With little ceremony, here we are, abruptly knee deep in fall weather. I'd like to tell you otherwise, but the sore truth is it's only going to get colder, and word is there's an icy winter ahead. Those of us who were around for Ice Storm 2004 know what that means—the only bright side is a likelihood of at least one snow (ice) day, and the bittersweet amusement of watching people banana peel onto their backs as they try to navigate the slippery sidewalks.
It also means that you need to keep warm, and sooner than planned. Go out and get something you can afford, now. Classic pairs of knee-high heels, for instance, are abundant at any price point—just make sure they fit. If they're tight on your calves, you can get them stretched, but if they're too loose and you're swimming in them, I say pass.
Besides, the thin of leg have a great advantage in working ankle boots. And even if your legs are thicker, try a few different styles. Depending on how they're sloped and cut, you could still find a flattering pair. Look for lower-cut "bootie" shapes that don't interrupt your shins for a more elongated effect, or wear an ankle boot with cigarette-cut pants to cover your bases while still showing them off.
Even if you're addicted to high heels, it's essential to have at least one pair of walking boots (else you'll bruise your butt and bust your heels during Winter Blast '07). You could also opt for a wedge, though in my opinion the only attractive wedges are too tall to be much more practical than their thin-heeled sisters.
Cowboy boots are another ubiquitous option for both men and women, and long embraced by Portland's rocker set. They're comfortable, give a little height while remaining sturdy, and aren't going anywhere anytime soon—look for boots made in Texas for the best authenticity and quality. Other gender-neutral options are variations on the Beatle boot, and engineer or biker boots, such as the ubiquitous and serviceable Frye designs.
Any shoe boutique worth its salt is going to be loaded up for the season with a slew of these options. But if you, like me, are already stressing out about cold weather's other increased expenses (heat, holidays, and hot toddies), vintage is the way to go.
A random sample of vintage stores in my neighborhood turned up mint-condition leather boots for under $50, like the supple, black, slightly slouchy knee-high '80s flats I found at Xtabay (2515 SE Clinton). And it's hard to pay a visit to the stores on E Burnside without finding something: Starting at Bombshell Vintage (811 E Burnside) and walking west, I found many cute, funky pairs of low-heeled ankle boots, such as the two pairs tucked into the tiny-but-good new vintage section of Denwave (811 E Burnside). Hattie's Vintage (729 E Burnside) has one of the hugest selections of vintage footwear in town, including an enormous number of cowboy boots for both men and women in excellent condition. Farther down, Rock n' Rose (616 E Burnside) proved less successful for boots, but their clothing is well selected, and given the prices I'd seen on footwear, I would come back for the luxurious and well-priced jackets and coats. So check out the ever-revolving goods in your own neighborhood haunts, and if the boot fits, wear it—nobody else will be able to.
If this talk of "budgets" means nothing to you, I expect to see you at the Nordstrom Runway to Rooftop benefiting PICA. See a polished presentation of the goods from the department store's via C boutique, including 3.1 Phillip Lim, Milly, Chaiken, Tracy Reese, and M Missoni. (Wieden+Kennedy, 224 NW 13th, Sat Oct 6, 6:30 pm, $100)
Get the boots: email@example.com