This post covers the spectrum of bags: from selecting your primary suitcase and personal item to exploring backpacks for various travel needs and the smaller organizational accessories vital for a smooth trip.

Choosing Your Main Travel Bag

To Wheel or Not to Wheel

More often than not, the first decision you have to make is whether you want to carry your bag or wheel it. That means deciding between the categories of a duffle bag, messenger or backpack, or a suitcase or duffle on wheels. There are a few questions I’d recommend asking yourself to help you decide:

First, are you physically capable of carrying a lot? If you have injuries or are vulnerable in some way, don’t risk it if you don’t have to. You’ll be much more comfortable with a wheeled suitcase.

But if it is an option for you, my next question is:

How much do you need to bring?

If you’re going for a weekend, by all means, choose the backpack or duffle! They’re small and easy to pack. They fit on trains, in car trunks, buses, and airplanes big and small. Plus, if that’s the only bag you’re bringing, most discount airlines will count that as your one free bag.

Will you be on public transportation a lot during your travels?

Backpacks are a great option if you’re backpacking. If your trip involves jumping from city to city, staying in hostels, doing a more outdoorsy trip, or a combo of both, you’ll want to be nimble. Not having a suitcase is especially practical when you’re taking a lot of public transportation.

Is there a chance you’ll need to check your bag?

If at some point in your trip, you buy a bottle of hot sauce or pick up something that can’t be taken on the plane, is your travel bag suitable to be checked? Or will your stuff get broken? You can always buy a small cheap suitcase for the return flight home. So don’t worry too much. But that is something to consider if you’re likely to have non-carry-on-friendly items in your bag.

Non-Wheeled Travel Bags

If you’re leaning toward a non-wheeled option and wondering what to get, let’s discuss some options.

Garment Bags for Air Travel

For business trips or trips where you’re packing a suit or a dress, travel garment bags are a popular choice. If you’re flying first or business class, there’s usually a closet for the staff to hang your bag, or even occasionally in Economy if you ask nicely.

These are convenient bags, but keep in mind you still have to carry them on one shoulder, which could get heavy. And, they don’t fit quite so well in overhead cabins.

The Garment Bag from Away

Duffle Bags

The next category is duffle bags, and there are some cool ones on the market right now, so take your time digging into the details. Some even have built-in straps so they can be converted into a backpack. These are some of my favourite models, although I’m more of a wheeled suitcase gal myself, so when I say I’m a fan, I mostly mean I think they’re cool.

Calpak Duffle Bag


That brings me to actual backpacks. Backpacks come in various styles, each with its features and benefits. Extensive research and recommendations tailored to your trip type can help in choosing the ideal backpack.

This is also a category I don’t know that well since I don’t backpack on my trips. But I’d recommend reading reviews, checking features, looking at weight, and size recommendations for your height, and even going on Reddit to get recommendations for people taking similar trips to yours.

From the models I’ve seen, there are a few general categories of backpacks: the briefcase style that fully unzips open, the ones that are filled from the top, but with secret side zippers to access your content, and the more modular ones.

Tortuga backpacks

Wheeled Suitcases for Travel

Choosing Between Checked or Carry-On Size

The decision between a checked or carry-on suitcase depends on your trip length and the items you plan to pack. Be mindful of airline size limits to avoid unexpected issues.

The first question is size: checked or carry-on. This is up to you. I travelled for one month in a carry-on, just like I checked a bag for a one-week trip because of the things I was packing. It’s all based on your trip length, what you’re bringing, or planning to bring back. Just remember to be prepared to pay for a checked bag and to always check the size limits for carry-ons to avoid any surprises.

As a quick guide, regional jets or discount airlines will allow only the smallest suitcases while bigger companies and bigger planes can accommodate larger carry-ons. Also, the higher your class or airline status, the earlier you board and the more chance of getting primo overhead bin space.

Roam luggage

Hardshell, Softshell or Duffle Suitcase

Regardless of the size of your suitcase, I recommend getting four-wheel suitcases over two-wheel and getting one with high-quality zippers and a sturdy telescopic handle.

