I was thinking about this as part of a discussion thread regarding the upcoming Rehoboth Beach Seashore Marathon and though it would make a useful Blog entry: What to wear?
The general rule of thumb is to dress as though it is 20 degress warmer, but a lot depends a lot on the wind. I'm a huge fan of RaceReady shorts because I can carry my gels and a baggy of Succeed capsules in the nylon pockets (I also carry a small camera, a small packet of lube for chafing, some Ibuprofen, and often my cell phone - I sound like a pack mule!).
I have yet to run in a marathon where I needed pants, but if it's windy or very cold, I have a pair of UnderArmor tights I wear under the shorts and a tight UA shirt I can wear under the tops. I'm a fan of layers - so I often wear a long-sleeve technical shirt under a tank-top or bib shirt. I always carry a big plastic garbage bag with holes cut out for my head and arms, rolled up and rubber-banded. I've never run with it on, but I have worn it after checking my bag to keep warm before the start. I imagine if the weather got nasty during a run, I could put it on. And if I get warm,I don't mind ditching a layer, though that hasn't happened in practice.
So, the answer is, I bring lots of options with me in a bag, and I put off the decision for as long as I can, and then I hope for the best when I check the bag. At the B&A marathon last spring, it was 24 degrees when I was driving to the race and I hemmed and hawed for a long time before deciding what to wear. I ended up in shorts, a long shirt, a short shirt and a vest. If you look at my profile picture here on Active.com (http://community.active.com/people/Steve%20Carton), it was taken during that race and you can see how I dressed that day. You can see the lumps in my pocket where I had ditched my hat and gloves that I wore at the start.
And, never, ever wear anything you haven't worn before.
I don't think it will be that cold on 11/22 for the Rehoboth Marathon, but it might be windy that close to the beach. We'll see as we get closer. But I swear by shorts with pockets, and I love the RaceReady shorts for that reason. I also have a vest with similar pockets sewn into the back. Putting gels and such in regular pockets allows them to bounce around too much for me. I like the webbed pocket style of RaceReady.
There's a cool guide at runners world to assist: http://www.runnersworld.com/cda/whattowear/0,,s6-240-325-330-0-0-0-0-0,00.html