Summer in Japan can be very enjoyable, but you should plan your wardrobe accordingly. June and early July is the rainy season. The Japanese call it Tsuyu. If you don’t like the rain, you should probably either travel in the spring, later in the summer or in the fall. During this time of the year, it really does rain every day. You may want to bring some rain gear, some water resistant shoes, and maybe an umbrella. If your primary interest is the island of Hokkaido, then you’re fine. There is no rainy season there.
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If you wait until mid-July through August for your trip to Japan, you will need to plan for hot, humid weather. You may find fewer crowds in Tokyo because many travel to Hokkaido for the cooler weather at this time of year. Bring clothing that will keep you feeling cool and refreshed. Choose thin natural fabrics that will breathe well. Swirly skirts are more comfortable in the heat than pants.
You may want to bring a light sweater, as most places have air conditioning and it may get a little chilly from time to time. Casual wear is just fine for many of the clubs and shops that you may want to visit. If you are planning on doing any clothes shopping while you are there, they will be perfect to wear while you explore the city.
The average high temperature in August is in the upper 80s, so you can expect some higher temps as well. The best thing you can do is pack clothes that make you comfortable in sweaty weather, and try to stay indoors for the air conditioning when you can.

