How to Pack for 1 Month of Travel in Carry-on Luggage
Packing,  Travel Tips

How to Pack for 1 Month of Travel in Carry-on Luggage

As an avid and experienced traveler, I often move around during my trip, changing hotels frequently. I also love to travel to unique locations, sometimes difficult to reach, or just off the beaten path. Lastly, one of my favorite components of travel is the ability to be spontaneous and just go with the flow. In order to travel on my own terms, I cannot be bogged down with cumbersome luggage, so I almost always travel with only carry-on bags. People often ask me how to pack for 1 month of travel in carry-on luggage. So, here are my tips.

Also see 5 Quick Tips to Organize Your Packing

Assess Your Plans

  • How many days are you traveling?
  • What is the weather like?
  • Consider the types of activities you are planning.
  • Will you need a coat?
  • Where is your destination?
Photo by Brett Zeck 

How Many Days are You Traveling

My general rule is to pack outfits for 1 week per each month of travel. Then, mix and match to create new outfits from them. For example, if you bring a pair of cute black stretch pants, you could pair them with a tee and sneakers for the day, and then put a blouse and sandals on for evening, utilizing the same pants.

Remember that by mixing and matching you can likely create at least 2 weeks worth of outfits out of 1 week’s clothing. Also, many items can be reworn such as jeans and blouses. If need be, freshen your clothes by hand washing them in the sink. Alternately, most towns have a laundromat and some even have laundry service where they will offer a “fluff and fold” service while you are out exploring.

Laundry Day in Rapallo, Italy

What is the Weather Like?

Pack practically for the weather in your destination. If you know it will be chilly, do not pack sundresses or items that you will likely never use. If you suddenly have an unexpected warm day, you can usually do a little shopping at your destination.

Layers are usually a great option. They cover a range of temperatures. Also, many clothes that can layer are thinner and do not take up so much space in your luggage. Consider these comfortable and versatile long sleeved tees. You can dress them down with jeans or jogging shorts. You can also add accessories like this scarf and dress them up. Pair a long sleeved tee with a black skirt to go anywhere.

How to Pack for 1 Month of Travel in Carry-on Luggage
Check Out This Cool Scarf Available Now!

Sweaters are bulky and can take up a great deal of room in luggage. Consider packing thinner sweaters that you can layer. Also, since sweaters take a long time to dry if washed, bring quick drying tee shirts to wear underneath to keep your sweaters clean and prevent the need for frequent washing.

In warmer climates, I try to stay lightweight, maybe 1 pair of jeans and an open front sweater like these fashionable duster cardigans, or this lightweight jacket for breezy nights, that will match everything. Other than that, breezy sundresses that wash and dry easily and quickly. Of course, a dress can be dressed up or down and go day to night easily.

Consider the Types of Activities You are Planning: How to Pack for 1 Month of Travel in Carry-on Luggage

The types of activities I am planning definitely play a role in my packing. If I know I am mostly traveling in warm sunny islands, I am sure to have a bathing suit, a cover up, yoga pants, flip flops, flowing dresses, and beach wear. However if I am hiking, I pack long pants, shorts, tees, hiking boots, and socks. I especially love these hiking pants that can double as shorts and are nice enough to wear out at night too. For city trips, I choose sensible shoes and fashionable casuals. Then, I enhance them with accessories such as a scarf or earrings.

Many destinations offer a combination of activities which can be a bit trickier in terms of packing. Here I pack versatile pieces that again can be layered and dressed up or down. These items may include black stretch pants, a black skirt, a dress, jeans, a few blouses, a few tee shirts, and a scarf. These few garments can take me hiking, zip lining, to the beach, a night club, dinner, and more.

How to Pack for 1 Month of Travel in Carry-on Luggage

Will you need a coat?

Most of the time I travel, I have some sort of coat with me. Depending on the climate, I decide whether it should be a more substantial winter jacket or something lightweight.

