Choosing the Right Shoes for Your Outfit

Submitted by SharpMan Editorial Team on Thursday 14th October 2010
In this article
  • Must-have shoes.
  • The "short" story.
  • Perfect pant picks.

Unlike some women (particularly those portrayed on television), most men don’t generally "obsess" about their shoes. Although a shoe obsession is not mandatory for the fashion-savvy, a little thought put into shoe choices is. Read on for the SharpGrooming skinny:

Must-Have Shoes

Here’s a scenario: when looking for a pair of shoes each morning, you have three to choose from, all scattered, muddied and torn, of course: old Nike sneakers, your basic brown Doc Marten open shoes/sandals and the requisite "dress" shoes. The dress shoes, a pair of plain black lace-ups, are splitting at the side. If this accurately describes your bedroom floor, it’s time for more info.

Here’s a breakdown of the basic shoe types every SharpMan should own:

  • one pair of clean, white-based sneakers;
  • one pair of brown or black leather sandals or open-toe shoes;
  • one pair of black dress shoes;
  • optional: one pair of brown dress or "semi-dress" shoes.

If you own these three pairs of shoes, you should be able to correctly coordinate any outfit in your closet. The question is, how do you know which shoe should be paired with which outfit?

The "Short" Story: Matching Your Shoes to Your Shorts

The biggest fashion faux pas committed by men usually occurs while they are wearing shorts. From boots to shoes ‘n’ socks combos, some footwear should not grace a bare leg. Here are some of the basics of footwear and shorts.

Athletic shorts. Athletic shorts, since they’re casual by nature and worn when engaging in a physical activity, require an athletic sneaker. For days when vigorous activity is expected, grab the old sneakers still in your closet. No one will condemn you for covering those in mud. For a more relaxed afternoon of walking or light activity, choose your clean sneakers.

Blue denim shorts. Here’s another opportunity to wear your athletic sneakers. Blue jeans and blue denim shorts are casual by nature, so a casual shoe is your best choice. Sandals or open-toe shoes are another great choice.

Consider your color-mixing choices, here. If you like wearing sandals and also enjoy being more "put together," you may want to consider purchasing both a black and brown pair of sandals. Here are some general guidelines:

  • If your shirt is navy blue or brown, avoid black sandals.
  • Brown is a universal choice, but should be used with caution when pairing with black and grays.

Dress shorts. Depending on the color, a sneaker or sandal is your best choice with dress shorts. Clean, white-based sneakers will work with any color, as long as you’re trying to dress down your outfit for a very casual look. Of course, the event to which you will be wearing the shoes will determine whether your sneakers are appropriate. For example, a stroll through the park is sneaker-appropriate, while a dinner date is not. To dress up your shorts, try a dress (not athletic) sandal. Again, the black and brown color rules apply. Khaki-colored shorts and a black or gray T-shirt should ideally be paired with a black sandal, while any other color shirt will work with a brown sandal.

Shorts-and-shoes don’ts. Avoid boots, loafers or any other footwear besides sneakers and sandals with shorts. Avoid wearing socks with your sandals. Enough said.

Perfect Pant Picks

Lucky for you, pants don’t have as many "rules" as shorts do. But choosing the correct shoes is just as important. Here are some tips:

Athletic pants. Just like athletic shorts, track or wind pants and sweatpants should be paired with an athletic shoe.

Blue jeans. Blue jeans are your most versatile pants for choosing shoes. For a quick run to the grocery store or outdoor activity, athletic shoes are a fine choice. If you want to dress up your jeans, dress shoes or boots are your best bet. As a rule, if you’re wearing a T-shirt or another very casual shirt, choose the sneakers, while a button down or polo shirt should be matched to a more "dressy" shoe.

Cargo pants. Similar to jeans, cargo pants are also a versatile choice. Although they are not as casual as jeans, they suggest a laid-back approach to dressing. Sneakers are fine for a casual look, while dress shoes offer a sophisticated touch.

Classic khakis. Classic khakis call for a classic shoe; that’s why dress shoes work best with this type of pant. Boots, of course, are also acceptable. Although many men regard khakis as "brown" in color, they are actually neutral. So, black or brown shoes work equally well, depending on the color of your shirt.

Trousers. Trousers should be paired with a dress shoe or boot. The most popular trouser colors for men — black and gray — should be matched with black footwear. And, especially as part of a suit, your shoes should be polished and scuff-free.

This article last updated on Thursday 14th October 2010
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