[Matt S]

Interesting efforts, but I want to say it's trying too hard and not coming up with the best results. When I choose buttons for a jacket, I usually think of how they coordinate with the jacket. In most cases, I try to match my buttons closely to my jackets, so any shirt that is matched to the buttons won't have much contrast with the jacket. I'd mainly just focus on matching brown shoes to the brown leather buttons. If I had metal buttons, I'd match those to other metals.

I wouldn't wear a tie with a chocolate shirt. It's too casual.

 

[Matt S]

Perhaps I could wear it in the current open collar style or under a sweater with the jacket.

The only tie I'm considering is this Metropolitan Museum of Art tie because it is fun and has colors that would be in a couple of ensembles. Its field is black. Either with a black vest or without. A vest may be more formal than the shirt and tie allow.

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I like the idea of a sweater. Burgundy or dark green would be perfect. Otherwise I would just wear the shirt, no tie or waistcoat. The waistcoat and shirt are too close in colour and clash with each other. A burgundy or dark green waistcoat in doeskin or moleskin would go nicely with the jacket, but then you'd need a light-coloured shirt for balance.