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I've tried to pair them with jackets and cardigans, but for whatever reason, I can't get the proportions to line up just right

For black tie optional weddings in colder months or the evening, darker colors are typically the way to go

Money well spent

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If you plan to have leftovers, I recommend storing the salad and dressing separately, tossing as needed before serving

I wore a velvet ball cap instead of a beanie