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Wearing Dress Shoes With Jeans Can Be Complicated: We're Here To Help

Jeans are one of the most versatile items of clothing in a man’s closet and we know that matching casual men’s shoes with jeans is easy. They always look good with sneakers, driving mocs, and chukka boots, but the dress shoes-jeans relationships is a different story. When wearing dress shoes with jeans, there are some simple rules you should follow.

The featured image is the Kenmoor II Wingtip Oxford in Burgundy.

Rule 1: All jeans are not created equal.

Every pair of jeans is casual, but some more so than others. The key to success is here is matching the jean to the shoe. While even the most casual shoes can go with a pair of dressy jeans, the opposite is not true. Distressed jeans, light wash, or jeans with holes in them do not go well with dress shoes.

Rule 2: Get the right fitting jeans.

If you are wearing dress shoes with jeans you need a modern cut jean. The hem should have a slight break or rest on the top of the shoe, and never drag at the heel. Slim cut jeans with tapered legs look best. Completely rule out any baggy and boot cut jeans.

Rule 3: Be careful with black.

Black is a difficult shoe color to pull off with jeans, especially if the shoe has a bit of shine to it. The only sure thing is to have a black jean. But beware, all black colors are not created equal. If the black color in your pants exactly match your shoes, then you’re in the clear. If it’s the slightest bit off, we’d recommend opting for a different color jean. Cognac or dark brown shoes work much better with jeans, just make sure that there is enough contrast between shoe and jean colors to create depth in your look.

Rule 4: Coordinate the whole.

To pull off the “jean and dress shoe” look, the key is to coordinate everything else you wear. T-shirts and sweatshirts won’t do. To achieve a balanced look, wear a well-fitted button-down dress shirt and top if off with a casual sport coat. And don’t forget to complement the shoes with a perfectly matched belt. Now that you have the rules down, try them with any of these styles, they’re all guaranteed to look great with jeans.

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