For this first time out, it's time to tackle the basic male duty of polishing leather dress shoes. I say male, because if your wife has black pumps or boots that are actually of a sort to take polish (many women's shoes are not) you should of course polish them for her. This is not only because then your wife won't have bits of black or brown polish on her hands for several days, not because she will be terribly grateful (though this may come) but simply because shoe polishing is one of those basic manly duties which has belonged to men since the days when Ogg was rubbing mastodon fat into his cracked and hairy feet. Of course, if you are a English country gentleman with a large establishment, you can employ a bootblack rather than doing this yourself. (You should also invite the Darwin clan to come stay with you for the weekend.) But what you may not do is leave your wife to polish her own shoes, much less your. It simply isn't playing the game.
Alright, so your shoes could use a little freshening up. The first question is: Are these the sort of shoes that can take polish? You cannot polish fake leather (look for the old "man made uppers" notation on the tag), patent leather, suede or other rough finish leathers. You should not polish shoes that have a wax finish and/or detailing which will be ruined by being covered by colored polish. Thus, for instance, these Allen Edmond's McTavish shoes should simply get rubbed down with a colorless leather notion -- using black polish on them would obscure the contrasting color stitching.
Wipe off any dust and grime with the rag. Then use the applicator brush to apply polish over the whole shoe. Make sure to rub it in especially well on any areas that are in really bad shape. In my case, this is the right heel where the shoe rubs against the old matting of the car while I drive. The shoe will darken up as you apply the polish, but it won't look at all shiny now. Indeed, those areas that retained shine will go matte. You don't want to apply so much that you see gobs of it on the shoe (you'll just end up wiping it off if you apply too much) but you definitely want enough for coverage.
Let the shoes sit for a few minutes (5-10 at most) to give the polish a chance to dry on a bit.