One thing you need to know about me? I refuse to check a bag when traveling. The airport is stressful enough as it is, and I’d rather forgo the long check-in lines and heavy luggage to have my Away carry-on by my side through the whole journey. No AirTags here! So when I booked a 10-day vacation to Japan, I was already up for the travel wardrobe challenge. Summer always makes the task easier (no thick sweaters or chunky boots needed, of course), so I opted for lightweight T-shirts and tops that I could mix and match with various shorts and skirts.
Also, I had never been to Japan before and knew there would be miles of walking ahead of me to fully explore everything. Keeping that in mind, I almost entirely depended on my Adidas Sambas and Salomon sneakers to get me through all the steps. The first leg was spent staying at the Ritz-Carlton Tokyo in Roppongi, which is between the trendy, buzzy area of Shibuya and the upscale neighborhood of Ginza. Kyoto was the next destination thanks to the high-speed bullet trains, and it was even hotter there (like 95ºF) than in Tokyo. Below, I rounded up the 22 items that held up through the heat and endless walking. If you’re planning a similar trip soon, you have permission to steal my itinerary.
On day one, Shibuya was the first stop from the hotel, and I went with this breezy Dôen blouse, a black maxi from Urban Outfitters, my Sambas, and a paracord shoulder bag from this handmade brand I recently discovered called Tumbleweeds.
Cat Street is definitely where you want to be when all the stores open at 11 a.m. There is everything from thrift shops and secondhand luxury resellers to staples like Levi’s and Patagonia. You can start walking on this street in Shibuya and follow it north into Harajuku. Some of my favorites were Ragtag, BerBerJin, United Arrows, Maidens, and the countless Beams stores.
I threw this simple black Free People number into my suitcase in case a dinner called for a dress, and it’s one you can elevate with loafers or wear casually with sneakers. (I opted for the latter.) The halter neck and open back really helped with the hot weather.
This izakaya called Tatemichiya had a bunch of punk rock posters and a loft area with extra floor seating. You’ll have to take your shoes off in certain establishments, so a good rule of thumb in Japan is to wear socks unless you want to be barefoot in public places. Not me! The below pack of Hue socks was one of the best purchases I made before the trip.
An oversize T-shirt always speaks to me, so I had to pack this Simon Miller Bird Club shirt. I paired it with some Adidas shorts, white Salomons, a red pair of Garrett Leight sunglasses, and my favorite Marge Sherwood bag for a day walking around the Meiji Jingu shrine. Jewelry-wise, I had my yin-yang Susan Alexandra earrings and La Manso ring to accessorize.
This outfit took me from fluffy pancakes at Micasadeco & Cafe for brunch to Golden Gai in Shinjuku well after midnight, so I’d say it was very versatile.
South of the hotel is Meguro City and Onibus Coffee, which was one of the best coffee shops in the whole trip. The neighborhood has tons of cute shops that are next to the Meguro River—a more relaxing change of pace from the previous days. I went with a loose-fitting top from Mother Denim, utility shorts from RTA, Vehla sunglasses, Plasticana garden clogs, and a handy plaid tote I bought there. In hindsight, the clogs were a bad idea since they have very little support, but I was tired of wearing the same two sneakers! Below, I added clogs that are probably a little more comfortable for those 10,000-step kind of days.
The first few days were spent exploring spots farther from the hotel, so I wanted a day to take in the nearby area of Roppongi and see the Tokyo Tower. Also, if you’re looking for a solid slice of pizza for lunch in this area, Savoy Tomato & Cheese was a winner. I bought this shirt from Hollywood Ranch Market in Daikanyama and rewore my black maxi skirt for a more laid-back day.
For dinner at Narukiyo Izakaya, I went with this printed mini from Dôen. Though it’s slightly sheer, the thinner material was ideal for the sweat-inducing temperature. Izakayas are usually casual spots, but this one was a tough reservation. (Dua Lipa said she’s “obsessed” with it in her newsletter, FYI.) The Ritz arranged it on our behalf, so if you’re planning to visit, definitely lean on your hotel concierge to help book any restaurants. Many spots only take reservations over the phone, so it helps with the language barrier.
After recharging at the hotel, Kyoto was the next city to visit. It’s about two hours via the bullet train, and to gear up for another full day of sightseeing, I wore my comfy Adidas shorts again along with an embroidered top from Made Some Souvenirs and Salomons. Nishiki Market, Gion, Pontocho Alley, Maruyama Park, and walking along the Kamo River were some highlights.
The Arashiyama Bamboo Grove was at the top of my list, and I went for a very simple outfit since this was one of the hottest days by far. I wore this Goldie T-shirt, the same RTA shorts, and Ray-Bans to wander around the grove and the surrounding town. My advice is to go to the grove early in the morning to beat the crowds, and then you can spend the rest of your time grabbing coffee at Arabica, visiting the monkey park across Katsura River, and walking around the nearby temples.
Another temple, another trek, but Fushimi Inari is one of the most iconic in Kyoto thanks to the thousands of red torii gates that wind up Mount Inari. These boxer shorts from Remain Birger Christensen are ones I always bring on trips because they can roll up so easily. I brought back my Dôen shirt, Sambas, and Marge Sherwood bag for the trek to the top—and grabbed a shaved ice dessert on the way down to cool off.
