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Tokyo’s Cutting Edge

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Launch Slideshow
Photo: Andrea Fazzari

Sunaokuwahara

Ethereal garments hang from the racks of this large shop; but for the sun pouring in it would feel like a grotto. Sweatshirts are feminized with dropping flower appliqués; a ruffled, gauzy peach dress ($393) is as wispy as a dandelion.

Colour by Numbers

Owned by the same team that runs Loveless, and decorated with similar insouciance: you're greeted at the door by a pair of taxidermied rabbits balancing on a soccer ball. Inside are sneakers studded with nail heads alongside a plaid jacket with bondage straps—and a built-in backpack.

Naked Bunch

Elegant despite its name, this long, narrow glass-fronted shop specializes in pieces by self-taught Japanese fashion designer Ed Tsuwaki. Canvas slip-ons are decorated with carefully drawn antelopes; tunics are patterned in clean black and white stripes.

Merceria Pulcina

On sunny days, the irresistible tidbits from this tiny dry-goods shop spill out onto its front patio. Along with spools of ribbon and lace, there are remnants of vintage children's fabric, some of which have already been made into little tote bags.

CA4LA

Rough brick walls and antique table lamps sitting askew on the floor make this hat emporium feel like a deconstructed general store. There's everything from trapper hats and furry fedoras to scarlet fur-felt Borsalinos ($166), Stephen Jones berets that say TIME TRAVEL, and chapeaus for any gender, every taste.

Nakameguro

This bohemian neighborhood is named for the canal that runs through it; in cherry blossom season, falling petals turn the water a breathtaking pink. This is the anti-Ginza: you won't find any big names in the boutiques that line both its banks.

Toll Free

The witty collection includes clothes by the eccentric English designer Paul Harnden, who prides himself on 19th-century detailing, plus men's vintage wristwatches and faintly sinister gloves that instruct wearers to "insert trigger finger."

Per Gramme Market

A big messy vintage-clothing store that's young, cheap, and fun to dig through. If you have your heart set on a vintage kimono, there's a rack of them here, starting at a wildly affordable $34. Schoolgirl kilts are $25, and there's even a big section, believe it or not, of well-worn cowboy boots.

Cow Books

The owner of this shop rides around Tokyo dispensing his wares from a bookmobile. A Jenny Holzeresque LCD ticker running around the ceiling reads TAKE A COFFEE GET SOME FEELING; left-wing political tracts and Beat Generation tomes are among the specialties, but there are also Olive Oyl comics in Japanese, as well as vintage Vogues. The store's slogan, everything for the freedom, is emblazoned in red on white denim jackets and carryalls that close with little bows ($131).

Waingman Wassa

Though its windows face the canal, you enter this shop by walking through a dark parking lot where unlocked bicycles, themselves providing a cultural shock, are neatly lined up. The merchandise is a mix of the practical (industrial mailbags) and the ethereal (a shredded georgette dress worthy of a supercool Miss Havisham).

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