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.