The owner of Cannibals, Pamela Springfield, has three criteria for the pieces she displays at her art gallery: They have to have been made within the past year (no art-school theses, please), within a gas tank or bike ride of the gallery, and at least partly of recycled materials—hence the name. Her rules have winnowed the selection to a weird array of art; one piece recently showcased in the gallery's windows was a "turkey" Frankensteined from a doll head, glove-fingertip feathers and taxidermied bird feet. Prices, like Cannibals itself, fall somewhere between art-gallery and secondhand store.

Sci-fi ray-gun sculpture by Mark Counts.

Think you can't pull off a hat? Pittsburgh-based hatmakers Goorin Bros. are out to prove you wrong. The company's Portland store peddles almost every style of headwear, from ski-bum beanies to Don Draper fedoras. Speaking of: Don the befeathered Pauly fedora and you'll cut as classically stylish a figure as any of the boys at Sterling Cooper. Goorin's prices aren't low, but neither is the hats' quality, and panache is priceless.

Felt bowler ($49).

A jet-black, crotch-high Great Dane stands guard at the door to Tibetan Fox, but enter anyway; the store's dog, Rav, is friendly, and its screenprinted tees are stylish and frequently clever. Tibetan Fox prints its designs on American Apparel shirts, using colorful, ink-stained machinery right in the store. For a reasonable price, it'll custom-print in your choice of shirt and ink color. Have some graphic-design chops but not screenprinting savvy? The store will even print your own design on anything.

Winston Churchill T-shirt, $25.

From chic clothing to chichi housewares, there's no shortage of pretty, pricey stuff on offer in Nob Hill. If you've got the dough for it, go for it. But if you're like the rest of us poor folks, head for William Temple House. It's a Goodwill-class thrift store; nobody's jurying the selection, but it's well-organized and, most importantly, cheap. A bonus is the store's robust furniture section—a rarity among Portland secondhand shops.

A record, a jacket, a couch.

You know what they say about guys with big feet: It's hard for them to find shoes that fit. See, most footwear companies don't make shoes in large sizes, leaving the big-footed but fashionable with specialty shoes, or whatever they can find at discount department stores like Ross.That's why Seth and Zac Longaker—gigantesque brothers who both wear size 16 shoes—started Oddball, a company whose noble mission is to shod those trod upon by shoe-market forces. Oddball provides brand-name shoe companies like Adidas and Vans incentive to make their products in sizes 13 through 18 by giving them access to their niche—but international—customer base. The company has a storefront in the off-the-beaten-path Slabtown 'hood, but sells kicks through its website to customers around the world. It's a win-win-win situation—for the big shoemakers, for Oddball, and for the poor, clown-footed souls to whose step the company is returning some spring. Oddball's customers include, perhaps unsurprisingly, pro basketball players, but the store's staff, frustratingly respectful of their clientele's privacy, were mum about exact identities. A b-ball player yourself? Try on a pair of old-school hoops shoes, like PF Flyers high tops or Nike Blazer SBs.

Six-pack of Oddball XXL crew socks ($27).