If I do need a winter jacket, I invested in this type of jacket that is thin, but has the technology to be very warm, especially with layers underneath. I love this coat because I can essentially control how warm it is based on what I wear under it. Best of all, it literally folds down into a tiny pouch and takes almost zero room in my luggage.

Otherwise, I tend to like a windbreaker that doubles as a rain jacket in a somewhat waterproof material. Also thin, this jacket can look fashionable enough in the right color and is really versatile. A jean jacket tends to look cute, but takes up space and does not do great in wet conditions. So, again, consider your destination and its’ weather.

Where is Your Destination?

In many destinations, casual, laid back fashion is completely acceptable. However, if you are headed to Milan, Paris, or another iconic fashion destination, perhaps you want to step it up. Totally understandable. Most likely, you can still accomplish this in a carry-on bag.

You can definitely pack more pieces if you choose breezier, lightweight fabrics. Pack slacks that can pair with 2 or 3 amazing blouses. Wear a blazer under your coat on the plane. Pack several dresses and use accessories or the blazer to freshen them. Tights can make dresses and skirts warmer. Pair skirts with multiple tops to create new looks.

Create a Packing List: How to Pack for 1 Month of Travel in Carry-on Luggage

When I create my packing list, I divide it into essentially 6 sections. This helps me determine how to pack for 1 Month of Travel in Carry-on Luggage.

  1. Toiletries and Essentials
  2. Electronics and Other
  3. Medical
  4. Clothing
  5. Accessories
  6. Important Documents

*Download Your Free Jenny In Wanderland Travel Packing Checklist Now

How to Pack for 1 Month of Travel in Carry-on Luggage
Photo by Gabrielle Henderson

How to Pack for 1 Month of Travel in Carry-on Luggage

The 6 categories of “What to pack” are laid out for you on the Jenny In Wanderland Travel Packing List. There is space to checkoff items as you pack. However, some of my packing categories may need some clarification, which you will find below. Also, what works for me may not be exactly what works for you, so feel free to substitute.

Click to share the top 3 items that you always pack, no matter what, when you travel.

1. Toiletries and Essentials

On the Jenny in Wanderland packing checklist, you will find a solid list of essentials to pack. My list always includes my own shampoo and conditioner. I find that many free products provided at hotels just don’t condition my long hair enough to get the knots out, especially after swimming. I also like to have my usual makeup, my electric toothbrush, my preferred hair brush, and toothpaste. If you forget something, most items are available throughout the world, but may be more costly or not the brand you are used to using.

2. Electronics and Other

These days electronics seem to be essential, no matter how much you want to get away from it all. A smartphone is important not only to communicate, but to check in to hotels, show your vaccine card, read menus, and use maps.

Additional equipment I travel with includes my camera with various lenses, a laptop to keep you updated on Jenny In Wanderland, and E-reader. I really love my e-reader because I bought a version that only allows you to read. It still has all the great features such as the ability to read easily in the sun, but this way, I can set aside my reading time and not get distracted by social media or email.

How to Pack for 1 Month of Travel in Carry-on Luggage

3. Medical

It is definitely important to pack any medication that you must take regularly. Although many medications are available throughout the world, they can have different names, or be difficult to get. Additionally, your prescription may not always be valid in a foreign country. So, if you can, bring what you need with you. Also, always keep your medication with you when traveling. In case you get separated from your luggage, or you have a delay, you will always have what you need.

4. Clothing – How to Pack for 1 Month of Travel in Carry-on Luggage

In addition to determining your length of travel the climate, and your planned activities, there is the more basic question of “What exactly do I put in my bag?

In general, I follow what is on the Jenny packing checklist; making substitutions depending on the specifics of my trip.

