I would like to thank my friend Adam over at Blue Claw Co. for providing me with the images and a sample bag for testing. – Really great American made travel luggage – go check them out.
A couple months ago I was invited to judge at the Stu Clark Investment Competition at the University of Manitoba.
I'm always humbled to be invited to such events, and putting my best foot forward at all times is important as at events like this you meet potential investors and business partners everywhere.
Even in a hotel lobby when checking in.
As I was standing in line – I had a young professional woman compliment me on my weekender bag. Â She was curious as to where she could find a piece for her father. Â I smiled as moments like this are always a great way to bridge the conversation into a meaningful personal or business connection.
First impressions are important – you've heard me say this many times.
But the non-verbal messages we send go beyond our clothing.
Our choice of luggage and accessories signal to those around us whether we are a frequent traveling executive or a tourist.
Neither of course is better than the other – but the way in which a clerk or your fellow traveler relates to you initially is determined by what they see.
Having said this – I feel it's important that a man own quality traveling tools that make his journey easier and identify him as a professional.  The weekender bag is one such tool – a piece of luggage that should be in every traveling man's arsenal.
What Is A Weekender?
A “weekender” is a gentleman's travel bag designed to hold enough clothing, toiletries, and incidentals for a long weekend trip.
This style of overnight bag is a step up from an ordinary backpack in terms of both carrying capacity and style. It's a roughly rectangular, soft-sided bag that unzips across the top lengthwise, and usually features both a shoulder strap and a briefcase-style handle.
A true weekender should qualify as carry-on luggage for commercial flights. Bigger than that and you're into athletic or duffel bag territory. Roughly speaking you should be looking at a bag that's about 1′ x 1′ x 2′, or in that general neighborhood.
Typical materials are ballistic nylon, canvas, leather, or some combination thereof.
Styles can vary widely, but good ones usually come in either a business style (plain, dark colors with minimal contrast) or a nautical/sporting style (dark cloth with light-colored leather, or vice-versa).
And forget the wheels – if you're packing that heavy you're not really looking for a weekender!
What's Is A Weekender For?
The weekender pretty much says it right in the name: it's meant for overnight or weekend trips where you'll have a couple changes of clothes, your toiletries, and not too much else.
A weekender can fit a sport coat in a pinch, but it's not made for lugging your suits around. They're mostly meant for casual business and personal travel rather than conferences or business meetings. That said, if your line of work doesn't require you to wear a suit, by all means rely on the weekender as your business travel bag too.
Air travel is the primary purpose but not the only one — a weekender makes a fine gym bag or even beach bag as well, and it can fit a whole picnic including a bottle of wine (get the plastic wine glasses, though; you don't want glass shards in the bottom of your good bag).
Why Do You Need A Weekender?
The weekender is your upgrade/replacement for a backpack or an elegant substitute for wheeled travel luggage.
A regular two-strap, school-sized backpack is, let's face it, a kid's tool. It does a great job lugging textbooks and pencil cases around, and when you wear one that's what people are seeing: a school kid. Fine when you're flying back to college or going out on a camping trip, but not great for walking around a city.
Your wheeled travel luggage is perfect for the week trip to your consulting gig in Atlanta – but it's designed to be a practical work-piece for the road warrior.  The weekender leaves the wheels, and does a better job balance an elegant look with functionality.
Switching to a weekender gives you a bit of class. It also gives you a timeless look — men have been carrying the same, soft-sided luggage since the days of cross-continental rail travel.
Even if you don't travel for your job, you want one of these in the back of the closet for unexpected trips. They're the perfect houseguest bag as well as a good business bag. Any trip that's not long enough to warrant a big, checked-luggage style suitcase is one where you'll get good use out of your weekender.
What Makes For A Good Weekender Bag?
Many companies make these bags, under many different names (mini-duffel, travel bag, overnight bag, weekender, etc.). So what makes a good one? Check for a few details that show good construction:
Material – You want a tough bag that won't show wear-and-tear. Waterproofed canvas or nylon makes the best exterior. Leather handles and siding add class and a little extra toughness. Some higher-end models have a waterproof interior as well, making the inside easy to clean.
Build Quality – Pay close attention to the stitching, the thickness of the leather, the steel used on the zipper. Â These are the areas that fail first – make sure they are overbuilt otherwise you'll have problems later down the road.
Color – Dark is more businesslike; light is sportier. Figure out which one you need. Black luggage is pretty much always safe. Navy blue is likewise, and can be a little more eye-catching, especially when paired with light-colored stitching or leather trim.
Size – Always small enough to fit within overhead compartment regulations, but close to as big as you can get within those. You should be able to fit a doubled-over sport coat neatly across the bottom and still have plenty of room for your other gear. A tennis racket also makes a good guide — if you couldn't fit the head of a tennis racket (with the handle sticking out of the zipper) in the main compartment, the bag's a little too small.
Inside Pocket – A classic weekender will not have compartments on the inside – however it should have at least one pocket for important paperwork, jewelry, or other small valuables.
Outside pockets – Not a necessity, but always nice to have, a slit pocket with a zipper on the outside makes a nice place to stuff a book or small electronic device that you can take out during a long flight or while waiting somewhere.
Straps – You want tough straps that are (and it's hard to emphasize this enough) long enough for you. If you're a tall man you may need to buy your own strap for the longer shoulder strap. The bag looses its sporty flair if it's hiked all the way up your shoulder blades when you sling the strap across your chest. Thicker leather or stuffed cloth handles rather than plain webbing straps are nice for the briefcase-style handles, too; they'll be less prone to digging in if you have to hold the bag for a long time.
Ribbing – A sturdy bag will have bands of cloth or leather running around the width of the bag at multiple points. These soft “ribs” give it some structure without making it inflexible. Bags with plastic ribs sewn inside the cloth are cheaper but more prone to breaking, and the ribs can tear through the lining on either side, ruining the bag.
How Much Should A Weekender Cost?
A weekender bag will usually run you anywhere from $100 to over $1000 for a luxury designer piece.
My opinion is to pay for construction over brand name – if it's a well-made bag you could easily end up using it for the rest of your life and passing it on to your children.  My personal recommendation is Blue Claw Co. – made in the USA and owned by my friend Adam who provided me the sample bag for these photos.