Besides concern about overall training, I'm thinking about my race outfit. There is something mental about having the right shorts or the right shirt with support. I have my fair share of natural padding so like longer shirts and things that aren't too tight (why create more bulge?)
Last year, I found myself shopping for a new shirt the day before the triathlon. This was not a good idea, as I was frustrated with my choices, tired from walking and should have just relaxed the day before the race. Needless to say, I was late getting my bike to check in and wiped out on the way. This year I started a little earlier (a month). My lesson learned is that I should shop year round and get last season's styles on sale in the winter.
Team Estrogen has a great site. A great site in my opinion does not have an overwhelming number of items, but has a solid selection that has been tested out and comes recommended. I bought these De Soto shorts because they are low rise and don't have a really tight band at the bottom. These have been on the bike twice now and are working well. I don't think I'm going to wear these race day because they lack pockets, but have been good on the trainer.
I am still in search of a shirt that is quick dry when I come out of the water, has enough bra support, and is just a bit longer (for vanity reasons). I haven't found it yet, so stay tuned.