Choosing the Right Shoes

Put your Best Foot Forward

Steve R. writes: While I like my shoes and have several pair, I am sometimes unsure what style to wear with certain types of clothing and what color will look the best. Can you give me some general advice on what goes with what?

TomTalks: Shoes can make or break an outfit. Shoes are the foundation. Second only to your overall look (and perhaps grooming), the shoes you wear get the most attention and can significantly impact the first impression that others form. Developing a good shoe wardrobe and knowing how to wear each style and color will go a long way toward defining your style.


The Starting Five

As every sports team is comprised of first string players and those who back them up, your shoe wardrobe should have a minimum of a starting five in the rotation (not including your tennis or other athletic shoes, sandals, etc.) What styles best constitute your starting five will depend on the typical formality or your day-to-day dress and your personal style. The five above, all from Allen Edmonds, include Park Avenue, Delray, Hillsborough, Wilbert, & Route 100.

To keep it simple, one pair should be clearly formal and dressy, a shoe to wear with a dark suit. Another pair should be obviously casual – to wear with jeans or khakis, but never with a dress pant. The other three should be somewhere in the middle.

What you add to your rotation beyond the starting five should provide more options and depth to complement how you dress most often. If you are among the more sartorial crowd who still wear a suit most days, then you will want at least two or three more pair of formal dress shoes. Whatever the case, the goal is to develop enough rotation and variety that no matter what you choose to wear, your footwear is a perfect complement.

Above is another group of five with a stronger emphasis toward the casual, including Fifth Avenue, Norwich, Big Sur, Katmai, & Sanibel.

Color Coordination

You may have noticed that Brown shoes of varying shades have moved their way to a more prominent place in footwear fashion during the recent decade or so. Very simply, brown goes with everything (except perhaps black.) Dark brown is an ideal complement to a navy suit while a medium brown – walnut, bourbon, chili, etc. – works especially well with medium blue, shades of gray, and all earth tones.


A staple color in the 80’s, Burgundy (Bordeaux) is another way to augment your color options. Many experts would argue that shoes in this color range are the most versatile. The burgundy penny loafer (Walden) and the classic dress slip on (Presidio and Randolph) are the most essential styles.

Following the principles outlined above should help you to develop a shoe rotation that will allow you to put your best foot forward with any look and any occasion.

Stylish from head to toe (or at least at the feet),

tom@tomjames.com

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