Another carry-on/packing question...Make that 2 questions...

From the US, I doubt anyone will question you. I use that same suitcase and have never measured it but have never had even a second look. Do you intend to check it coming back? Foreign airport personnel seem to be more diligent about size requirements, but YMMV.
The "second item" is supposed to be a personal item like a purse, so your purse will need to go inside the tote. Again, if anyone even bothers to notice. My purse is a small crossbody and I could probably get away with a separate tote if I was wearing that on my person.

Agree with Celeste. It is the low budget airlines that have smaller dimensions/weight and/or not at all. Trick of the trade: anything bought at the airport and placed in an airport bag can be carried on in addition to rules even the low budget airlines. Save a bag from your home airport for the next trip. If they looked it would be hard to explain CDG bag from ATL. My request is please do not come on with 3-4 HEAVY carry ons for two (recent occurrence). It is an example major airlines are not all ways checking. The weight of the bags is a safety issue for those below.

Woofie - I always take a tote in addition to my main bag and use it as a 2nd suitcase to hold my tablet, meds, 3-1-1, shoes if they won't fit into bag, and stuff I might want on the plane. I just drop my little cross body purse down into the tote when boarding.

I travel a lot in North America for work, with one carry on smaller than yours, one small laptop backpack, and my v small cross body purse. All my bags are much less than maximum size and not overfilled. Air Canada never says anything; United usually makes me tuck the cross body in somewhere so I don't have a third item of any size. For Italy last summer, I had the same arrangement except an even smaller daypack (no laptop bag) plus the purse. No one said anything. I confess I was flying business (reward ticket) though.

So despite my personal experiences, I believe you are likely to get some pushback with three items, especially on any budget airlines you might fly and especially in economy. I'd try again to remove a few items (not shoes - my achy feet agree with yours) to leave space for your purse and to squish your carryon down.

Bear in mind your "personal item" can be nearly as large as a carryon suitcase--as long as it can fit under the seat. I usually use a good-sized tote bag for the personal item and either slide my purse inside, or have my purse in my carryon suitcase with just the things I need for the flight in the tote.

Wear your bulkiest shoes and clothes. Maybe put your vitamins in ziploc bags so the bottles don't eat up so much room?

You must have your Rolling Carry-on stuffed like a sausage. The RS specification identifies its size as 20" x 13 ½" x 9" (including wheels), within AA's size requirements. My wife's RS Rolling Carry-on has not had size limit problems.

You can always be a riverboat gambler and hope that the gate personnel will not question the size of your bag. As others note, outbound from the US is less of a risk than returning from Europe. It seems that the gate agents are more vigilant on full flights.

If you are maxed out on your outbound journey when clothing is clean and folds flat or rolls tight, consider the return journey with you bought stuff. American usually allows one free bag on transatlantic/transpacific flights. Carry-on the essentials and check the extra. As long as you can handle the extra bag, you don't lose points checking a bag.

BTW: American's "personal" bag is limited in size to 18 x 14 x 8 inches.

1- May depend on how full the flight is, especially if you are in cattle..errr, coach class, on how strict they are about the extra half inch. If the bag looks like it is 'bulging' you may draw unwanted attention

2- Have not flown AA recently but Alaska is a real stickler for the "2 items" rule. Having 3 items may be a way get you unwanted attention. ( The Alaska announcement quotes the '2 item' limit as a TSA (or FAA?) regulation)

Do you have a travel partner that has a bit of space for some of your 'extras'?

I played around with it a bit. Left out one s/s shirt, used a pocket in my tote for chargers. If I put my 311 bag in my tote, I may make it. But I'm too hot and sweaty right now to test pack again. It's 106* (Phoenix) and I just got thru stripping and bedding my horse's stall. Will try packing again tomorrow. Thank you all for your help and ideas.

Re: "...my purse will fit inside my tote...". By all means do that. Just put the purse in empty. Then fill up the empty space in the purse with whatever.

Keep your carry on bag as it is and add two compression straps on the outside of the bag, cinching it to meet the required thickness. My husband had two cheap belts that we used to cinch one of our soft-sided suitcases to be within legal limits.

I would toss my cross body bag in your tote and if possible, put your extra shoes in that tote as well. The rules are one carry on and one personal item.

We use the same RS Rolling Carry-on. Never any issue on domestic flights. Wasn't an issue on international flights until the time we took an AirFrance A319 from Florence to CDG. The A319 had "normal" size OH bins that the RS Rolling Carry-on fits into just fine even when stuffed, but the gate agent insisted we put our carry-ons into the little metal box with the standard dimensions. Well, wife's bag was quite bloated beyond the 9 inch dimension and did not pass without a lot of squeezing which the agent frowned on. I had to move some stuff from hers into mine on the spot. Our takeaway: you never know when a gate agent will zealously enforce the standards, be prepared with a plan.

