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May 09, 2021 2 min read

Gone are the days when dress shoes and jeans played antagonistic roles across the formality scale; they can now be paired together in several different varieties of stylish outfits–keeping a few essential criteria in mind.

Think to set. Dressy, professional, or casual. As men, we need to understand that each public situation requires a specific sartorial decision, so let's think about how we make the right decision for ourselves. The elements of your wardrobe should complement one another, even in a dressed-down style. Here are a few primary considerations every man should be considering before pairing his favourite got to jeans with a pair of tailored dress shoes: 

  1. What's the occasion? Is it a dress-up event or is it a casual outing?
  2. Your jeans need to fit properly and the style and wash should complement the occasion.
  3. Is proper jean cuffing —this trendy tweak is easy to pull off—appropriate for the occasion.
  4. How and when to combine your overall look with the right dress shoe.

It’s important to understand what your jean selection conveys about you. Different jean brands use various terms. Here's a list of some standard terms:

  • Slim fit: tapered in the waist, with a low-to-medium rise; this works well for dressier occasions.
  • Classic fit: cut at the natural waist with a straight thigh and leg, practical.
  • Relaxed: are high rise, providing room in the thigh and crotch, offers more flexibility, athletic.
  • Loose-fit: sit low on the waist and are baggy throughout the seat and thighs.
  • Skinny leg: are lower rise, slim thigh and leg—best for guys with svelte gams.
  • Straight leg: the jeans are straight through the hip, thigh and leg.
  • Bootcut: are wide-legged, fitting snugly over your boots.

 A semi-formal outfit is appropriate for everyday situations, from the informal office environment to casual dining and entertainment. In order to enhance your appearance with jeans creating a specific look and feel, consider wearing a collared shirt and pullover with loafers, boat shoes or low-top desert boots. For those dressier occasions, feel free to leave your shirt untucked to give you an edge.

Unsure of how to style yourself when wearing dress shoes and jeans properly? Have fun when pairing your jeans and shoes towards creating your personal identities. These types of pairings allow you to discover what works for you while maintaining your personality and your sense of personal sensibility. However, a sloppy pairing of any dress shoes with any jeans, you might happen to have just sitting around. So, there are a few key aspects to ensuring that you achieve the result you are looking for, clean-cut and effortless. The goal is to ensure that the colors of the shoes and the jeans don't diminish from the rest of your outfit and help make a subtle bespoke statement. We want to make sure that the color of both the dress shoes and the jeans you chose complement one another, so it's nice to select a versatile color palette when considering your dress shoe selection and neutral or dark jeans. 

A few dress shoe considerations

For a seriously stylish look, try wearing your jeans with a complimentary pair of monk straps, loafers, brogues, derbies or traditional desert boots.