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Outerwear in September

Wife and I are heading to Prague in mid-September. Flying over with carry-on only for 5 days.

Any recommendations on our one outerwear? Fleece, windbreaker, rain jacket, or?

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Depends on weather, average high is in the 60sF, low in 40s. Assuming you don’t hit unseasonably warm or cool days think what you’d be comfortable in with that temp.
But you need to be prepared for rain. I don’t think it’s a very rainy month but rain is always possible.

I don’t like fleece in rain so I’d go with a water resistant light jacket with a hood. For city travels high-tech waterproof gear is overkill. Just a trench coat or windbreaker would be my choice. Which depends on style. If you are going to theater/opera/fancy restaurants you would want a nicer trench style coat. If you are keeping it casual then a more outdoorsy/athletic windbreaker is fine.
I don’t like umbrellas abd rely on hoods in rain so that would be a key feature. I always forget my umbrella, or don’t use it because I’m short and it would hit passers by.