My Secret To Living Out Of A Carry-On

Filed Under: Advice, Travel

When I first moved into hotels my luggage situation was a mess… as summed up in the picture below.


Over time I’ve realized that if you’re going to live out of suitcases full time you need to be super-minimalist and just live out of a carry-on. While it means my wardrobe is quite limited, it also saves me dozens of hours a year of waiting at baggage claim, not to mention the potential headache of lost bags (though amazingly enough even carry-ons can get lost).

Up until this year I had a Tumi 20″ Alpha International, as well as the Tumi Alpha laptop bag. It was a sleek set, if not a bit corporate looking. On US airlines you’re entitled to take aboard one carry-on and one “personal item,” so the 20″ rollaboard was my carry-on, and the laptop bag was my personal item.

But then I discovered the wonders of the weekender bag (mine is from Killspencer) . Yes, most people travel with a weekender bag as their carry-on. I, on the other hand, travel with my weekender bag as my personal item. And it has probably increased my carry-on capacity by about 50%.


Is it within the spirit of carry-on policies? Perhaps not. But let’s look at the actual rules. Here’s American’s carry-on baggage policy:

Carry-on bag

Your carry-on bag should be:

Personal item

Your personal item must be smaller than your carry-on, able to fit under the seat in front of you and can include:

My weekender bag is smaller than my carry-on, and it can fit (very snugly) underneath the seat in front of me… so it does technically qualify!

Some will likely claim I’m being selfish by carrying on a weekender bag as a personal item, but the reality is that I always put it underneath the seat in front of me, so it’s not inconveniencing anyone.

To be honest I’m still kind of shocked I haven’t been called out on it a single time. Not even a single comment from a gate agent. Because it is rather huge. The only mention I’ve received of it is from a flight attendant on a non-US carrier who literally laughed when she saw the size of my weekender bag, and said “well done… wow.”

But it’s awesome. Not only does it hold everything my laptop bag previously held (laptop, electronics, toiletries, etc.), but it also holds several pairs of shoes, undershirts, etc.

Does anyone else us my strategy of using a weekender bag as a personal item in order to maximize the amount you can carry-on?

  1. My biggest problem with traveling with a weekender-type bag is that a lot of the stuff that can be organized neatly in all of the dedicated pockets of a backpack/briefcase/messenger bag, like passport, loyalty cards, cords, pens, umbrella, etc. just ends up somewhere at the bottom of a weekender bag and is often hard to find. Have you come up with a solution to that problem?

  2. I have a pretty large Vera Bradley tote that I haul around. I don’t think it’s as large as yours. I can fit two to three days worth of clothes in it. I always take it, but its super handy when the airline charges checked bag fees. On Southwest, I usually use it as my carry-on.

  3. Maybe I’m missing the point here, but why would you want to lug all that luggage around? So much easier to just check it in and collect at the other end.

  4. I don’t use a weekend per-se, but I do switch to a decent sized backpack instead of a laptop bag when I am going to be away for longer periods of time. So it’s the same idea.

  5. So your laptop and cords, camera, passport, etc. are all in your weekender bag floating around?

    I need a new briefcase/messenger bag but leaning towards something with more pockets/compartments as I can’t stand my current clutter situation. However what I am finding is that pockets = weight.

  6. I never do this for work but yes for 1 to 2 week long vacations with lots of outfit changes (formal, beachwear etc.) I’ll do a roller board and a weekender bag. Sometimes I push it with that definition as a few duffels I use approach the limits of a regular carryon…BUT they generally fit under the seat unless there’s plenty of overhead space as there tends to be on international flights.

    My solution for floating objects is little stand alone pouch organizers – Tumi sells some as do other companies. So I have a dopp kit for toiletries, a tumi pouch for cords and electronic stuff, and then my Everlane weekender has one side interior zip pocket that can accommodate small items, pens, passport, etc. and it’s sewn to the top of the bag so always accessible / doesn’t sink to the bottom.

  7. I think more and more people are doing this, especially if they have to pay to check a bag. I do this but with a duffle bag instead of a weekender, and one that’s smaller than my carry-on. Personally, I don’t see an issue with this as most weekender/duffle bags will fit under the seat in front. If the flight isn’t full, you can probably find space in the overhead bins for the weekender as well.

