214 SW 8th Ave., 827-3300
My gripe with a lot of hipster boy clothes is that they seem to come with a lifestyle built in, some unholy DJ-swinger apparition that already wore the clothes and stunk them up with Bacardi Breezers and Joop! cologne. Lit's inventory, peppered with careful picks from smart brands like Modern Amusement and Religion, does what cool clothes should do--give the buyer the impression that he is making a creative choice, not just buying into someone else's scene. Winning pieces sell out in a flash, so you could visit semi-weekly and see something new. What's more, owner Kenny Wujek's warm, unpretentious manner completely takes the sting out of shopping.
128 SW 3rd Ave., 294-0445
Long the champ in Portland for global indie clothing (reaching as far up the food chain as Marc Jacobs, as far afield as Fornarina, and as far out as L.A.'s Grey Ant), Poker Face recently got national props from FHM magazine as one of the best men's boutiques in the nation. Don't be scared off by the plastic backpacks and riot of Gola sneakers at the front--PF isn't just for foreign exchange students and record-store employees. Besides stocking unusual labels and one-offs, PF's sale rack has some of the best markdowns in town. Be warned: Customer service can be--um--uneven. My advice: Wear nondescript clothing, speak to no one, and bury yourself in the racks.
606 SW 9th Ave., 223-9252
It's been eight years since Brent Collier first broke the seal on his super-secret style venture, which brings pallets of past-season couture and high-end apparel directly from New York and Italy stock houses to Puddletown. In 2002, his new shop (behind the Rich's Cigar Store on Alder) gained a visible presence (a readable sign, a sandwich board, regular hours). The main floor offers classic men's pieces (Daks London wool and cashmere sweaters for $125, D&G corduroys for $145, odds and ends from Versace, Prada, Jil Sander), while the basement "Bottom Line" stocks scrappier streetwear from Diesel and Miss Sixty, as well as the store's mega-redlines.
1425 NE Broadway, 331-0366
Owner Nathan Newell goes beyond paying his dues at those depressing Vegas shoe-buying shows--he also travels directly to the ancestral birthplaces of cool treads (Italy, Spain, France) to stock his small but selective boutique. Halo is the shoe lover's equivalent of your favorite indie record store--you won't find the latest Counting Crows album there, but you don't want the latest Counting Crows album. For uniqueness, craftsmanship, style and quality, these are simply the best men's shoes in the city.