The Insider's Guide to Tokyo: Retro Designers, Listening Rooms, and the Most Stylish Accommodations

      Welcome to Who What Wear Travels, a series of curated guides to destinations adored by the fashion crowd. This is your go-to source for everything from the most stylish accommodations to unforgettable dining experiences and ideal travel wardrobes, all approved by fashionable locals and seasoned travelers. Among all the places on our travel wish list, Tokyo remains a top contender. Few destinations are as universally adored. Just ask anyone who's visited recently, and you're bound to receive an enthusiastic response—whether they're food enthusiasts, vintage fashion aficionados, culture lovers, or others. One thing we've learned from our own excursions to Tokyo is that whenever you mention your trip plans, you're likely to be inundated with passionate recommendations. Everyone has a strong view on the subject. This enthusiasm stems from the endless possibilities offered by the city (it's the size of 37 Manhattans!), making every visit unique. While there's never a bad time to talk about going to Tokyo, the excitement continues to mount among American travelers, prompting us to present our comprehensive yet non-exhaustive Who What Wear travel guide to this vibrant city. With insights from fashion insiders—including Elie Inoue, a fashion journalist based in Paris but originally from Japan; Diana Tsui, a Substack writer and the digital lead at 10 Magazine U.S.; and accessories designer and Tokyo expat Poppy Lissiman—as well as my own experiences, consider this your essential guide to the best places to stay, eat, shop, and explore in Tokyo, all through the lens of style.

      **When to Visit**

      Spring is undoubtedly peak season due to the cherry blossoms, but Inoue shares her preference for autumn, particularly October to November. "Unlike Europe or the U.S., where fall can be quite rainy, Japan typically enjoys clear skies and moderate temperatures during this time," she explains. "Furthermore, the environment transforms into breathtaking hues of red and yellow, with autumn leaves and golden ginkgo trees creating a particularly beautiful backdrop." The weather during both spring and fall is generally pleasant and ideal for sightseeing. The only time to avoid? July and August, if possible, according to Tsui, since the heat and humidity can be oppressive, making it challenging to explore on foot.

      **Where to Spend Time**

      For first-time visitors, Tsui recommends Shibuya, Shinjuku, and Ginza as safe choices, along with Roppongi and Toranomon. "These areas host the majority of well-known hotels, with Roppongi, Ginza, and Toranomon leaning towards luxury while Shibuya and Shinjuku offer more budget-friendly options," she notes. "For shopping, Shimokitazawa, Koenji, and Nakameguro are also very enjoyable, especially if you're in search of traditional vintage items like denim or deadstock pieces from Calvin Klein, Ralph Lauren, and Burberry." For a deeper dive, Inoue suggests Yoyogi-Uehara and Yoyogi-Hachiman as personal favorites. "This neighborhood is popular with locals and features a variety of unique shops," she explains. "Shimokitazawa has long been a favored spot for vintage shopping and experiencing local life, but in recent years, more savvy travelers have started exploring Koenji. I suspect Kamata might soon be the next neighborhood to gain attention."

      **Where to Stay in Tokyo**

      *Image credit: Aman*

      **Aman Tokyo**

      Few hotels across the globe exude as much celebrity allure as Aman Tokyo. Its launch marked the hospitality brand's first urban establishment, seamlessly combining a Japanese-inspired aesthetic with the renowned ultra-lux minimalist design of Aman. Located on the upper floors of the Otemachi Tower in Tokyo's financial district, the sleek and spacious rooms provide sweeping high-floor views, though the extensive multi-level spa remains the hotel's standout feature.

      **Bulgari Hotel Tokyo**

      Recognized as the top hotel in Japan and ranked 15th among the World's 50 Best Hotels, the Bulgari Hotel Tokyo fulfills its luxury pedigree in every aspect. While nestled in the capital's heart, just steps from Daimaru Tokyo and Tokyo Station, the property is marked by its unparalleled exclusivity, privacy, and intimacy, making it a true urban sanctuary. In terms of design, the hotel unites a sophisticated mix of contemporary Italian style with elements of Japanese tradition, blending the rich legacy of Bulgari's design codes with local craftsmanship and culture.

      *Image credit: Trunk Hotel*

      **Trunk (Hotel)**

      If you want to immerse yourself in the bustling Shibuya shopping district, fashion aficionados universally recommend Trunk. "A boutique hotel that embodies modern Tokyo's essence," Inoue describes this community-oriented spot located right on Cat Street. "I had the chance to visit during a fashion event, and it genuinely felt like a place to soak in the city's creative vibe. In contrast to another favorite of mine, Hoshinoya Tokyo, which showcases a more genuine and traditional Japanese design