    @Bgriff As far as organization goes – I find ziploc bags or cheap travel cases hold things quite well. With the amount of premium class traveling Lucky does, he can probably re-purpose amenity kits as organizers. A Rimowa case full of chargers and cords, anybody?

  8. Have you looked at a backpack-style bag instead, like a Tortuga? Arguably not as fashionable but I’m a big fan of shifting that weight from my hands to my back.

  9. It also saves you from hiring a stylist… and also saves you from minutes of deciding what to wear each morning! 😉 You remind me some of the GLEE characters who always wore a uniform every day (i.e. cheerleaders, football folks, Warblers, etc.)

  10. @Bgriff – Some bags offer more organization than others. I have a Tumi Sport Duffel that has pockets on three sides that keep the small stuff organized. I’ve found, like Lucky, that a duffel/weekender substantially increases capacity, and I’ve also never had a problem with a gate agent (though more often than not I’m flying up front). The duffel also takes up a lot less space in the overhead – roughly 10 in. of width versus 14 or so for most carry-ons.

  11. Last week I had a problem where BA couldn’t see the proper luggage allowance on an AA issued ticket, so I couldn’t check two bags for free as I had been intending. I just took a huge duffel bag (not very full, but it still looked big when carrying it) as my carry on. Nobody said anything.

    I’ve done the similar with large duffel bags before never had anybody say anything. I think they are stealth bags where the sizing rules don’t apply.

  12. Killspencer is a great brand. I live a few blocks from their Sunset Blvd shop. I have their camo jacquard dopp kitt/folio. A bit overpriced, but definitely a piece not everybody has access to.

  13. For a petite woman (4’11) like me, that never works as people ALWAYS think my bags are oversized. I can’t even stand next to a 22 inch carryon without getting a second look from agents, assuming my bag is oversized. I’ve resorted to a small hiking backpack that doesn’t look too big but can fit a few days worth of clothes.

  14. you might want to add a few asterisks: * i don’t know what the back of the plane looks like ** don’t try this in the back of the plane and/or if not Ex Plat ** don’t try this if you’re in anything but boarding group 1 **** none of this works on LCC’s- particularly in SE Asia. and, finally ***** i am in the .0001% of airline travelers, a well known travel blogger, featured on TV and major publications, and i can get away with most anything with nary a word…. and you can’t. so, unless you’re Gary Leff, this post wasn’t for you.

  15. Took the same setup on a trip to Europe this year (Tumi international carry-on and a Bric’s weekender type duffel). No issues with AA or BA for intra-Europe flights, which tend to be stingier with baggage allowance. I would imagine you won’t have issues with the weekender because you tend to fly in F, and it fits within those bag sizer contraptions, but people in economy are likely to get some grief from gate agents.

  16. ..And I meant to add, I flew Business and First. So totally agree with the others, this would be a different conversation if you’re flying Economy. Even on a recent domestic F flight on AA, the gate agent asked for volunteers to check in their bags for free (the oversold/overcrowded drill). I went up to volunteer my bag, she looked at my F ticket and said, “Oh, we never restrict the F pax, we’re looking for Economy pax to check their bags.”

  17. @abby and others – I fly in economy all the time and am not even top tier status and have never had issues with this. I’m only Premier Gold and have never had an agent question me with a duffel as my second carry on (especially since it looks smaller than the roller board).

    As long as it fits under the seat in front of you an agent shouldn’t have a problem with it period regardless of where you are on the plane. They really only care about overhead space and you’re entitled to place one bag up there and one under your seat. Not everything Ben does can be attributed to “only first class” or “only top tier elite”…

  18. Tumi Alpha is SO awful. Tumi Generation FXT Ballistic is where it is at, surely? Very disappointed in you, Ben.

  19. Uh yea, my mom brings one slightly bigger and has never had any bother. Abby- where has Benjamin been on TV? Link?

  20. I highly recommend duffels. Filson, J Fold, Herschel; all make durable bags with ample pocket space. Never had an issue carrying these on and I fly CRJs too damn often.

  21. Abbey, that’s way overstated. Funny, but still overstated. The second bag doesn’t even go up top, after all. Good enough, though, to take today’s Best Post of the Day prize.

