A: I've got just the thing for you—the Nolita Jacket from Ibex ($240; www.ibexwear.com). It's a very stylish but fully functional jacket that's made with a heavyweight but soft loden wool that works wonderfully in cool and wet weather. And, it doesn't look at all dorky. I will say it doesn't have a hood, but any number of hats would work well with it—personally I prefer hats to hoods, anyway. Layer it up in really cold weather with Ibex's Woolies Zip T-Neck ($62).

For really lousy conditions—and Chicago can produce them, heaven knows—L.L. Bean's Baxter State Parka might be the ticket. It's down-insulated and Gore Tex-lined, to withstand snow and wind, and its full hood has a zip-off synthetic fur ruff. Plus, at $209 it's an excellent buy (www.llbean.com). Bean has shaped it for women and offers colors that aren't camo, but it still has a certain hunting-garb appearance that may or may not be suitable. Maybe a little more fashionable would be Patagonia's Puffski Jacket ($300; www.patagonia.com), which is designed as a ski piece so has an outdoorsy look with a bit of panache. Its PrimaLoft insulation is warm, soft, and durable, and the Puffski has a waterproof-breathable shell—plus a full hood. Very warm and not at all bad-looking as you're waiting for the number 33 bus to take you to class.

For more stylin' gear, check out Outside Online's all-new Guide to Urban Wear.