Black shoes look great under dark gray wool, but there is a less obvious opportunity to wear them stylishly and that is with dark brown.
Black shoes are not often seen with brown suits of course but that is simply because we do not sight many brown suits in the first place. "No brown in town" is a not unreasonable guideline, however the definition of "town" should really be the center of a major metropolitan area like London where the phrase was coined. Brown's slightly more casual look is perfectly appropriate in small cities and the suburbs, particularly in autumn and winter when it blends in with the colors of the season.
In the top photo, black Cleverley semi-brogues, walnut Bresciani Super 140s Ribbed Wool Hose and a suit in H. Lesser's 11 oz/330 gram dark brown glen check from the Lumb’s Huddersfield Golden Bale book (the trousers normally fall to the shoe but are raised for the photo).
Above the waist, a light blue royal oxford shirt that complements the blue overcheck in the jacket is worn with a navy and silver houndstooth necktie and a silk pocket square printed with a dark red paisley pattern.