Anyone who's ever worn a pair of jeans knows that Levi Strauss may have invented jeans but the Japanese perfected them. Where would we be, really, without their 1990s-era embrace of selvedge denim?

But the truth is that the Japanese’s fascination with mid-century Americana goes far beyond jeans. This fixation is, depending on how you look at it, either perfectly understandable or just a little perverse: America, after all, occupied Japan from 1945 to 1952, following the country’s defeat in World War II. It was a disorienting period of recalibration for the Japanese, who lost not only the war but, for a period, their sense of self—something they wouldn’t recover until the 1960s, when the country underwent its startling transformation to modernity (and then, in the ’80s, hyper-modernity).

What’s inarguable, however, is that the Japanese have always been obsessives . . . and what’s more, once they become obsessed with something, they invariably improve upon it: a lesson that style writer and professional bon vivant David Coggins learned decades ago, as a freshly minted college graduate, on his first of many visits to Japan. “I’ve always collected classic men’s clothes,” says Coggins, who’s a creative consultant for Freemans, the New York City–based fantasyland of men’s style. “I actually bought shoes—without even knowing if they’d fit—from Douglas Fairbanks, Jr.’s estate auction.” But in Tokyo, Coggins discovered people whose dedication to American nostalgia eclipsed even his own—be they vintage-store owners selling beautifully preserved World War II Army jackets or tailors dedicating themselves to re-creating the perfect RFK-era sack suit. And so we asked him to share with us his favorite time-travel destinations in Tokyo: places where even the most die-hard nostalgist would find himself wondering if he hadn’t, somehow, traveled back in time.

Left: Shirt collars at Caid Modern Tailoring. Right: Whiskey on the rocks at the Orchid Bar. Kohei Take

Orchid Bar

When the Okura Hotel opened on the edge of Roppongi in 1962, it was a modernist sensation: Designed by architect Yoshiro Taniguchi, it quickly became a symbol of the country’s leap into the postwar decades of rapid wealth and globalization. Today, the Okura is a luxury hotel, but despite the changes visited on both the hotel and the city, its iconic Orchid Bar remains untouched. With its low ceilings, wood accents, and discreet stained glass panels, the Orchid—which has just 15 bar seats—still recalls a more civilized age of travel. But aside from the soothing atmosphere, the real reason to come here is the whiskey. The entry to the bar takes you past a series of 20-odd glass lockers stocked with longtime customers’ extraordinary collections (I saw a bottle of 1971 Macallan, which might fetch $10,000—if you can find one for sale), and once seated, you can order whiskey of varying ages: a 17-year-old Hibiki, one of Japan’s finest, is about $20. If you take it on the rocks, your drink will be poured over a perfectly round orb of ice the size of an orange (2-10-4 Toranomon, Minato-ku; hotelokura.co.jp).