    The real secret here is simply to travel with a soft, no-wheels bag, which is what I do. You’ll never have to gate check even on RJs. Guaranteed. Plus Pavel agrees with me.

    And, Mr. Lego, Ben does a great job on TV. Keeps it simple.

  22. That is exactly what I take for most of my travel. I use a Longchamp bag very similar in size to your weekender. Once I began using a larger second bag, it made all the difference.

  23. You have some good luck.
    I would not suggest trying that on United.
    I’ve been yelled at more times then I care to count. To the point now, I just yell back. 1K , business class.
    The last time I got threaten with the sizer. It fit, of course, but even I know when my weekender is full it’s pushing it.

  24. @Lucky, I’m assuming that you use these bags for ALL of your travel. I’m curious to know how you’ve gotten away with it in Europe. AFAIK, many intra-Europe flights restrict you to ONE bag in Economy, with no allowance for a “personal item.”

  25. Your weekend bag is $475 USD (from the website)? wow…………

    Would a gym bag not do the trick? or a “smaller” gym bag?

  26. These are all great comments. I would add a couple of thoughts. About small items that seem to get lost or scattered to the bottom of bag, I always travel with ziplock bags of several sizes. A gallon bag is a good container for incidentals and is easy to find inside a carry-on. I have had no problems switching entirely to carry-on instead of checking bags except on European/International carriers that have weight as well as a size limitations. On a flight to Switzerland a year ago on SWISS, the carry-on weight restrictions were so low, if it were not for a friendly clerk at the check-in counter, I would have had to travel with an almost empty rollaway bag.

  27. I use canvas LL Bean Boat n’ Tote zippered tote bags as my “weekender” bags; I’ve hauled them all over the world. They fit beautifully under the seat in front of me (they squash really well), and manage to hold my purse, laptop, toiletries and a wide variety of other things. I can also use them as grocery/shopping bags at my destination. I never go anywhere without one.

  28. As a commercial photographer who needs to get pricey equipment on flights regularly, I am very aware of AA’s baggage policies. The personal item can be 36″ or less. First carry-on is up to 45″. Your weekender bag is 41.5″. Kudos to you for getting it onboard. Worst case they make you gate check it, right! For me gate checking fifty thousands of dollars in cameras and lenses is NIOT an option, so I try and stick to the rules, especially after having a few “incidents” with gate agents policing the rules rather strictly.

  29. You travel with several pairs of shoes Lucky? That, and your carry on bulk, suggest to me that you really haven’t scratched the surface of efficient and effective carry on travel.

    Realistically you can cut shoes right back to two at the maximum – sports shoes (covers gym and casual/rambling) and dressy but still versatile shoes (for everything else, I find a pair of R M Williams airport friendly boots quite good for this ‘catch all’ shoe).

    Carry on can be pinged for size AND weight, so you have to critically cull the bulky and heavy and search for lightweight and versatile options.

    While I can understand the attraction of roller bags, they are terribly weighty and in all honesty are unnecessary if you can pack wisely (because even a long trip can be done healthy and happy with not much more than an over the shoulder bag). Every millimetre of space and gram of weight counts.

  30. You’ve mentioned before that your roller bag is 20 inches. The max size for US carriers is 22 iches. Why not have a roller bag with maximum dimensions?

    In addition a weekender must be carried or placed ontop of your roller bag which makes it top heavy. Personally I have a 22 inches Travelpro Crew 9 roller bag and tote. I place the tote on a hood which balances my rollerbag so it’s very easy to carry.

    For the record I fly a lot. 2016 included 6 Australia trips, 2 Asia, 2 Europe, 1 South America and a few US trips. I’m living out of a bag way more than I’m home.

  31. Wow, that’s a real load Lucky.

    My standard for luggage is one item that will allow me to run for a train while being chased by gypsy’s that found out you won big at a Russian casino.

    I use mountaineering gear, but now that I added a SLR digital camera to my travel items, I may have to re-think my current setup.


  32. I’ve found my biggest problem with weekender bags has to do with the weight distribution. I’ll have the front pockets loaded with heavy electronics/papers that I need quick access to which will generally overbalance the suitcase it’s sitting on.

