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What to wear? Help, please!

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I am a teenage guy visiting Scotland this October...I want to look classy, but not over-the-top. I want to fit in, and not look like a tourist (my greatest phobia). I was thinking khakis, a vest, and a blazer, but I am open to suggestions.

Anyone have any ideas?

Also, which is better. A backpack, or a messenger bag?

Thanks for your help!

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