A weekender is a style of travel bag that is large enough to hold everything you need for one or two nights away from home. They are often more casual and smaller travel than a suitcase and are usually made of leather, canvas or PVC.
1. To trolley sleeve or not
One of the first decisions you need to make about your overnight bag is if you want to be able to bring it with you on longer trips or not. If you want to also be able to bring the same bag as a carry-on during a flight, you will want to make sure it has a trolley sleeve so you can put it on top of your suitcase. Otherwise, carrying both a large weekender bag and a suitcase on wheels separately can be way too much.
You also want to ensure that the bag you pick is small enough to be allowed into the overhead cabin at most airlines. A standard size that is often used is 22x14x9 inches or 56x35x23 cm, but check with the airline you use the most, as it often varies between countries and companies.
2. Are you bringing a spare pair of shoes with you
Most of us cannot go away for a weekend with only the shoes we wear when we leave. Often, you'll need a casual pair of shoes to walk or travel in and another nicer pair to use when you go out for dinners or drinks with friends.
When you need to bring an extra pair of shoes, this can often get bulky. And it can be helpful if your weekender comes with a shoe compartment. It doesn't have to be one specific compartment that can only be used for shoes (it would be pretty tricky to get the size right for that). But it's helpful if there is space where a pair of shoes can be kept upright and stable so they won't mix with everything else you have packed.
3. How many changes of clothes are you bringing
Are you going on a trip where you don't have to change often, or are you bringing a set of gym clothes, one outfit for the museum and two dresses for a friend's birthday dinner?
You should get a decent overview of how much you tend to pack when you go away so you can pick a good size for you. If you have trouble thinking through it, read this article to see everything you need for a weekend away. Cross off the things that you tend to bring and make sure it all fits in the bag you choose.
4. Do you need to get any work done while you're away?
Some people are lucky enough to get a complete break when they go away for a 3-day weekend. But that might not be you.
If you have to check in on work while you're away, it's a good idea to pick a bag with a laptop compartment. Or you could always bring an extra briefcase with you.
The most important thing is to make sure you're not throwing your laptop randomly together with a lot of other stuff. You don't want it to get scratched when you carry the bag around, or worse, get completely crushed or covered in something wet.
You could also need a laptop if you enjoy getting things like writing done while you're away. Or maybe you have a notepad you write down your thoughts in. All of these things require you to have a compartment where you keep your things upright and protected.
5. Are you travelling abroad, and do you need easy access to your wallet or passport?
If you're just loading up your car to drive directly to your destination, you might be fine just throwing everything into one large compartment and unpacking it when you get there. But if you're going by train, stopping on the way, or travelling by plane, you'll usually need a better system than that so you can access important things on your trip there.
It can be very helpful to have a separate interior or exterior pocket that is made in the size of your passport or your cardholder so you can take these directly in and out of the bag when you need them. One thing you really don't want to end up doing is emptying your bag with everyone in the passport control line waiting behind you.
6. How far do you have to carry your bag?
You need to consider both what types of trips you go on and how you're most comfortable carrying your bag.
A classic weekender bag often comes with both detachable crossbody shoulder straps and a pair of sturdy handles that you can grip and carry with your hands. A pair of handles like that can be especially useful when you've picked a heavy load.
7. Do designers and logos matter to you?
Some people can't wait to show off their new designer bag with the leather or canvas covered in logos from the brand that made it. If you work hard for your money, you shouldn't be ashamed of buying something you really like and enjoy.
But if big logos aren't your thing, you can still get a high-quality designer weekender bag. Many brands, including Frost & Forest, only use a small gold-embossed logo at the bottom of the bag, meaning it's not obvious where you have bought it.
You need to decide for yourself and see which style you like. Both colour and design of the bag should combine well with your sense of style, and no one knows what that looks like better than you.