What to Pack in Your Carry-On to Survive Stylishly

By the fall of 2012 I was newly married, and my husband and I had 2.5 weeks of vacation time set aside for the honeymoon of our tightly-budgeted dreams. Since honeymoons are intended to be romantic, my newly minted spouse felt we should travel to the 3 most romantic cities in the world: Venice, Barcelona and Paris. What a trip! Romantic cities, yes, but cities that are a flight apart (air travel, nor the prospect of lost luggage is not particularly romantic) and cities with a 25°C temperature range to dress for. My solution for achieving romantic and stylish travel bliss may not seem obvious but it certainly is practical. We packed everything we need for the entire trip into one carry-on suitcase each.

Make It Personal

This is all subjective, of course. The specific colour and style of each piece is what worked for ME. That is to say, these suggestions are simply a jumping off point. Choose items that are your own personal favourites, and bring your own personal style and preferences to the mix. Be sure the entire range of clothes you pack will mix-and-match, and fit all the weather requirements of your trip. Your objective with packing in carry-on-only is to keep your load at a minimum while still dressing stylishly and appropriately for all of your trip. Check out Part 1 of this Packing in a Carry-On series for logistical tips about your specific suitcase and packing methods for getting it all to fit.

How to Begin

The main requirement for getting everything for the entire trip into one carry-on bag is planning. Just like in our post about how to plan your conference wear, planning your outfits for each day and activity is the best way to start the process. To be sure, this is not the most romantic or spontaneous of tasks, but this is how to make it work. Start with a list of all the activities you will be doing on each day of your trip. Include any fancy plans, like celebration dinners, and all events with a specific dress code, such as swimming in the Mediterranean. Use this list to add things onto your personal FINAL packing list and use my basic guidelines about how many of each type of item to bring.

Check the long-term weather forecast for the time you will be at your destination. In a general sense, know what type of temperature and precipitation you are likely to encounter. On our September/October honeymoon, Venice was warm-ish (with flooding and cobblestones) and Barcelona was humid and hot (I’m not used to being so sweaty without moving) while Paris was cold and rainy (with some rainbows thrown in for good measure).

What to Bring: Clothing

Tops

Aim to have all of your tops work underneath your blazer and really think about dressing in layers. The same drapey tank and rolled-up jeans you wear to the beach can work for a rainy 5°C day when you pile on an under-camisole, a wool cardigan, your runners and add your rain jacket. The sweaters saved our freezing butts during October in Paris. My husband took his wool sweater out of his carry-on at the last minute before we left. It was an “I told you so” moment for me, as he ended up buying a beautiful cashmere sweater in Paris (hey, wait a minute…well played, Juan Luis, well played).

Here are the tops you can get by with. Take 4 toppers (2 cardigans, 1 sweater), including that versatile blazer I keep going on about. Add in a lightweight rain jacket that will fold up quite small. Bring 2 short sleeved T-shirts, 2 long sleeved T-shirts and 2 tank top (one camisole, one drapey). Include 2 button up shirts (a denim shirt hides dirt and can go for many wears without washing) and 1 sleeveless dress-up-or-down blouse.

 

Bottoms

All things considered, you need less bottoms than you do tops in order to still have a highly functional capsule wardrobe in your carry-on. Keep the bottoms you bring dark (so you don’t have to do any more than spot clean them) and made out of durable fabric. Jeans fit this criteria but are unfortunately weighty, so limit the denim you have to drag down cobblestone streets.

I recommend 1 pair of jeans, 1 pair of dark ankle- or capri-length pants (classic in an Audrey Hepburn way, yet modern and versatile) and 1 pair of faux leather leggings. Find leggings with a zippered fly and back pockets, more like faux leather skinny jeans, in order to be the most versatile (you can get away without covering your crotch point and butt if your leggings come with a zipper).

On the set of Sabrina, 1954, Mark Shaw/Paramount

Add in a skirt in some uncrushable fabric that you can wear for your fanciest plans. I brought a knife-pleated polyester knee length floppy skirt that I wore to my birthday dinner in Venice. It sounds dreadful when I re-read my description of it, but it really was just right. It worked with all of the shoes, tops and toppers that I brought along, and I even used it over my swim suit at the beach in Barcelona.

Include a durable and versatile day dress in your carry-on. I have this great chambray sack dress with an open neck and short sleeves. I can belt it or not, it works with all of my toppers and I can throw on my runners with it for an easy casual look.