In cooler weather, I tend to have the following clothes:

  • 1 pair of jeans
  • dressier pants such as floral printed or colored jeans or slacks
  • black leggings
  • 1 pair hiking/sweat pants
  • 3 dresses
  • 1 pair of black tights
  • 3 tee shirts
  • 1-2 camisole style tank tops
  • 2 long sleeved tees
  • 4-5 blouses
  • cardigan duster sweater
  • bathing suit
  • 1 coat
  • 3-4 cute sweaters/sweatshirts

In warmer climates:

  • 1 pair of jeans
  • black skirt plus 1 other
  • 1 pair white pants
  • 1 pair convertible hiking pants
  • 5 tee shirts
  • 2 camisole style tank tops
  • 2 long sleeved tees
  • 5-6 blouses
  • lightweight sweater or jacket
  • bathing suit
  • Cover up
  • 6 dresses
How to Pack for 1 Month of Travel in Carry-on Luggage

Other Tips

A few items that I always have in my luggage are 2-4 solid color tees and both a black and white tank top. Not only can you pair these items with any bottom for warm daytimes, but they can also be worn under sweaters during cooler travel. Wearing a tee or tank under your sweaters helps to protect them from sweat so that they do not need to be washed often. Therefore, you can just wash the tee or tank, which dries much more quickly.

Additionally, by adding a patterned scarf or long beaded necklace, you can dress these tops up or down. You can wear these tops for a hike, with pants, or even a skirt and sandals. I absolutely love these tees because the material helps keeps your body temperature comfortable, they control sweat, take up almost no space, and dry super quickly. They never show wear and are fitted. I literally have dozens of them!

A long sleeved button shirt down can double as a swimsuit coverup and a cute top for day or night. I love this wrinkle free one that can be tucked in or out. Blouses cover your shoulders in local sites where this is a requirement and can also help protect you from the sun. If it is breezy, you can throw a blouse on over most anything to warm up. Best of all, blouses are generally thin, easy to pack, and can tie around your waist or roll into your purse to have with you whenever you need it.

Muted solid colors such as blacks, tans, whites, and blues are easy to mix and match. Adding a few stripes or floral prints by means of blouses can add a fashionable edge.

How to Pack for 1 Month of Travel in Carry-on Luggage

Let’s Talk Shoes – How to Pack for 1 Month of Travel in Carry-on Luggage

I generally pack 3-5 pairs of shoes, depending on how I answered the above questions (destination, weather, activities, etc.).


I always have a pair of sneakers because I like to walk a great deal, be it to tour, photograph, or exercise. Also, even if I am not planning to hike, sneakers can be used for most hiking if the opportunity arises. Occasionally you will need closed-toed shoes for activities such as zip lining and horse back riding. With sneakers I am always prepared. Many women pair jogging shoes with dresses and skirts these days and it is considered sensible fashion.

Hiking Boots

If I know for sure I will be hiking or that the ground will be very wet or muddy, I often bring hiking boots. Since these are large and take up space in luggage, I always tie them to the outside of my carry-on bag. While having them dangle can be a bit annoying at times, it is like having a freebie pair of shoes since they are on the exterior! Alternately, you could choose to pack your sneakers this way instead. In addition to sneakers, which I always have, I have a summer or winter shoe packing routine.

Additional Winter Shoes

In winter, cold, or wet destinations, I usually fly in comfortable black boots. Upon arrival, these are my go to shoe to dress up leggings and jeans, as well as to have a walkable heel with dresses. In addition, I pack 1 pair of cute flats. They may be like this, or even these, that can be worn with most anything.

Additional Summer Shoes

In summer or warmer weather, I forego the boots. I usually pack flip flops, a pair of sandals in a neutral color that look nice with everything, and a pair of chunky heels for evening that are easy to walk in. Silver or gold tone sandals tend to add a little extra pizazz. I bring sneakers and usually hiking boots too.

How to Pack for 1 Month of Travel in Carry-on Luggage

5. Accessories

A few carefully selected accessories will not only pull all of your fashion together, but can also serve as additional wardrobe. For example, the scarf that I wore around my neck to dress up my tees, doubled as a bathing suit cover up when I unexpectedly found myself in Monaco.

Scarves, casual cardigans, and jewelry can all dress up a casual outfit and add a fashionable flair. Additionally, many accessories can keep you warm on a cool night or protect you from the sun, as well.

