If Harajuku is the youth-oriented fashion capital of Tokyo, then the Omotesando and Aoyama areas are the mature, sophisticated older sibling. Filled with high-end fashion boutiques, groundbreaking design houses, and perhaps the fanciest cafe culture in all of Japan, spending a lot of time (and a lot of money) is easy to do when visiting this trendy pocket of the city.
The main avenue of Omotesando is located outside Omotesando Station on the Chiyoda metro line.
If you're traveling via the JR Yamanote line, get off at Harajuku Station and take the scenic walk down the tree-lined boulevard just to the right of Harajuku's main drag, Takeshita Dori, and you'll find Omotesando.
Some consider it an offshoot of Harajuku, or part of Harajuku itself, but Omotesando's high-end shopping and tucked-away designer stores separate it from the bold, candy-coated streets of Harajuku's Takeshita Dori. The cosmopolitan street is often compared to Paris's Champs-Élysées, and its crowning jewel is the Omotesando Hills shopping complex.
If shopping were a sport, then Omotesando Hills would host the Olympics. Designed by famous Japanese architect Tadao Ando, best known for Church of the Light, the massive open halls are sometimes called the "Omotesando-within-Omotesando." With over 75 stores that sell the latest high-end clothing, beauty products, and accessories, as well as exhibition spaces and a floor of cafes and restaurants, there's something for everyone under this carefully designed roof.
Moving out into the open and across the boulevard; it's time to check out Cat Street. Though not a street filled with cute kittens (you'll have to go to neighboring Harajuku for those), Cat Street is the runway through which the area's fashion-forward youth show off their looks while searching for the next.
Running from north to south through the middle of Omotesando and Harajuku, this street is often considered the retail and design heart of the area. Though it does house some of the biggest names in contemporary fashion, one shop you can't miss in the area is RAGTAG. A local institution, this store is home to some of the best vintage and new Japanese-brand designer wear you'll be able to find anywhere in the world. If you're chasing a special Issei Miyake piece or want to get ahold of some Comme De Garçon on the cheap, a trip to RAGTAG is recommended.
What good is shopping for stunning fashion if you can't show off your recent purchases in public? Offering a wide selection of international and local options, a visit to the high-end suburb isn't complete without a luxurious cafe treat to really enhance the Parisian vibe.
With al fresco dining aplenty, Omotesando's streets are the perfect spot to people-watch and fashionista-spot when the sun is out. For great coffee, don't miss out on Oakland-implant Blue Bottle Coffee, and for French cuisine with a Japanese twist check out Aoyama Flea Market Tea House. Omotesando is also home to the Tokyo location of Paris-favorite Coutume and Norwegian original Fuglen.
As the day rolls on into the evening, make your way to open-air food court and occasional live music space Commune 246, where the rotating cast of food trucks and mini-bars offer everything under the sun (quite literally).
Though Tokyo is one of the most densely urban areas in the world, the city still manages to squeeze in green spaces and open-air events. Walking from Omotesando crossing towards Shibuya you'll find a farmer's market nestled on the grounds of The United Nations University.
Featuring some of the finest produce from the wider Kanto region, the market is open most weekends from the early morning. The site also seasonally hosts the famous Coffee Festival, which sees caffeine connoisseurs line up to taste the best brews the world has to offer.