What to Bring: Shoes

Pivotal in packing with just carry-on luggage is the amount of footwear you lug around with you. I know this is a difficult prospect for some of us, but you must limit yourself to only 3 pairs of shoes. Yikes! This was the part of my packing list that I fretted about the most, especially knowing I needed warm weather shoes, and options for cold rain too. Footwear requirements always dictate what outfits I wear.

Bulkiest, With the Most Coverage

First, I brought classic, stylish and comfortable runners. I knew that I was going to be walking more kilometres on vacation than I do in my regular day-to-day working life. Consequently, comfort was a priority. Similarly, my runners needed to be worn with every outfit option I chose. I brought my Converse Chuck Taylor Low Top in black. Pick a comfortable sneaker that you would never wear to the gym. All things considered, your truly-athletic shoes will only make you look like one of THOSE tourists, and ultimately make you a bigger target for thieves. To my classic Chucks, I added a highly supportive athletic shoe insole to increase the comfort level. So glad I did.

Prettiest, With Comfort Required

Second, I needed a versatile and walkable flat that I could wear for fancy when I needed to. I brought along a classic-looking ballet flat that was built with superior cushioning in the foot bed. My Cole Haan flats were made with “Nike Air Technology”. Perfect when we walked about 5K looking for that raved-about Barcelona hole-in-the-wall tapas bar, only to discover it closed 2:30 to 5:30 daily. Oops, my bad. Many brands make well-cushioned slip-on flats. Try Frye, Geox, Born, or Hush Puppies to get started in your search.

Lightest, With Consideration for the Sand

My third and final shoe option had to work in warm weather, at the beach, with my skirt and my jeans and also be comfortable enough for standing in line for hours (!!) at Venice’s Basilica San Marco. My Hush Puppy metallic gladiators fit the bill. The footbed is moulded rubber and the extra strap around the ankle make a gladiator sandal a good bet for extended vacation versatility.

What to Bring: Accessories

• Take cheap but fun sunglasses in a neoprene-type case (the case makes them a little more squish-able).
• Bring a medium sized cross-body bag. Each day I wore my faux leather coral purse, I made sure I put nothing of real value in it. I wore a hidden money belt over one shoulder under my shirt to keep cash and my passport. In my purse I really only kept things that I could stand to lose: a mini city map, a tiny fold-up reusable shopping bag, my oversized scarf, some snacks, lip balm, bandaids and my crushable rain hat. Purses are an easy target for the criminally minded.

• An oversized thin but warm scarf will be useful as a modesty cover in a religious venue, a blanket on the plane, a neck warmer in frigid temperatures, and a sunshade at the beach. Find one in a print or colour that can be worn with ALL of the clothing pieces you bring. I brought my ultra-thin wool leopard print scarf. Leopard is a classic print that can read as a neutral; it coordinates with stripes, plaids, polkadots and florals easily. Just trust me on this one.
• Hunt down a crushable rain hat to use on your trip. It is so much easier to carry around for your entire 3-climate trip than a folding umbrella. Further, it will double as a sunhat for your beach days.
• Bring one basic belt. Obviously, it’s useful for holding up your pants and also for resuscitating  your waist when you’ve piled on all those layers. Find one with a buckle that is not terribly weighty.
• Nothing increases the versatility of your wardrobe like costume jewelry. In my case, I brought 1 statement necklace (a lightweight statement, at that), 1 big pair of earrings, 1 beaded bracelet and a watch.

What to Bring: Undergarments

• Find underpants that are thin and made of a fabric that will dry quickly after washing in your hotel room sink.
• Plan to bring only 2 bras, likely a black one and a nude-to-you one.
• Socks are an important consideration, as they will help you prevent sore feet and blisters if you are doing any amount of walking on your trip. Bring 2 pairs of no-show socks to wear inside your runners. They cover your foot but not your ankle and don’t show above your tie up shoe. Also, mini sock-ettes cover just your toes and heels and they don’t show when you are wearing flats. Ultimately, both types of these mini-socks are easy to wash in the hotel sink and they dry overnight.
• Black tights not only work with the skirt and dress you pack along, they also can be worn under your jeans or faux leather leggings for an extra layer of warmth.
• Pack light pyjamas, either a top and thin pants or a long T-shirt. Even if you don’t wear them to sleep in, pjs are great to change into whenever you get back to your hotel.

