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Any tips?

There is a wedding as well, and I'd like to do minimal packing. All I know is blazer and dressier pressed khakis are going for certain. Medium brown wingtips perhaps for a single pair of shoes.

I hear it's rainy there, and I've always struggled dressing decently in the 30-60F temperature range.
 

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Any tips?

There is a wedding as well, and I'd like to do minimal packing. All I know is blazer and dressier pressed khakis are going for certain. Medium brown wingtips perhaps for a single pair of shoes.

I hear it's rainy there, and I've always struggled dressing decently in the 30-60F temperature range.
One thing I do suggest is that your single pair of shoes have a rubber sole. I have a pair of black wingtips with a storm welt and rubber soles that is useful for travel in inclement weather. Not my most beautiful shoes but sometimes function over beauty. If you have a trench coat it's nice if it has a removable lining so if it gets too hot you have some versatility. The umbrella is not as important if you are staying at a hotel since they often will have umbrellas. Other than that I try to stay with one color scheme when packing light so if you are wearing brown shoes and khakis then for example just stick with tan pants for your second pair, etc..
 
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