Whether you’re team soft shell or hardshell, both have pros and cons! I have a whole blog post on how to decide between a softshell suitcase or a hardshell one.

There are also other variants like the business suitcase, which I don’t see that often in the wild but is good for quick overnighters. There are also duffle bags with wheels which can offer some of the portability of a duffle with the convenience of wheels if you get tired.

Selecting Your Personal Item for The Plane

Picking the Right Bag for Your Trip

Next up, let’s talk about another super important bag to consider if you’re flying: your personal item. Choosing between a large purse, travel tote, backpack, or small duffle depends on accessibility during the flight and usefulness throughout the trip. Practicality and ease of access are critical factors.

For me, the first criterion for all of them was that they fit my laptop. After that, it mostly depended on what bag would be easiest to access in flight. And, third, which one would serve me the most on my trip? When I picked a small backpack, it was because I knew I’d be commuting around on my trip and wanted to be hands-free.

The Away Everywhere Bag is one of my fave travel personal items!

For the duffle, I had a few overnight trips planned into my longer trip and needed something for those quick getaways. And for a large purse, often it was the option I knew I would use most for everyday carry during my trip and just made sense with the outfits I’d planned.

For a personal item, my favourites are the ones that have a zipper close top. But for short plane rides, I’ve been sacrificing some of those cool features like zippers, pockets, and a luggage handle sleeve and choosing more fashionable bags. That’s because I need a bag that I will use during the trip and want something stylish. But one hack during travel is using the Cincha travel belt to secure pretty much any bag to my suitcase.

Can You Sneak on Another Small Bag?

Now, there’s a sneakily third category of bag you may want to consider for travel days and that’s the extra personal item. It’s the small purse or sling you wear close to your body which can hold phone, wallet, a passport and won’t count as a personal item. You can also usually get away with an extra tote bag that you fill with magazines and snacks at the airport. Sometimes I’ll shove that into my personal item just as I’m scanning my ticket and boarding and then take it out when I am getting settled in my seat. Or, the opposite. I’ll put my little third item into a shopping bag from the airport so it just looks like airport snacks.

Sling bag by Troubadour

Travel Purses, Day Backpacks, and Totes

Let’s talk about the bags you’re packing in your suitcase. I mean the purses, totes, and backpacks you’ll wear at your destination. For these, my best advice is to pack the flattest ones possible that expand the most. My favourites are the Baggu or Everlane collapsible variety or the leather ones that pack flat when not in use. Do I always follow my advice? Of course not. But if I’m tight on space, my ultimate travel purse is my medium Le Pliage purse which is flat, easy to clean, and so versatile. I can always fit it in no matter how full my suitcase is.

Bags for Every Activity

When I pick which bags to pack, I follow the same general criteria as the rest of my packing list: weather, activities, and vibe. Is this a business trip where I’ll need my laptop most of the time? Then a large, polished tote works well. Is this a more outdoorsy trip? Then a backpack is great. If it’s rainy, I would avoid suede bags and go for nylon and if it’s there’s a fancy occasion, then I’d pack some sort of clutch.

If I plan to go sightseeing and take a lot of photos or videos, then I need something large enough for my camera and a water bottle. But if I want to be hands-free, crossbody or little backpacks are a great option. Depending on the season, there are some bags I would or wouldn’t pack. In summer, I like straw bags, beaded bags, cotton bags and generally more summery bags. While in winter, I lean more toward the nylon and leather ones. Another big difference is the strap length. When I’m wearing a winter coat, I need a generous shoulder strap length or an adjustable crossbody to get over all the layers.

Do I Need an Anti-Theft Bag?

I want to take a second to talk about bags and anti-theft. This is a whole category of bags and accessories that are always marketed towards travellers. People often wonder: do I really need this? It’s a hard question to answer because the people I know who have had their things stolen, the whole bag was swiped from under a table at a restaurant, or they were robbed at knifepoint. So, it’s hard to say if an anti-theft bag really would have helped. But if you’re visiting a crowded, touristy area, know you’ll likely look out of place, and want to be sure, here’s a rundown of your options.