 Keep In Mind…

• Pack a tiny packet of travel laundry soap and use it to wash your undergarments during your trip. Hang them overnight on the towel rack or over the shower curtain rod. Most travel equipment supply stores will carry non-liquid soap that is smaller than a pack of tooth floss. Super handy.
• Almost every hotel has a blow-dryer you can use. Don’t waste valuable carry-on space by lugging your hair dryer around with you.
• Don’t bring anything that needs ironing. Period.
• Take some sort of money belt for your peace of mind. Strangely, my husband loved the kind that buckles on to your upper calf. Not my kind of fun.
• Plan to mail home any souvenirs that don’t fit into your carry-on for the trip home.
• Shorts are not as versatile as you might think. In Europe, it may be an old-fashioned rule, but you can look much more like a tourist in your shorts. Besides his swimsuit, my husband didn’t bring any shorts, either. Many churches (often the spot to see the most amazing paintings and architecture) don’t allow shorts, and at the beach you’re better off using that oversized scarf as a cover-up. How does that saying go? When in Rome, do as the Romans do.

My Personal Honeymoon Pack List

Clothes

• Black blazer
• Light belted rain jacket
• Raspberry-coloured drapey cardigan
• Grey thin wool crew-neck cardigan
• Black and grey colour-blocked thin-knit sweater
• Striped T-shirt
• Black drapey T-shirt
• Black long sleeved T-shirt
• Grey long sleeved T-shirt
• Grey drapey tank
• Black camisole for layering
• Pink gingham button up shirt
• Denim button up shirt
• Sleeveless black and white polka dot blouse
• Dark denim skinny jeans
• Black cropped ankle-length pants
• Faux leather leggings
• Pleated skirt
• Denim short sleeved sack dress
• Chuck Taylor Converse
• Black ballet flats
• Metallic gladiators

Accessories

• Sunglasses with crushable case
• Medium cross-body coral purse
• Leopard print oversized scarf
• Rain hat
• Belt to fit jeans and tie around sack dress
• Lightweight statement necklace
• Big fancy earrings
• Delicate necklace with a charm
• Watch
• 6 pairs of quick-dry underwear
• 2 Bras, one black, one nude
• 3 pairs of socks, 2 no-show socks and 1 black cotton/nylon blend (wear them in your hotel room)
• 4 sock-ettes
• Black opaque tights
• Lightweight pyjamas
• Bikini

Toiletries

• Shampoo and Conditioner (in the ziploc for liquids)
• Face wash (ziploc)
• Face cream (ziploc)
• Curl cream for hair (ziplock)
• Mini tooth paste (ziploc)
• Face refresher spray (ziploc)
• Tinted moisturizer (ziploc)
• Face sunscreen (ziploc)
• Mini dry shampoo (ziploc)
• Shave lotion packets (ziploc)
• Rosebud salve (ziploc)
• Razor
• Comb
• Tampons
• Tooth brush
• Mini floss
• Paper nail file
• Nail clippers
• Mini tweezers
• Mini deodorant
• Hair elastics
• Antiseptic wipes
• Prescription meds (in original packs with visible Rx)
• Blister bandaids
• Chewable pepto, tums, tylenol, benadryl, decongestant, melatonin
• Fisherman’s Friend
• Mini eye shadow kit with included brush
• Blush stick (no extra brush needed)
• Eye liner
• Mascara
• Mini lash curler (so handy for carry-on-only travel!)
• Stick concealer

Vital Extras

• Universal adapter (for travel outside North America)
• Mini notebook/pen (keep copies of important phone numbers and itineraries here)
• iPhone/charger/earbuds
• Money belt
• Extra ziploc bags (large + medium)
• Tiny travel pack of non-liquid laundry soap
• Inflatable Travel pillow

To Wear On the Plane:

• Black Blazer
• Grey Drapey Tank
• Black Drapey T-shirt
• Leopard print oversized scarf
• Dark denim skinny jeans
• Belt
• Sock-ettes (having bare feet at airport security is just yuck)
• Ballet flats

So there you have it. I hope sharing my experiences with travelling by carry-on-only will help you with your own future travels. Notably, I revel in the planning part and I am decidedly gleeful on my trip when everything in my luggage works so well.

Dee and I would be happy to help you put together a travel capsule wardrobe from your own closets for you and your family. Furthermore, let us SHOW you how to make it simple. For daily tips, tricks and behind-the-scenes images, follow us on Facebook, Instagram, Twitter and Pinterest.