1) I haven't flown American in many years, and so I am not sure how picky they are. Usually, if you can fit your bag bottom first into the overhead, you are okay on US carriers. As others have mentioned, foreign airlines and budget airlines tend to be more strict.

Honestly, I would worry about packing a bag that full at the start of a trip. I always seem to accumulate stuff on a trip, and my suitcase/backpack is always more full on the return trip. I would think seriously about packing a small, foldable duffle for the trip home. I use a Sea-To-Summit Ultra Sil Duffle that weighs less than 3 ounces and folds up to a tiny size. It's expensive, but very much worth it to me.

On an overseas flight, you can usually check a bag for free. I know that RS discourages checking luggage, but it's always an option.

2) You can only have one personal item, either a purse or tote or laptop bag. I usually carry a ChicoBag Nomad Tote, into which I stuff an assortment of smaller bags: a camera bag, laptop, small purse, and a small "comfort" bag with items I need for the flight. The ChicoBag always fits under the seat.

My experience lately on AA and Alaska, as well as British Airways, is that the limit for carry on is two pieces. So my very small crossbody bag would go into my "personal item" for boarding. And even after that, often the flight attendants would ask me to remove it from my shoulder for takeoff and place it under the seat.

American has been quite strict on 1 carryon and 1 personal items the last two times I have flown them. Some people were forced to repack/consolidate bags right there at the gate before boarding.
If you are new to "carryon only" I want to give you a word of warning that the airline may, at its discretion, make you gate check your carryon. Always have medicine, papers, valuables in your personal item.

Packing is always a challenge :-). I would definitely get your bags to be compliant - otherwise, there is no point and airlines are getting pickier and pickier which I agree with - if you are going to have a policy, enforce it!
Yes, shoes are definitely bulky and the biggest issue for most of us when packing. So, here are my suggestions:

1.Go over your clothing once again. Are there items that are really more "wants" than "needs". Remember, unless you are going to a very remote destination, you can always buy another shirt if you need it and it makes a great souvenir of your trip! Make sure everything you're taking mixes and matches. 3 pairs of bottoms (shorts, jeans, pants, skirts, etc., etc.) and 4 tops gives you 12 different combinations. Pack less underwear/socks and plan to do sink laundry more often.
2. For OTC meds, I take enough to get me through 2- 3 days unless it's something that I take on a daily basis - which fortunately for me is nothing! But you don't need to take enough meds for stomach issues for every day of your trip - just enough to get you through a weekend until a pharmacy opens. Also, transfer all your toiletries to the smallest containers possible. Depending upon how long you have until you leave, fill a 1 oz. container with shampoo and use that everyday until it runs out - a good guide to measure how much product you really need to bring!
Good luck!!

I am constantly paring down my packing list. I travel for long periods, so I just don't feel like I can underpack items that I know I will use regularly. But this trip, I am having some luggage issues (broken zipper on bag extension), and have convinced myself that I can bring less and remain clothed, groomed, medicated and happy.

My bag weighs 9 kilo on EasyJet's scale. I can probably get it down to 8. The daybag with meds is another story...but it also holds my small messenger bag on the plane.

Wear your heaviest shoes and clothes on the plane if it makes a difference in space or weight.

If you do take a chance and pack it past 9 ", I suggest wearing it on your back at boarding instead of wheeling it. On my flight from Newark to Cleveland the gate agent was forcing those with wheeled bags smaller than my Osprey 46L backpack to gate check (the situation where they take your bag but give it back to you at the destination gate not baggage claim). I assumed I would need to do the same but she looked at the bag on my back and said "go ahead honey, you're fine". It took me 5 minutes to cram that pack into the very small overhead bin. : )

So you've gone through and pared down wants into needs, have managed to fit everything into a small bag, and you feel like you're good to go. If you're only flying on the transatlantic legs of the trip with a legacy carrier and using other transportation once you're there (ie. you're paying for a checked bag whether you use the service or not), put anything valuable or absolutely necessary in the tote plus underwear, socks, and a t-shirt, and then check the big bag.

The point of carry on-only is to think about what you really need and to eliminate time in baggage claim. You've done the thinking, and international immigration lines tend to rather neutralize any baggage wait. And airports are actually often more pleasant when you aren't feeling like a turtle hauling your entire home with you as you go to and from gates.

Besides, if you buy more than a pair of earrings and a fridge magnet on the trip, you'll end up filling the tote and checking a bag anyways on the way home anyways.

If they flag your bag, you can follow Sarah Murdoch's strategy: step out of line, go put more clothes on from your bag, and get back into boarding line. :-)

There is an art to packing the RS Rolling carryon - be sure you're filling out the corners so the bag expands like it should. I have to pack my old RS 21" and my newer RS 20" Rolling carryon bags with completely different strategies.

If you're really worried, you could make a preemptive trip to an airport and see if your bag will squish into the American sizer. I'm guessing it will.

