Be sure to weigh your bag before you leave-- you can cram in a lot of extra weight when rolling clothes.
Will move into DHs bag if necessary 
But thanks for the head’s up. It is heavy!!!
Is there a weight limit on carry-on luggage and personal items? All I saw on Alaska’s website was the dimension requirements. A weight limit (50 lbs) was given for checked luggage.
I ended up trying these packing cubes. They are a little darker than the picture but a pretty color and really nice! I started packing the underthings and socks. I love that each cube will hold a separate category of things.
https://www.amazon.com/gp/aw/d/B00HHBR008/ref=sspa_mw_detail_6?ie=UTF8&psc=1&th=1
Also thanks to whoever linked the clear TSA approved quart bags that zip. I ordered two and have mine packed.
Alaska will generally not question the weight of the carryon… only if it looks like you’ve packed a few kettle bells in there and have to drag it on the floor, lol. I have never seen them asking anyone about their carryon weight. Size… it does matter because they are remodeling the overhead bins so old size carryons would create problems.
Never had a US based airline ask about carry on weight. An Asia based airline did on one segment of a trip.
Some Alaska Airlines 737 aircraft have extra large “Space Bins” that fit more typically sized carry on bags (6 instead of 4 per bin). But not all do.
If you’re concerned about weight on checkins, you may want to look into the Scottevest line of clothing. I have a hoodie and jacket from them that I put all my important stuff into. Some foreign airlines (Tiger Air comes to mind) weigh your carryons and the ScotteVest hoodie saved the day because I was able to put a ton of stuff into my jacket.
UCB - check what I wrote. They are supposedly remodeling the planes. New first class seats and bins are coming. The old giant bins will go the way of the dodo bird. That said, when exactly it will happen… no timeframe was given. But the carryon downsizing already happened.
https://www.ktuu.com/content/news/Alaska-Airlines-to-shrink-the-size-of-carry-on-bags-allowed-on-board-in-June-479289063.html says that Alaska changed its carry-on size limit from 24"17"10" to 22"14"9" last June. Considering that the new 22"14"9" limit is in line with what most other airlines had for years, and which carry-on bags and overhead bins were supposedly designed for, it is likely that if the OP has a carry-on bag, it already meets that size (but measure to be sure).
https://blog.alaskaair.com/alaska-airlines/news/to-increase-onboard-storage-alaska-airlines-will-be-first-with-new-space-bins-from-boeing/ describes the Space Bins. They allow more (6 instead of 4) bags per bin (reducing competition for overhead space and reducing gate checking), but they assume 22"14"9" bags. Bigger bags will fit, but then fewer than 6 will fit in each bin.
Yes, I did see the bag size limits and have been confused by what I see in the stores. Most that are advertised as 21” or 22” have external dimensions of 23-24 length plus over on the other dimensions. I don’t currently have a carry on. The last luggage we bought was almost 20 years ago, large, and very heavy. H may take one of those (and have to check it) but I want to pack small and light.
I have done carry on for one week vacation last few trips and it is liberating. We are going to Spain for 9 days this Spring. We have all agreed to do carry on. I think it is doable because the weather will be high 50 to 70.
I think it is tough for people who need hiking shoes and running shoes, they are heavy and bulky. I don’t do much of that, so I can get away with flats.
@psychmomma – sometimes the companies don’t include wheels in their dimensions. Take a tape measure with you when luggage shopping.
What I would pack for San Francisco: 2-3 pairs of leggings, 2 boyfriend cardigans, 1-2 skirts, 1 dress (both need to be wrinkle free when wadded), hiking pants, 4-5 tanks and t shirts, Keen sandals (go anywhere unless someplace fancy which I don’t do). All go into a backpack that can be carried on. I have another bag with food, lightweight laptop, and Kindle. I will take some variation of the above for several overseas trips I have done.
I’m almost all packed and used so much of the great advice above. Thank you all!
I thought I was low maintenance - until I packed my clear quart bag. lol. Lip balm and stick deodorant? I put pretty much anything in there that I thought might be questioned. Do I put meds (pills) in a separate bag that they can look through? Can I take a mirror? If I can’t see my face in 20x magnification I can’t put on makeup.
