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.

How to Shine Your Shoes

There are certain things a gentleman should know how to do, and shining your shoes is one of them. After years of experience shining my own shoes, I've come to enjoy it and take pride in it. I've never felt comfortable trusting it to an airport or street shiner. I'm sure they do a fine job, but I've always taken responsibility for my shoe care. It's not a complicated or difficult process, and can be quite satisfying. It's important for shoe maintenance as it polishes, waterproofs and restores the leather. It also keeps them looking nice and clean. Follow these steps for a nice shine:

1. Get your area ready. Shoe polish stains, so make sure you're working someplace where you've laid down some newspaper or something to cover anything you don't want to possibly damage. You should also change your clothes if it's something you'd not like to see stained, just in case. Also, I wear latex gloves so I don't stain my fingers.

2. Get your shine kit ready. I've pieced mine together over time, you can also buy a kit with most or all of what you need included. You'll want to make sure you've got the polish to match the color of your shoes, something to apply the polish (a small round brush works, I often use a cotton round), a horsehair brush, and a soft cloth to buff. You may find other implements effective as well. Make sure you use good quality polish. Use a clear or neutral polish for light colored shoes, and take care not to use the wrong brown on brown leather.

3. Clean the shoes with a cloth to remove any dirt and grime.

4. Apply the polish with your brush (dauber)/cotton round/rag. Apply it uniformly. Leave the shoetrees in and tuck in the laces. You can use a bit of water (several drops at a time) to help it go on evenly and with a bit of moisture. I've used this method in the past when I really want a high shine. Use a circular motion. Don't over-apply as this takes the polish longer to dry and doesn't help anyway.

5. Allow the polish to dry. Should take around 10 minutes.

6. Buff the shoes with a horsehair brush using a fast, sweeping motion.

7. Bring out the shine with a soft cloth, rubbing the leather lightly and quickly.

You're done! The leather should feel a bit slick and smooth, and definitely not tacky.