I'm actually from Florida which is part of the reason my wardrobe is so inappropriate for most other parts of the country.
As I understand it, the weather is 40-65 Fahrenheit most of the year. I got three pairs of Cole Haan shoes for work (two loafers plus the boots) on sale and combined that with an Amex offer, averaging ~$70 a shoe after the discount and including tax.
I visited my friend in SF last December and we actually just got rained on for a week (and it wasn't warm rain like we get in FL). I got the boots I did because I'd like to be prepared if that happens on a work day. I also got a big beefy wooden handle umbrella from Macy's as well as a smaller, foldable emergency umbrella from the Eddie Bauer outlet that I can carry in my messenger bag.
I have a *very* light Nautica windbreaker than I use for the warm Florida rain, but I don't think that holds up well in 45 degree weather so I got a Michael Kors wool peacoat from Macy's on sale for about $90. I also got a Strellson jacket which is a bit heavier than my Nautica one but still functions as a raincoat for about $110 (vs $340 ish retail).
I have a Macy's Amex store card that's gotten me good offers on lots of stuff from the Macy's website, when combined with the sales they have, usually results in good savings (I don't think I've ever spent more than $100 for an item there). I got three Ralph sportcoats for $50-80 a pop.
I really like the quality of Brooks Brothers sport shirts and was able to take advantage of some offers they run to get 8 of them for about $340.
The temps in SF range from 50-70°F throughout the year. You can probably take most of your Florida clothes, add a fleece or lightweight down jacket (Uniqlo has nice ones) and a waterproof shell and it will get you through the year in SF. What I'm saying is you don't need to buy weather-specific gear.
My suggestion would have been to hold off on buying a lot of new clothes until you get to SF, then do your shopping there. (As someone who has done cross-country moves, I learned that the less I had to schlep myself the better). Unless you are an unconventional size, you can totally buy your wool or cotton trousers at any JCrew/Banana Republic/Gap store. And I highly recommend Brooks Brothers non-iron button-down shirts -- it'll save you a mint on dry cleaning. But as you've shopped already, you seem to have selected pretty well, except snow boots -- what's that for?
Here are temp and precip ranges over the past couple of years. As you can see it's mild throughout the year. Even when the lows dip to the 40's, it rarely stays there as it warms up to the 50's during the day. Rains are generally reserved in the winter and spring (unless it's an El Nino year). The best time of the year, weather-wise, is usually September to mid-November. "Summer" can be chilly with parts of the city (Sunset to Ocean Beach) socked in fog, but it burns off in other parts (Mission).