Imagine if we lived in a season-less, controlled temperature environment, and you could forget about what month is on the calendar and just wear whatever you wanted—sweaters in July, bikinis in January. While somewhat appealing, I wonder how many would bundle up all the time, relieved not to have to deal with a "swimsuit season," and how many would run around with their asses constantly hanging out.

But you need not become so vexed. Summer is your excuse for skimpy (if you need one) and winter for hiding in layers (again, if you feel excuses necessary). And hello, winter is most definitely gaining upon us. I've already put holes in no less than three (three!) of the pairs of tights I dutifully stocked up on, and still haven't gotten around to updating the buttons on last winter's coat to make it feel new again (probably futile).

There's just no getting around it: A winter shopping spree is in order. And I know it might be a little controversial for some of you stalwart Portlanders, but get a goddamn umbrella. Yes it most certainly does rain hard enough here to justify it. But if you still insist on refusing sensibility, consider a nice hat. Pinkham Millinery (515 SW Broadway) has a range of beautiful caps, fedoras, cloches, and more in a sturdy, soft felt (ask creator Dayna Pinkham how long she's worn some of her hats, and you won't believe how well they've held up, even with minimum maintenance and maximum manhandling). Starting at just over $200, they're an investment, but a solid one.

Pin Me Apparel (3705 N Mississippi) has everything from puffy, snow-ready styles to Audrey Hepburn-esque classics at reasonable price points. But if you're feeling flush, by all means splurge on a gorgeous coat from Mackage, designed in Montreal. Available through Le Train Bleu (, pre-order yours now, and it should arrive by the time they open their new location on November 24 (748 NW 11th). (My favorite is the one pictured here.)

For what to wear underneath, clearly cashmere is the most desirable option, and Souchi (807 NW 23rd) is where to find it (look out for Thanksgiving weekend sale kicking off on November 24—for details on what kind of savings you'll enjoy, stop on by). One more word of advice before you go out in this weather: Have all of the leather soles on your shoes covered with a very thin layer of Vibram rubber. Any cobbler can do this for you lickity split, but the most shoe-obsessed in town rely on Rubio's (115 SW Ash).

Must... not... hibernate...