First, there are moneybelts and wallets, meant to be concealed. If all you carry is money, cards, and passports, this is better than leaving them in an easy-to-access unzipped pocket. My personal favourite stylish alternative to this is the fanny pack worn across the chest. It’s on my person, it’s close to me, and I would notice if anyone got close enough to cut the strap or yank at my bag.

Slash-resistant crossbody bags

Some crossbody bags offer slash-resistant straps. You can buy purses like this or just swap out the strap on a purse you like with one of these straps. Chain link straps are by default slash-resistant but are not the most comfortable option for long periods.

The other feature of these purses is the zipper and this is something I would recommend looking into. Zippers that clip shut are much harder to open for thieves. But you don’t have to buy a bag with this feature built-in. You can purchase little clips on Amazon that will add this extra layer of protection to most bags.

Anti-theft backpacks

Anti-theft backpacks are where I think these features are most valuable. With purses and cross-body bags, you are keeping your stuff close to you. But with a backpack, anybody could be opening the zippers and you’d never notice. So I recommend adding these zipper clips or getting a backpack with anti-theft features built in.

Can I Bring my Designer Purse on Vacation?

There’s a lot to be said for blending in when travelling. If you’re a bit rough and tumble with your travel gear, it also might not be the place to bring an expensive bag. If you’re going to Paris or Milan, I think it’s safer to bring your Chanel or Fendi bag than other places. But still be aware that big logos will attract attention.

My preference, if I’m bringing a more expensive bag, is to take the ones that are more “if you know you know”, or more low-key options. Or, if you are going to an event but travelling through a sketchy part of town, put your purse in a grocery tote and then take it out, fold up the tote bag and put it in your purse.

Shopping Totes

On the topic of tote bags, I always pack a shopping tote with me, because you never know. I use these for plane snacks and magazines at the gate, picking up groceries for my Airbnb and even sitting on it when a bench is wet after a rainshower. Bonus points if you pick up a super local tote bag. I’m talking about the fruit and veggie vendor down the street that you can keep as a souvenir. That’s a great way to blend in and look like a local.

Pouches, Organizers, and Wallets for Travel

Now, I’m going to list off a bunch of little bags and organizers that are by no means necessary, but worth considering to make your packing and travel a little more organized.


I have a couple of different wallets I use, in tandem. Kind of like a Russian doll set of wallets if you will. I recently for the Apple Wallet and love it for credit card, ID, and bus pass. But I also carry more cards in a small card wallet and then place that in my larger zip wallet, which also fits a passport, receipts, and a key. It can fit my phone too. If I’m just going out for dinner, I’ll something shove everything in here and forgo a purse. Just don’t lose it by leaving it on a table or countertop in a store.

Dopp kits

I prefer dopp kits that have transparent compartments which are friendly and just easy to see into so I can quickly grab the things I need. You can also just use a Ziploc bag if you don’t want to spend money on a fancy dopp kit.

Tech bags

I also have two sizes of tech carriers: just the essentials and the whole kit. If you’re a content creator, I highly recommend getting a padded carrier for your tech accessories.

Tech organizer by Bellroy

Garment bag insert

For special occasions, I’ll pack my formalwear in a garment bag that clips into my suitcase.

Shoe bags and packing cubes

For shoes, I bring bags or packing cubes to keep them separate from my clean clothes. I am also a fan of packing cubes to stay organized and fit more in my suitcase with the added compression, but it’s not obligatory to achieve an organized suitcase.

Packing cubes by Away

Dirty laundry bag

I always bring a zipped laundry bag to keep things separated on the go.


On summer trips, I also bring a drybag where I can put my bathing suit if I go for a dip right before packing up my suitcase, or if I’m going straight to dinner from the beach or pool.

Various pouches

I keep things for my flight in a pouch too, like earplugs, bandaids, medicine, hand sanitizer, sanitizer wipes, a few masks, gum, and hair ties. It’s just my emergency kit that I always keep handy.

Final tips

This might seem like a lot of bags, but trust me, it’s one of the elements of packing I recommend tackling with thoughtfulness and research. It makes such a difference when you can count on your bag to carry you and your stuff through a trip without issues. Over time, you’ll find the right mix for your travel style but I hope these tips will help guide you through some of the options and considerations.