hmmm... I would buy a nice pair of shorts and leg warmers... maybe another pannier
1. Schwalbe winter (studded) marathon tires 700c x 35: $150
2. Fenders for 700c x 35 tires: $20
3. 3 Ankelites: $60 (two for ankles, one for left arm for turn signals) - though I should probably just try one and see how I like it.
I would not go on a bender with Zen as fun as it sounds. I would like to see if I could find a pair of insulated boots for riding.
Yesterday I spent $286.00 on cold-weather clothes that will work for both XC skiing and cycling. I got a great pair of pants and matching jacket by Salomon. The pants are awesome - they're flared at the bottom, like I wanted for skiing, but you can snap them to make them tapered for cycling. I love that techy material - so lightweight and stretchy but warm and wind-resistant. It's all black. If it werent' for the reflective trim, I'd be "Bike & Ski Ninja"! If I'd had a $250 gift card that's what I would have got yesterday.
Now that I already have those clothes, if I had $250 I would get some good gloves, a nice thin hat to go under my helmet, clipless pedals with shoes, and some great socks.