Woofie - If you're only doing a carry-on, I don't think you'll be able to take the Pepto. Take the chewables with you in a zip lock.
On the trips where I only took a carryon and a personal item (even to Ireland for 10 days!) I found if I took along a large tote bag (I used a thirtyone bag) I could fit everything I'd need in both. I put my toiletries, electronics, wallet, my RS book, snacks, and a change of clothes in the tote, just on the off chance that my carryon bag had to be checked b/c the flight and overheads were full. If worse came to worse, I had something clean to change in to. I also brought along a cheap folding nylon bag that if necessary could be packed and brought on board as a carryon, checking my rolling carryon. I packed my empty purse in the carryon. With AA, depending on when you board, you may not get any overhead room at all and be forced to let them stuff it in their glove box, where they put strollers, guitars, wedding dresses, etc...

Happy traveling!

I used Eagle Creek compression cubes like the ones Sarah Murdock suggested on my recent month-long trip to Italy. They did a great job of compressing, but the disadvantage is that only the air comes out, not the weight of the clothes, making it easier to overpack.

My total wardrobe included 3 pairs of pants, 4 layering/sleeping pieces (2 tanks, 2 short-sleeved -- really needed only 1 each), 6 tops (really needed only 4), 3 bras (could've done with only 2), 3 shapewear tanks (could've taken only 2), 8 pairs of panties (not going to cut back there), 3 pairs of compression socks (2 would've been enough), 3 pairs ankle socks (2 would've been okay), 1 rain jacket (used only once, but a must).

I took 2 pairs of shoes, one for wet situations. I think I should've left the wet ones home and taken a pair of sandals or flats. I also should have taken a pair of shorts for sitting around the room. While there I bought a smushable hat for the sun, a "house" dress for sitting around the room because I didn't take shorts, and a long linen top at a market for fun.

All that soft stuff (except the rain jacket) and some non-clothing items fit in 2 large and 2 small compression cubes like these. I "pack" the dirty clothes in a compression cube until I can wash them. I have other cubes, but none are as good as these. I can't praise them enough.

Everything fit in this bag without extending it. I measured it at home fully packed except for what I was wearing in transit, and it met all the size requirements. Nobody questioned it going any direction on any Delta plane, including the smallest one between Atlanta and Tucson. It fit fine in the overhead bin, wheels or handle out.

I have a variety of totes. The one I used on my last trip was big enough to hold my meds for a month, phone, mini-tablet, money belt (while on the plane) and very small crossbody bag. I like the totes that you can slide securely over a u-shaped handle.

There are all kinds ways to pack light successfully. As limited as my list looks and as small as the duffle and tote look, there were at least 2 women on my RS Village Italy tour this summer who had even smaller bags. They are my packing inspirations for the next trip, even though it will be much cooler than mid-June to mid-July in Italy.

Assume that you will be limited to the stated two items. What I do is empty my purse and shove it into one of my carryons. I have that same carryon bag, and it's wonderful! But I also carry a backpack as my other item. The carryon goes in the bin above my seat, wheels first, of course, and the backpack goes underneath the seat in front of me.

Anything I might need on the flight, goes into the backpack so that I don't have to fuss with getting up and finding things in the carryon bag above my head. As a previous poster said, there is always a chance that your wheeled bag may be gate checked. If that happens, make sure anything important - passport, cash, credit cards, electronics, meds without which you will be seriously hampered, itinerary - are shoved into whatever bag is going beneath the seat in front of you.

Depending on your final destination, OTC supplements may be available there, freeing up room in your bag. Flip flops are usually available in other places as well. I don't know if that would help, but it would free up a little space in your bags.

Hope you have a fabulous trip!!!

Thanks everyone for your ideas, experience and help. A couple test packs and a few changes made everything work within the required space. I moved a few things to the tote and still have room in the tote for my purse and knitting. (Knitting fingerless gloves using alpaca yarn on bamboo needles, small and lightweight project for flying time and to relax at night. The nylon knitting bag can double as a light weight tote/backpack if needed.)
I rearranged the packing cubes, eliminated the dress which saved a pound. Added a small compression bag for sleeping shorts and tank top to keep things neater. Cut back on a couple supplements and otc meds, taking pills instead of liquids and taking fewer bug repellant wipes. All that brought the carry-on down to 9(ish) inches deep.
Except for buying a camera, I'm ready to go. That's next week's project.
Kathy, 34 days and counting down.

Another reason to go carry-on only is to avoid the pain of lost luggage. Back in 2000 I lost a suitcase on a flight out of Prague. I never knew what came of it. It contained two bottle of Czech wine, a decent blazer, a decent coat, a Czech crystal vase, about a week's worth of clothes, and of course the suitcase itself. All told, it was probably a bit more than $1000 of stuff. However, if you lose something on an international flight, they pay by the pound, not by actual value. So, I got maybe 30-40 cents on the dollar for my loss. Ever since, I go carry-on only and have never regretted it. I often wonder why I packed so much crap in the past. You also get the advantage of being far more mobile, which is always a good thing when traveling.