    Ben I’m curious how you go about keeping nicer clothes (button-downs, blazers, etc.) wrinkle free while traveling with only carry-on luggage? I’ve tried EC packing folders and cubes only to find they like to leave pretty pronounced wrinkles.

  33. I use a High Sierra rolling backpack pack with zip on day pack. The daypack detaches from main pack for checkin and is my personal item and the rolling backpack with extendable handle and wheels and hidden backpack shoulder straps is my carryon. Zipped together they transport in the airport and on public transportation as 1 complete unit with wheels and handle

  34. I actually use the largest Longchamps “Les Pliages” bag, similar size as yours and even though the Pliage bags don’t come with straps, i managed to convince the sales girl in the Longchamp Shop @ Suvarnabhumi Airport to give me a strap fm another bag that matched. But i hardly use the strap, i store it on my wheely and roll it around.

  35. i travel with a Costco Ricardo polycarb spinner wheel carry on (does anyone have any recs for something smaller that’ll fit in Air Canada’s tiny sizers? must still have spinner wheels) and a backpack for everything else. I can’t really do totes because I’m admittedly weaksauce and have trouble carrying a large heavy tote. Wheels are my friend, or carrying it on my back (hence the backpack).

  36. In there day Filofax made a back pack that was perfect for documents/files and clothes. Bought three still on my second. The straps are designed to lock onto a carry on, with tablets and not files these days hardly weighs a thing.

  37. @ Jerry:
    $475 may seem to be a lot for a piece of luggage used for only a couple of trips per year, but in my experience somewhat bigger investments in really good equipment normally support themselves pretty fast when it comes to the things you (have to) use on a daily basis. For Lucky, his luggage items basically serve as some kind of household stuff like pieces of furniture do for other people.

  38. Decent luggage is worth it’s money, it lasts long and is satisfying to use, and very, very personal…. I’ve used a Samsonite hardshell as checked luggage for years, won’t part with it, it’s been through a lot and seems almost indestructible. For carryon I switch between Porsche, Samsonite and Moleskine, depending on occasion. Hardly anything which is more personal, kind of funny, everyone I know vigorously sticks to his or her choice.

  39. I bought my boyfriend a Tumi Alpha Deluxe Carry-On Satchel and it’s fantastic. It opens up like a doctor’s bag, has tons of pockets, and fits within most carriers’ requirements of a personal item. I think it’s no longer being made but you can still find them (including NWT) on eBay.

  40. @ Max — Hah, truth be told I don’t do it very well. It does tend to get wrinkled, though I do my best to fold it as neatly as possible.

  41. @ James — Because many international airlines take issue with the Tumi 22″. While it’s marketed as being 22″, in practice it’s more like 23″, so I’ve had friends who have the bag and often have to gate check it. I’d rather overload my 20″ and not have to deal with that.

  42. @ Kieran — I travel with three pairs of shoes. I need running shoes, “formal” shoes I can wear with a suit, and something inbetween. I don’t think that’s unreasonable.

  43. @ Jerry — I don’t have many material possessions, so I at least like to have “quality” products for the few things I do have.

  44. @ Abdel Rahim Abdallah — On US airlines it does sometimes become an issue, given how economy is always overcrowded, so then they put economy bags into first class bins.

  45. @ AdamH — I have a sleeve for the laptop itself, and then use amenity kits to organize all my cords, so they’re not just floating around in the bag.

  46. @ Sean M. — Because in the US baggage claim tends to be pretty inefficient, so it would probably add about 30 minutes to the end of every flight I took. When flying an average of three times a week, that translates to a LOT of time waiting.

  47. @ Bgriff — I do have lots of “things” to keep stuff organized, like a laptop sleeve, amenity kits for cords, toiletries, etc. I find that helps. The bag also has a pocket on each side.

  48. I’ve been in the air an average of one hour a day since the mid 90’s. For the past few years, my “personal item” has been a heavily stuffed TSA-laptop-friendly Tom Bihn “Brain Bag” Backpack ( and my clothes and toiletries have been in an over-the-shoulder-slung Tom Bihn “Aeronaut 45” (

    Luckily, I can board in the first group, and I try to get the bulkhead seat so that both bags are required to be in the overhead. The Brain Bag can sometimes be squished under the seat in front of me, but I find many coach seats have things hanging down from them keeping me from using that space for that bag. I’ve also never been challenged based on size, but once or twice based on weight, since they’re both about 20 pounds each.

