Tokyo in October: 22°C / 72°F afternoons, 15°C / 60°F mornings, 235mm of rain across 12 days — the wettest month of the year.
The rainy season everyone plans around is the wrong one. Japan Meteorological Agency (JMA) normals put October at 235mm across 12 days, ahead of September's 225mm and well past June's 170mm, which makes October the wettest month of Tokyo's year. The temperature is the easy part: 22°C / 72°F afternoons and 15°C / 60°F mornings ask for one light layer and nothing more. The hard part is 4 hours of sun a day, so anything that soaks through stays wet until tomorrow. Pack for drying rather than for warmth. Tokyo itself is set up for this: every conbini sells a clear vinyl umbrella for about ¥700, and shop doorways hand you a plastic sleeve for it.
October is the wettest month on Tokyo's calendar. Not the June rainy season everyone plans around — October.

The only warmth layer October needs. Mornings sit at 15°C / 60°F on an open platform and afternoons reach 22°C / 72°F, which is a single-knit gap rather than a coat gap. Wide-rib cotton-blend over wool: it dries faster in a city getting 4 hours of sun a day, and it comes off without wrinkling when a train carriage runs warm.

For the nineteen or so dry days. A clean straight leg with no distressing takes a flat shoe through Omotesando and a restaurant in Ebisu the same evening, and the cuffed hem sits above a wet pavement rather than wicking it. Denim is the wrong call on the twelve wet days, which is why the dark quick-dry trouser below is the other half of this slot.
Cream rib knit · light-wash straight-leg jeans · water-resistant flats · packable shell in the bag · zip crossbody. Coffee in Nakameguro, then Omotesando before the afternoon rain.
Same knit · dark quick-dry trousers · flats · shell worn · light scarf. A 19:00 table in Ebisu, umbrella in the stand at the door.
Per Japan Meteorological Agency normals for 1991–2020: the average daily maximum is 22.2°C / 72°F, the average minimum is 15.3°C / 60°F, and the monthly mean is 18.7°C / 66°F. Rainfall averages 235mm across about 12 days, with roughly 4 hours of sunshine a day. That makes October the wettest month of Tokyo's year, ahead of September at 225mm and well past the June rainy season at 170mm. October also sits at the tail of typhoon season.
No, and this is the most common October misunderstanding. Tokyo's kōyō, the autumn-colour season, does not peak in the city until late November and into early December, roughly a month after most visitors expect it. October in Tokyo is green, wet, and mild rather than red. If autumn colour is the reason for the trip, book late November for Tokyo itself; the mountains west of the city and the higher-altitude areas turn earlier, from mid-October.
A packable hip-length rain shell, one light knit, two bottoms (one denim for dry days and one dark quick-drying trouser for wet ones), water-resistant flat leather shoes, a light scarf, a small zip-top crossbody, and no umbrella at all. Buy the clear vinyl compact from any convenience store for about ¥700 on arrival. Skip suede, canvas, and white trainers. The temperature range only asks for one warmth layer; everything else in the bag is about staying dry.
Buy one there. Every convenience store sells a clear vinyl umbrella for roughly ¥700, they are genuinely ubiquitous, and it is a better use of luggage space than packing your own. Choose a compact rather than a long one: full-size umbrellas are awkward on a rush-hour train, and most shops, museums, and restaurants provide a stand or a thin plastic sleeve at the entrance so you are not carrying a dripping umbrella indoors.
October is cooler and marginally wetter. JMA normals put September at 27.6°C / 82°F by day and 20.8°C / 69°F at night against October's 22.2°C / 72°F and 15.3°C / 60°F, so September is still a genuinely hot, humid month while October is mild. Rainfall is close, at 225mm against 235mm. The practical difference is the layer: September needs nothing over a single light top, October needs a knit for the morning and a shell for the afternoon.
Neutral, covered, and quietly precise. The October street register is a light knit or a long-sleeve shirt, a tapered dark trouser, a flat leather shoe, and a shell or light trench carried rather than worn. Colour stays low: navy, charcoal, stone, black, with the occasional deep brown. Legs and shoulders are generally covered, shorts read as summer-only, and a clean flat shoe matters more than a statement one because everyone is walking and standing on wet ground.