I think the key is to accessorize and/or add color if possible whenever wearing black
Related: Trust Me, I Know Good Shoes, and These Party-Ready Pairs Are Everything How chic is this, please
(Just note: Some of the brands below use letter sizing, with a range from 1X to 6X.) To figure out which size is best for you, take note from Virginia Sole-Smith, author of the Burnt Toast newsletter, who told me that to get the best fit, you should know the measurements of your hips, waist, and inseam, and pay close attention to each brands size charts, rather than committing to a specific number you think you are
While dress shoes are never a miss, consider subbing in a pair of chukkas or wingtips