I've worked outside in a T-shirt on Christmas Day once, and half-frozen to death on a mountain in summer, despite multiple state-of-the-art layers. You never know what you're in for!
I've never experienced severe cold except at high altitudes, and the wind chill itself isn't that bad - it's the rain+wind chill that's the problem. If you're wind- and rain-proofed you should be fine. I wouldn't bother with an umbrella outside towns though, they blow away.
If hiking, I take along an extra pair of trousers in my day-backpack, because, even when the weather's fine, chances are it hasn't been in the previous 24 hours, and any long grass/ vegetation will be wet, and your clothes will soak through quickly. While you wear one pair, the other can dry a little, draped over your backpack (yup, such a sexy look;) with the help of all those otherwise-irritating straps and buckles backpack manufacturers insist on. Bear in mind that denim doesn't dry very fast!
Have fun!
