Timbuk2 Wingman Suitcase

I bought this item to use as my only bag when traveling light. I like to fly discount carriers, some of which charge even for carry on bags. I usually would just use a backpack with a laptop compartment and put it under the seat in front me. The main problem with that strategy was that clothes would not stay folded and end up wrinkled. When I saw this bag, I knew it was exactly what I was looking for.

I ordered both the small and medium to inspect them in person and compare the sizes. I came to the following conclusion:

Medium: May fit under the seat if it is not fully loaded, but when fully loaded will likely only fit in the overhead bin.

Small: Will easily fit under the seat, even when full loaded.

I decided to go with the small based on this observation and returned the medium. The small will fit a decent amount of folded clothes in the main compartment and I can even squeeze a pair of shoes in there (men's size 11), but this reduces the amount of space available in the side pockets. The laptop compartment is fairly large, even on the small, and I'm able to fit a 14" Dell Latitude with extended battery (13.9" x 10.3" x 1.3") easily.

I can only really find two cons, which aren't a big deal to me, but may be for others:

As other reviews have mentioned, the laptop compartment is hard to zip if the cinch straps inside the main compartment are pulled tight. This problem is worse when there are very few clothes, since the strap will be cinched tighter. When I have it loaded with a large amount of clothes, it's not really a problem.

There is no water bottle holder. One could easily fit on the side opposite the main zippers (and I'm considering adding one), so I don't see why it wasn't included.

Overall, this a very quality bag and will last a very long time. I was able to purchase it on sale and I'm not sure I'd be willing to pay full price, but if you can find it discounted I think it's worth it.

I took this on a 3-week trip to Italy and carried it on airplanes, boats, and trains, as my only luggage. It held up really well and fit all of my stuff (although I did laundry during the trip), including shoes and souveniers. I mostly carried it backpack-style. If you want to travel light, this backpack is very lightweight and pretty roomy. I definitely recommend it.

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I fly twice a week for work, and frequently find myself stuck on the smaller regional jets that some airlines have fallen in love with. The overhead bins on many of these planes will not accommodate even a smaller "rollaboard" suitcase. My Eagle Creek rollaboard JUST MISSES fitting into a CRJ900 overhead by 3/4" because of its lower rigid frame, so I'm forced to gate-check it. The Timbuk2 Wingman (Medium) has the same length-by-width footprint as my rollaboard (21" by 14"), and fits into the small overhead bins! No need to gate-check my bag and wait 10-15 minutes in the jetway for the bag to be unloaded and brought up!

I was also very pleased to find that if you use the Eagle Creek Pack-It Cubes (which I do) to organize your packing, the Wingman nicely fits a pair of the full sized Cubes as a layer. So, it can easily hold 4 full Pack It Cubes (2 per layer) or 2 Cubes and the larger Eagle Creek Folder (I have the 18" folder but the 20" should fit as well) with some room to spare.

For me, the backpack straps complete the package. I had to stand in customs lines on my first trip with this bag, and never experienced any fatigue, where I'm sure I would have wanted to set the bag down if I'd used the included shoulder strap.

The computer pocket is huge, but I have to admit I won't put my Macbook Pro 13" in there without the additional protection of a sleeve. I'm using the Timbuk2 Quickie. It fits in the pocket, and I just pull it out before tossing the Wingman bag into the overhead.

Time and travel will tell how durable this bag is. My wife has owned some other Timbuk2 bags that she carries 20 pounds of books and paperwork in. With a lifetime guarantee, I'm certainly willing to see how well this bag stands up to life on tho road.

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This is a very lightweight, portable option to a wheel aboard carry on. I wish it was an inch or two thicker to be closer to the max carry on size but it serves my purposes well. The first time I used this was on a 12 day trip to Europe where we were taking trains from city to city and I didn't want to be dragging my luggage on the subway. This was my only bag in addition to a small shoulder bag. I fit 6 days worth of clothes in here plus my toiletries and a few miscellaneous items.

The bottom pocket is great for a spare pair of shoes or dirty laundry since it has a flexible divider. The top pocket is great for your 3-1-1 liquids bag for quick access going through security. The small front pocket is great for stashing boarding passes or a thin guide book or a stocking cap and gloves. The back pocket which is designed for a laptop is also great for all your important paperwork for your trip since if you wear this as a backpack that side is inaccessible to pickpockets. The mesh pocket in the flap when you open the main compartment is good for small items like socks and underwear. The straps in the main compartment help keep everything from sliding around when cinched tight.

I have only carried this as a backpack and my one suggestion is to add a sternum strap for comfort which you can buy on Amazon or elsewhere from the manufacturer. Using a packing folder organizer in it helps add structure but isn't necessary. I removed the shoulder strap for carrying it as a messenger bag and use that on a different bag. I have used this on a half dozen trips and its great for anywhere from a weekend to a week if you're a light packer. I even fit it under the seat on a smaller plane that didn't have dividers between the underseat area in front of my husband and I. The small size would probably be better for that purpose but I don't really need two of these.

For trips where a roller bag is inconvenient or too big, this is my go to bag now.

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This bag was great for a trip with the kids. As a Dad I'm always carrying something besides my stuff. Being able to use this as a backpack while still having the organizational features of luggage was great. I always had 2 hands available and the bag didn't flop around like a messenger bag would have. This is not a real backpack however. If your thinking about hiking the appalachian trail with this thing you'll be sorry. Its comfortable enough to get you through the airport but its not a super long distance hauler. To be fair I don't think it could be. Most real backpacks of this size have some sort of frame and weigh twice as much which would not be an advantage on a plane. I normally travel very light. I don't bring more than 4 days of clothing as I always find a way to clean them. Having said that this bag swallowed this easily. I didn't bring a suit or a change of shoes which would have filled more of this bag. The suit also would have needed some protection or at least the dry cleaning bag as it might wrinkle. I found the internal straps very helpful in keeping the clothes compact and less lumpy. I also got the packing cube which is helpful. The bag fit very easily on all the planes and the messenger strap did double duty replacing a cheap strap on a soft sided cooler during the trip. All and all if you travel light and need both hands to manage other stuff and want to get through airports quickly this bag is perfect. If I still traveled a lot for business I might use this bag. I always found the wheeled bags would fall over or be difficult to get around in a crowd. It was nice not to be trailing a rolling bag. I just don't know if it would wrinkle your suit.