6. Important Documents

Keep your travel documents, such as your passport and drivers license, with you at all times while traveling, unless locked in a secure place. You never know when you might be separated from your luggage. You should never put important documents in checked luggage. I like to place my passport in a plastic ziplock bag, inside my carry-on. Just in case something in my bag leaks, plastic will protect it. Same goes for other important documents.

Steps for How to Pack for 1 Month of Travel in Carry-on Luggage

  1. Create a Checklist: List everything you think of that you need to bring. Check it off as you pack it to help avoid forgetting things. I also use my list at the end to go through and see if there is anything in my bag I feel I can do without. If so, I lighten my load.
  2. Layout The Items You Want to Pack: Place all the items on a bed or table, spread out so that you can see them. This makes it easier to evaluate the size and type of luggage you will need, to visualize outfits, and notice if anything is missing.
  3. Choose Your Luggage: Choose the size and shape carry-on that best suits your needs. Take into consideration how often you are moving around (wheeled bags may be helpful), if you need to stow your bag (like on a cruise; a duffle is foldable), and if you can benefit from wheels (some situations are more conducive to a back pack).
  4. Get Organized: I love to use packing cubes and ZipLock bags. Once you pack often enough, you will find yourself packing the same way repeatedly. For example, I always know that in the small front compartment of my backpack, I will find my pen, Tylenol, and a hairband. I place any toiletry that has any chance of spilling in a sealed Ziplock, and most everything else is sorted into packing cubes.
  5. Pack your Bags: Be sure to check each item off your list as you place it in your luggage.
How to Pack for 1 Month of Travel in Carry-on Luggage

Choosing your Carry-on Luggage

Selecting carry-on luggage mostly comes down to personal choice, although there are definitely some considerations. For the purposes of packing carry-on for your entire trip, I feel an upright wheeled bag is one of the best options.

Since you will presumably be putting a good a good amount of items in the bag, it may be a bit heavy. Having wheels that you can pull will make it easier. Other options may be a backpack or duffle bag. For me, in order to go completely carry-on for a long trip, I need 2 bags. This is the limit of what most airlines worldwide permit. You usually can have one piece of luggage and one personal item.

I almost always choose my upright wheeled bag combined with a day size back pack. My back pack usually contains my electronics, documents, medications, toiletries, and shoes. The wheeled bag holds my clothing and accessories. Depending on how well I pack, sometimes there is space in the roller bag for a pair of shoes or something out of my backpack to lighten its load.

Please see Jenny In Wanderland article on How to Choose Your Carry-on Luggage for a detailed look at which bag to choose and why.

Utilizing Packing Cubes

I do not know what I did before I used packing cubes. Seriously! I love them because they enable me to keep my luggage in order for my entire trip, even if I’m in a new hotel every night. The learning curve for the traveler is to organize the cubes at the beginning in a way that is natural for you. Think of each cube as a drawer. I simulate my dresser and closet at home. This way, you always know where to look for your items.

How to Pack for 1 Month of Travel in Carry-on Luggage

How to Use Packing Cubes

The only real trick is that every time that you finish with something, put it back in its correct spot. Then, you will never have to repack each time you move and you will always know where everything is. To repack, just put the cubes back in your suitcase and zip it.

In a standard upright wheeled carry-on, I can usually fit 4 medium size packing cubes, 2 on each side stacked flat, one on top of the other. Additionally, I usually put a smaller one wedged on its side between the 4 pouches in the middle to hold my underwear and socks.

I use one cube for bottoms; Skirts, pants, shorts and jeans. The second contains all of my tops. Number three is for my dresses, and the fourth holds sweaters, sweatshirts, bathing suit, and accessories.

Which Packing Cubes to Buy

I like the netted packing cubes that allow your clothes to breathe, like these. Also, some sets come with varying sized cubes which makes them difficult to stack. I prefer 4 of the same size and just 1 or 2 of the smaller ones. It is an investment, but I’ve had mine for years and I doubt I’d need to replace them anytime soon.

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