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There are a lot of generalizations when it comes to men and shoes. In writing this guide, the last thing I want to do is stereotype by implying that no men care about shoes - or that all women do. Those suggestions are ludicrous and insulting. I've known guys who have extensive wardrobes of men's shoes and who could match anyone pair for pair. I've also known women who couldn't care less whether or not wedges are "hot" this season.

Gender aside, some view shoes as practical necessities, while others have a shoe obsession. Most people probably land somewhere in between. However, of all the men I have known, many of them were uncomfortable wearing a variety of men's shoe styles. For example, many men I've known who had to wear work-type boots for their jobs also had a tendency to stick with that style of footwear after work hours. Other guys I know avoid certain clothes and events because sneakers would be considered inappropriate for the outfit or occasion.

For the most part, I don't believe this is disdain for other styles of shoes, but more of a lack of confidence when it comes to choosing casual shoes. If this sounds like you or someone you know, then you'll want to keep reading for some general tips on choosing men's shoes.

5 General Rules for Men's Shoes

  1. Try to pick a shoe that matches the color of your pants or is darker. Shoes that are lighter than your pants are visually distracting.
  2. Although it is a safe bet, socks do not need to match your shoes. Instead, think of your socks as you would a tie - an item that can bring the whole outfit together.
  3. If you're wearing a belt, try to match your shoes to it - unless, of course, your belt is some multi-colored striped thing.
  4. Invest in high-quality footwear if you can afford it. Shoes that look like they cost a lot now will actually save you money in the long run because they won't fall apart every few years like inferior footwear.
  5. Always choose good fit and comfort over style. You'll be spending a lot of time wearing your new shoes, so your feet should feel good in them.

Men's Shoes for Jeans

You can wear almost any color or style of shoe with jeans. However, you should avoid very shiny shoes that were obviously intended for dressier outfits.

Boots, lug soles, sneakers, loafers and sandals all work great with jeans, so you may find it helpful to let the style of your shirt guide you. For example, a sporty polo shirt might work with a loafer; T-shirts go well with sneakers or retro-style shoes; flannel and plaid shirts pair with work boots or hiking boots; and long, artsy button-downs work well with sandals or contemporary styles.

Men's Shoes for Casual Pants

Whether you call them Dockers, chino, or khakis, most men have some casual pants in their closet or dresser. There are a variety of loafers, oxfords, boat shoes, saddle shoes and other men's shoes that work well with these pants. Even some canvas shoes and high-tops can be worn with casual pants as long as they are clean and presentable.

Let the ornamentation and style of the shoe guide you towards the look you're trying to achieve. For example, a tassle or a buckle is a little more on the dressy side, while a woven pattern or heavy stitching is a little more on the casual side. Generally speaking, the flashier a shoe is, the more casual it is.

Men's Shoes for Dress Pants

With dress pants, shoot for the same type of shoe that you might wear with a suit. Shinier materials usually indicate a dressier shoe, as do less bulky heels and soles. Choose a shoe that is the same color or darker than your pants, and if wearing a belt, match your shoes to it.

You'll also want to pay attention to the toe. Dress shoe toes come in a variety of shapes, from square toes to narrowly pointed wingtips. If you plan to only have one or two pairs of formal shoes, you should get a semi-rounded toe somewhere in the middle, as this will let you wear them with more outfits.

Color Matching for Men's Shoes

  • Black shoes work well with navy blue, grey or black pants.
  • Brown shoes are best suited to tan, brown, beige, greens and other darker earth tones.
  • Burgundy shoes work well with khaki, lighter browns, blue and grey.
  • Tan shoes look great with lighter earth tones, blue, beige, lighter tan or white.
  • Navy blue shoes pair with grey, beige, brown, white, olive and red.