12 Rules for Wearing & Caring For Your Dress Shoes

FOLLOW THESE 12 RULES FOR CLASSIC, EASY STYLE

1. Purchase a nice, expensive pair, with genuine leather uppers, a leather welt, and thick leather sole. Care for these properly and they'll last you 10 years or more.
2. With a suit, oxfords or brogues are classic.
3. Slip-on's are okay if they have a high enough vamp (the part of the shoe where the laces are, if they had laces).
4. Shoes with buckles are acceptable if they are to one side.
5. Shoes with tassels are never okay. To quote from a favorite source, "There is no occasion or outfit in civilized society which justifies the wearing of loafers with a leather fringe and a dangling tassel over the vamp. These shoes are an abomination."
6. Ankle boots are daring. They can make a suit look fantastic, if a bit romantic. They are acceptable with a suit if simple in design, however they may not be appropriate for some settings (i.e. The Boardroom)
   
7. With a suit, your shoes should NOT have metal grommets reinforcing the eyelets for the shoelaces. This look is okay with chinos and a blazer, but never a suit.
8. A gentleman knows his laces should be neatly parallel, not in the criss-cross pattern with which you lace your tennis shoes.
9. Black shoes are classic. Long ago many believed only black shoes should be worn with a suit. These rules no longer apply. Brown shoes are very appropriate, although never with a black suit. For more tips on color, see this post.
10. Your shoes and belt should match. However, if you're wearing a suit jacket a belt isn't required. See this post for additional insight on this look.
    
11. Have a cobbler install a thin protective rubber sole for $20. When it wears out, have a new one installed. Spend $20 instead of $200.
12. Most importantly, nothing helps a nice pair of shoes last longer than a regular shine. The good old fashioned way. Read here to see how to properly care for your shoes. And here to read about polishing your shoes.