Do you wear your wedding rings when you travel?
The rest is coming along well. I have a bunch of thin shirts that roll well, a cardigan, and jeans and black pants. I’m still debating the shoes for walking and the boots for evening. I found some short waterproof black blondo booties that might make sense with rain in the forecast for several days.
I have tiny ziplock bags my pharmacist gave me for my Rx that he put a label on for all the Rx my docs want me to have “just in case.” I put the supplements and vitamins in 2 snack-size ziplock bags and write the contents of each bag with sharpie so we know what’s in each bag.
I generally wear my wedding and engagement rings everywhere. When traveling to foreign countries, i sometimes leave my engagement ring at bank safety deposit box, for peace of mind.
I have a weekly pill case and just put my pills for each day in that. It’s never been questioned. I put it in my toiletry kit and never has my kit even been opened. I often bring ambien which I just take on occasion and that’s generally in its original bottle but sometimes I put one or two in a pill case. Again, I travel often and no one’s looking in my toiletry kit.
I do the same as @HImom for the rest: baggies for my supplements/vitamins (but that’s for saving space, not TSA) and also wear my wedding and engagement rings when traveling within the country but sometimes leave my engagement ring in my home safe when traveling internationally. I live in the Bay Area and wear my engagement ring daily
I travel with a fold up magnifying mirror–not a problem.
The only issue I see being flagged during bag screening is liquids that measure greater than 3.4 ounces. Often it’s a water bottle someone forgot about or a too large bottle of sunscreen, lotion, etc. and it shows up when the bag goes through the machine. Oh, and one time, I have no idea why I had a dinnerware knife (not sharp) but it showed up on the screen. They went through my bag looking for the offending item and, once found, I was permitted to keep it.
If you don’t have many pills OR are taking any narcotics, you may wish to keep them in the original pill bottles, but I generally don’t because my docs make me travel with many “just in case” Rx and they take up lots of space when they’re in their bottles.
None of my Rx or vitamins or supplements have been of any interest to TSA.
I always hand carry all Rx and vitamins, supplements and medical equipment, for peace of mind. Having it go astray would be a big issue for me.
You do NOT have to put your stick deodorant in your quart bag. It is a solid. The chapstick is soft, so I’d stick it in there. I believe RX should be labeled with your name on them. I bought a pair of fake rings I wear when I travel and leave the real ones in the safe. I would keep my real ones in I didn’t have the fake ones and just be extra cautious, you can take a mirror. With rain the the forecast, I’d wear the waterproof boots. I’m assuming they are bulky, wear them on the plane.
^^^Above correct, stick deodorant can go in suitcase. I believe that’s a FAQ on the TSA website. I know it has been. Lipstick and lip balm also are suitcase. (Done it myself through many different airports world - wide.).
I travel with many over the counter meds - aspirin, Tylenol, Sudafed, Pepto Bishop, Zicam. Never had any questions any where. Some are in original small bottles, some in manufacturer plastic packaging. The pills themselves are marked. Mirrors are fine.
Security in Hong Kong took my tweezers that had had multiple US TSA passes. I guess they were too pointed. That’s the only “incident “ I’ve ever had with a lot of traveling international and domestic in the last decade.
I’m like the others with engagement ring. It frequently stays at home if my plans include hiking, swimming, adventuring. If it’s a city trip, I’ll wear the full set.
Have a great trip. Watch the people in front of you at security and follow their actions for getting your bag/purse into trays and moving through efficiently. Try not to dilly-dally if you want to avoid fellow travelers rolling their eyes at you. If someone does get upset if you become confused, remember that is their problem, not yours. Some travelers (as well as TSA) aren’t particularly polite. Don’t let it bother you if you encounter it.
My engagement ring is not that valuable - and actually it’s not my original engagement ring which had a tiny diamond that fell out twice. I can’t get my wedding ring off.
One heads up - I had two power sticks for my phone which does not stay charged all day if I take a lot of photos. One of them did not have the voltage marked - it made it through lots of airports including the Hong Kong airport, but got confiscated in mainland China. They let me keep the other one thankfully.