We Asked a Fashion Editor and a Stylist What To Wear and Not Wear in Tokyo

If you’ve read any travel destination guides recently, you’ve likely seen Tokyo at the top of the lists—and it makes sense. The Japanese capital offers visitors a perfect blend of ancient traditions and futuristic innovations. Beyond the temples, Shibuya Crossing, and the skyscrapers, what truly draws travelers, specifically the style set, is the fashion. It’s not just about the incredible vintage shopping or the designer boutiques, but also the street style. That’s why, likely once a month, someone on your Instagram feed posts photos from there and may have successfully convinced you to book a vacation. If that’s the case and your trip is fast approaching, with outfit photos already on your mind, you’re exactly where you need to be.

With Tokyo still firmly at the top of my travel wish list, I decided to seek out guidance on what to wear and what not to wear in the city. I turned to two seasoned fashion insiders, individuals who don’t just visit Tokyo but truly know the city and its style ethos. These experts are Who What Wear associate features editor Ana Escalante and consultant, stylist, and writer Diana Tsui, who shared their most insightful advice on navigating packing. Their focus is on dressing with intention, keeping practicality and comfort top of mind.

“I’ve been to Japan a total of eight times over the last decade—one of my stays lasting over a year as I lived my Kawaii girl fantasy in Tokyo—so I know a thing or two about what to wear in Tokyo (and, most notably, what not to wear),” Escalante says. For starters, Escalante shares that Japanese and Tokyo style is all about practicality. “I always try to tailor my style when I’m over there so I don’t stick out like a sore thumb,” she says. “Neutral colors, easy basics, and baggy, oversize silhouettes are the name of the game, whether you’re exploring Kichijoji or getting late-night sushi in Shibuya.”

When it comes to footwear, Escalante and Tsui agree that comfort is key. You’ll be doing a lot of walking—”20,000 steps easily,” says Tsui—and you don’t want to end up out and about all day exploring, only to regret your shoe choice. “I lived in my Cecilie Bahnsen x Adidas as well as my Nike Muse sneakers when I was there,” Tsui says. Beyond sneakers, Tsui and Escalante note that ballet flats like Maison Margiela Tabis, loafers, or sneakerinas will also keep you comfortable and looking chic. “Otherwise, you actually don’t need too much—not even pajamas, as most hotels offer them,” Tsui adds.

Keep scrolling to discover the five specific trends to avoid in Tokyo and what to wear instead.

Wear: Relaxed Jeans

Skip: Skinny Jeans

Ease is everything in Tokyo, so while there is chatter about skinny jeans making a comeback, the style set there continues to wear relaxed denim. This means loose straight-leg jeans or fully baggy styles. Beyond being the fashion-forward choice, anti-skinny jeans also offer comfort for long days spent navigating new neighborhoods.

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Wear: Flat Shoes

Skip: Heels

“Despite being a heel-lover, I refuse to wear anything but flat, comfortable shoes in Tokyo,” Escalante shares. “You might be able to get away with kitten-heel pumps if you aren’t walking far, but you may come to regret it.” That said, make sure to pack ballet flats, mules, elevated slippers, or loafers—pairs that you’ve worn before and know don’t cause blisters. Ahead shop the chicest styles on the market right now.

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Wear: Long Coats

Skip: Cropped Jackets

If you’re heading to Tokyo during the cooler months, when you need outerwear, avoid cropped jackets and opt for longer styles instead. Options include a car coat, trench coat, long shearling jacket, or a quilted design. While printed patterns like leopard, stripes, or plaid are nice, a solid-colored, streamlined jacket is more versatile and easier to style. If you’re visiting from late April onward, when Hsui notes it becomes very humid and hot, you might want to leave the jacket behind.

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Wear: Technical Sneakers

Skip: Platform Sneakers

Sneakers are a safe bet if you plan to be on your feet all day. However, don’t bring just any pairs. The styles trending right now in Tokyo and many other places around the world are technical sneakers. These feature performance-driven silhouettes and details like toggle fastenings, lug soles, and a mix of mesh and leather. Many are hiking and trail shoes, such as Salomon’s XT-6 sneakers and Alo’s new Trail, but don’t worry, they extend far beyond uneven terrain, to fit street-style moments, paired with denim, trousers, or a skirt.

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Wear: Drawstring Pants

Skip: Culottes

Another easy and versatile yet elevated basic to pack for your trip is a pair of drawstring trousers. These pants come in a wide range of luxurious and practical fabrics—whether you opt for linen or cotton for summer travel, or satin or a knit blend for cooler seasons. This variety ensures they can be dressed up with a leather jacket and heels or dressed down with a sweater and flats. Plus, they make packing easy because they fold well, minimizing bulk and weight.

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