I’m generally fashion indifferent and have got along fine, but for our trip to Hawaii my wife bought a fair amount of new dresses that were frankly incredible. The only issue is my very basic attire did not match the level she was bringing and she deserved someone much more put together next to her.

I’d like to see those clothes again and I’ve been thinking through the kinds of dates that they would be ideal for, but I also need to be better. I’m looking for clothes for maybe two nights out (hopefully interchangeable items) that work for a guy who sweats easily and would likely be spending at least some time outside in heat and humidity.

I realize this can be a bit vague, so I’m happy to answer any questions, but I have no idea of where to start, so I don’t know what kind of basic info I should provide.

Thanks for any help!