Bring your patience! And allow extra time to check in etc. Do you plan to "carry on" your luggage?

Traveling the Tuesday before will be busy but not crazy busy.
I live in a cold climate (Maine) and when I fly somewhere warm I never bring my winter coat with me. Too heavy, too hot, too bulky. It will make me cranky to lug it around, stick it somewhere or wear it. I wear a hat, gloves, sweater and scarf. That will get me from the car to the terminal and back again, the coat and winter boots and thicker gloves(in case the car doesn't start when I return or I couldn't get indoor parking and need to dig out) stay in the car.
For the same heat reasons, but also for the TSA requirements which will have you taking off your shoes, I wouldn't wear hiking boots on the plane: ballet slippers, mules, clogs. I need shoes I can slip out of. For clothing I need layers to shed: my normal attire is long sleeve breathable t-shirt, cashmere sweater, wool scarf/ but really shawl size, it doubles as a blanket, if there is a draft, extra socks in my purse.
The Monday after will be a much busier travel day. Know the procedure for going through security. Even if you have allowed ample time for yourself, the gentleman behind you may not have been such a careful planner, and then he got stuck in traffic. I never want to be the one that makes 'that guy' lose his cool.

I'm assuming your layover in SF is sometime after late morning, but if not and you have a departure out of SF in the morning, a weather delay is likely. Morning flights out of SF are notorious for delays but after noon it's usually good.

Your travel days will not be the craziest days but will still be busy and you can be sure the flights will be full and overbooked by then. Wear the lightest outerwear you can get away with - if you aren't going to need a parka at your destination then leave it home and just layer. Do not wear hiking boots on the plane - you'll regret it. Easy on/off is key for security. Think comfy clothes because you'll be sitting in less than optimal conditions. And my own personal bug-a-boo is do not touch anything in the seat pocket in front of you - that time of year especially, people travel with colds and put their dirty kleenex there so it's a germ minefield. Do everything you can to keep your hands clean because the last thing you want to do is pick up something that gets you sick for your time with family. Enjoy!

As others have said, leave your heavy coat in your car or at home. For speed through TSA checkpoints, go without a belt, heavy jewelry or hair adornments. If you take a scarf, be able to remove it prior to the checkpoint, and wear slip off shoes, not hiking boots or anything with laces or straps that take time to put off and on. Jackets and/or vests have to be removed to go through security, so try to wear as little as possible, or wear easy to remove layers. Security is going to be your toughest obstacle, time-wise, so be sensible about it, and make sure that any lotions, cosmetics, liquids, etc., in your purse or carry-on meet the "no more than 3 ounces" guidelines.

It seems I always forget that last one and end up leaving a brand new or almost new bottle of shampoo, perfume or lotion in the hands of some TSA agent!

Im familar with the TSA, I fly fairly often. Ive not flown during this time of the year. I will need the coat and boots for my destination. I flew to the midwest in January, with only my usual winter gear and nearly froze to death-we dont get snow, just rain, and thats a whole different type of gear! I will pack my boots-I was hoping to gget away with just a carry on, so I guess tthat wont happen.

Forgot about San Fran fog. My plane leaves PDX very early in the am-connector is around 10am. Hope its not too bad that day!

I will be sure to have my phone charged up and headphones at the ready! Since im travelling solo. I dont think itll be as stressful...dont have to deal with grumpy companions. I roll with it pretty well. I chose aisle seats and since i have plenty of time once I get to my destination, im not in a huge hurry to deplane...im sitting near the rear that leg.

Gosh, for the very first time I am taking a trip that has absolutely no agenda! Purely my own pleasure for the majority of the time. This might be the start of something big!

I cannot imagine needing a coat in SoCal at any time of year unless you be at a high elevation like the ski resorts? Of course, I'm one of those people who runs hot; maybe you are one who tends to be cold.

Yes Fun, I'm going to Big Bear for the week. Might spend some time down in the Valley-where I won't need but a light jacket-but helping my sister out at the Christmas tree lot and hikes in the mountains up there-will need my winter gear.

You could send your hiking boots and heavier clothing to your sister ahead of time. Save the packing materials and ask her to drop it back in the USPS or UPS box after you leave.

Have fun!

l.