    I’m so happy to have discovered wheel-less travel. Wheels take up 20% of the space and 10% of the weight limits. They also use up one hand while running through airports, and don’t help with stairs or cobblestone roads. And they make you “double-wide” unless you awkwardly roll the bag directly behind you. Once I lost those wheels, my airport transits have been a breeze.

  49. I used to do something like this. I had a small backpack that would count as a second carry-on. So I’d put it inside a shopping bag. DING! Now it’s a personal item.

  50. @Star, AC actually has pretty average carry on allowance, you can bring one carry on bag, a “personal item” and a purse. I’d recommend going to The Bay when they have one of their luggage sales and taking a tape-measure with you. Also, soft-sided personal items are a good way to cheat the system since the way to check compatibility is to stick them in the sizer so duffle bags can be squished into one while hard bags can’t.

    I actually use a London Fog spinerette a my carry on and a London Fog small cabin bag as my personal item since it can double as my travel purse. I can fit a good two weeks or more worth of clothes in there thanks to packing cubes.

  51. I travel the world with a check in bag of exactly 23kg (50lbs) and a laptop backpack. Everything i own is basically inside it. I do not understand how you can reduce everything you own into just a carry on. What do you have inside?

  52. I live out of two bags, and I like to use clear punches with different colored trim to keep things organized. The different colors allow me to grab exactly what I need on the first try and the transparent pouches mean I can see exactly where inside my desired item is. Saves time, which adds up.

    My clothing packing cubes aren’t clear, but they are also different colors, again letting me grab the right one first try. I color code them to what I feel are the most appropriate seasonal colors. For instance, my summer clothes are in a white cube and winter clothes in a dark burgundy. Spring in a green cube and fall clothes in an orange one.

    I also need 3 pairs of shoes: boots, sandals and flats. Everything fits neatly in an 18″ spinner, and I use a Samsonite Small Underseater as my personal item. However, I’m seriously considering using that under seat bag as my carry on and a smaller backpack as my personal item, for ultra travel light mobility. I am a small “woman of a certain age”, and I want to be able to stay in places that don’t have elevators without worrying about getting my luggage up the stairs.

  53. Your old baggage situation is my current one, albeit split between my girlfriend and me.
    Nevertheless, we could definitely do with downsizing to carry-on size sooner rather than later!
    I’m surprised you haven’t been asked to check that weekender bag though as it looks like it may struggle to fit inside the little steel frames at the check-in desk!

  54. biggest problem with your luggage is the WEIGHT. that 20 inch carry on luggage itself weighs so many pounds when EMPTY (i am betting around 7-8 pounds which is very heavy). i have seen super thin n light backpacks (like “the minimalist”) that are far better. weight is a real problem, as of course is girth. i use a packable daypack along with a cvr-617 targus backpack as my carry on which is about 1.5 pounds empty and can squish down quite well. it is also rugged and costs about $40 to $50 on average. i also do laundry often to mitigate having to bring more clothing. i wear socks that are ankle cut to save space and weight on normal size socks. i have other tricks i do to cut WEIGHT. it is not the amount of stuff but the weight that is the real problem.

  55. You can buy the biggest carry on possible for BA and EasyJet.
    It really is huge, and bigger then much have as their check in.

  56. If I ever need to check a bag I know I am overpacked. My tip is that I have discovered a wonderful secret – everywhere you travel there are laundries. Not the hotel laundry which is hideously expensive, but the local laundry often around the corner to the hotel (search Google for “nearest laundry to X”.

    Whether I am traveling on a three day or a thirty-day trip, my formula is the same: 5 shirts; 5 sets underwear and 5 socks; 3 ties,1 spare pair pants, and my wash and medical kits. Add to that my travel clothes which I wear on the flight – a sports jacket (good for meetings and evenings) and pants, walking shoes (good for meeting and walking the city) and a thin merino wool sweater for winter travel and cool evenings.

    I never check baggage and travel with my two-wheel roll-aboard and a back-pack for my work stuff. Only once got refused and that was in Johannesburg where South African weighed all carry-on baggage at the gate with a 7kg total limit for both bags.

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