it. Pick a pair of cool athletic sneakers from Ssense. Why Ssense? Because SSense curates with a great eye so you’re getting the Nikes (for example) they’ve found because they’re good. Credit to Amy Smilovic for this tip. Pick a pair that’s simple + neutral.
10. Don’t skimp on undies, because you’ll want to take showers at odd times and that means more undies. Take some that are boy shorts you can sleep in.
11. Instead of pajamas, take items you can go down for breakfast in, not just wear to sleep. Think: light leggings and thin tanks, which pack super small. (I love All Access cropped leggings. These work too. You can even make a going out outfit with them.)
12. The big white shirt. This is a workhorse item. You’ll wear it in the evening as a “shacket,” at the pool as a coverup, to breakfast with the tank you slept in, etc.
13. Speaking of the white shirt, please also take a Tide stick and a trial sized bottle of Soak wash in case you need to wash something in the sink.
14. Some sort of slide. Or elevated flip flop. You’ll wear it going to breakfast with the legging and white shirt and belt bag.
15. A slip dress. Wear it to dinner with the blazer over your shoulders. Wear it walking around with the shirt over or tee under, and sneakers. My friend Rose (@thecreativeclassicist) swears by the Tibi slipdress. I like Nili Lotan and this one from Max Mara.
16. 7 tees and tanks. Like 3 white, 3 black, 1 blue. This is my current fave and they fold up tiny. You can wear this over the slip dress so it’s a skirt. Or under it. Also a couple extra tanks to sleep in. They pack so small.
17. Going-out shoes. I like a shoe with a kitten heel, but one with some chunk. (Hello, cobblestones!) Also, bring thin socks that could be cool with the sandal if it’s cold at night. You can wear this with the jeans and the tank and the white shirt. Or get all dressed up with the slip dress and the blazer over your shoulders.
18. A couple interesting pieces of jewelry. Not tons, because you’ll buy some at a street fair. But maybe one major long necklace and one colorful ear cuff.
19. A thin nylon pant. It can be dressed up (like with a black tank and a blazer and clutch) or down (like with a tee and belt bag). It’s super light. It can go to breakfast or a night out. It can be wiped clean.
20. A light, pull on skirt. Add this if you have enough room. It’s easier than shorts for hot days sight seeing. Will go with T shirt, necklace and flip flops. Or white shirt, knotted at the waist. Or tank and sneakers with crossbody.
21. A hat. One that feels like you. It might be a bucket hat. or a baseball hat that’s not a team one. Or a straw Fedora (which you’d have to wear on the plane unless it’s a crushable travel one).
22. If you have a tube top or bra top you like, take that to layer under blazer, over tee, etc. Adds oomph and it’s small.
23. Optional, if room: one wild card. Something thin and light that you’re excited to play around with.
24. And don’t forget. Chargers, sunglasses, hair tie, bathing suit (bonus if it can function as a top too), nude bra, black bra … did I miss anything?