This is quite possibly the most emotional time of the year. Putting all SAD issues aside, the holidays pose a number of threats, from the familial to the financial, all standing under the long shadow of excess calories, sinus infections, and recurring hangovers. On the other hand, society practically forces us to smile and party through the pain and pitfalls, to be generous and reunited, and—one would hope—to get dressed up, at least once.
For someone who came to Portland only to be shocked by the perma-casual atmosphere, the party season is a boon—I love to see how Portlanders dress festively, which, mind you, is not always translated into fancy. The slouchy reputation we have is not undeserved, but we are only beginning to get credit for how free and unique an experience it is to get dressed in this town. Unburdened by the pressures of status dressing, the stylish Portlander could have as easily procured their wardrobe from the Goodwill bins (1740 SE Ochoco in Milwaukee) as Mario's 3.10 (Bridgeport Village—17031 SW 72nd in Tigard)—or, more typically, a combination of both.
Whether or not you claim to care about fashion, the no-pressure populism of local style merits appreciation. It's not about money, much less labels (unless you want it to be), but individuality and intent. This plays out at every price point, but the local boutique renaissance we're enjoying really underscores the personality-driven code of costume, with shop owners culling lines from around the world as well as locally, based on little more than their own idiosyncratic preferences.
If you've got some scratch (hello, Oregon State tax refund), check out some of the occasion dressing options at Una (2802 SE Ankeny), where eclectic, elegant European imports rub shoulders with local Daniel McCall's studies in timeless precision. Pieces by such lines as Coven and Mociun exude personality and are rarely straightforward—it's worth taking the time to try on what intrigues you here, as many of the pieces are full of particularities that express themselves in fit. Down the street at Stand Up Comedy (811 E Burnside, #119) you'll find a small selection of intellectual lines like Patrik Rzepski, Staerk, and Rachel Comey, plus a great collection of jewelry, from necklaces of oversize ruffles (All or Nothing) to awe-inspiring crocheted metal necklaces from Arielle de Pinto and large cut-glass bracelets from Saskia Diez.
If a dress is what's needed, The English Dept. (1124 SW Alder) has great options, and if you're looking for a formal event-appropriate find, their unfussy bridal selection can often double for other black tie occasions—sift through offerings from Development, (co-owner) Elizabeth Dye, Simple Silhouettes, Vera Wang Maids, and more, plus a small selection of jewelry and the odd bolero.
As for the guys, suits and collared shirts should be standard investments, and you'll be hard pressed to end up with anything boring from Adam Arnold (727 SE Morrison, by appointment), Duchess (226 SE Madison, by appointment), or a broken spoke (2305 NW Savier). Last year I nagged that men in Portland should wear ties more often, and this year? Bowties! Find a vintage one at Magpie (520 SW 9th), the bigger and woollier the better—and don't bypass the downtown vintage staple's other accessories, from reams of costume jewelry to hats and scarves, you'll be able to channel any persona or era.
Ankle boots are still huge, for men and women, and you can find them at any price, used or new. More adventurous guys can experiment with shiny white loafers like the ones recently spotted at Johnny Sole (815 SW Alder), and heels in every color of the rainbow are a no-brainer for women, although the industry is still pushing metallics and patent leather—take it to the extreme with the sky-high patent gray Dries Van Noten wedges at Halo Shoes (1425 NE Broadway) if you dare.
...Or don't. Carry on with your nonchalance, studied or unstudied—you're still invited to the party.