Jeans and Footwear: How to Choose the Right Shoes

Once upon a time, jeans were the most casual of casual clothing. If you wanted to put together an outfit that was simple and nonchalant, you put anything on with a pair of jeans.

Today, jeans fashion is much more complex. By no means are jeans considered formalwear, but jeans do tend to indicate a more intentional outfit than most casualwear, like joggers and sweatpants. Thus, you need to be more purposeful with the other elements of your outfit when you plan to wear jeans, especially when it comes to your footwear.

Fortunately, you don’t need to learn through trial and error. This guide will help you understand the rules and regulations for pairing jeans and shoes, so you can feel comfortable and confident in any situation.


Once taboo outside the gym, sneakers have become the quintessential footwear for an outfit with jeans. Casual and comfortable, sneakers come in a variety of colors, shapes, and designs, from simple white or black to big and bold. If the rest of your outfit is relatively plain, you can go wild with your sneaker fashion, wearing the expensive and brightly hued Air Jordans you rarely take out of their box. However, unassuming and plain sneakers are best for smart-casual occasions when you want to look effortlessly chic in your men’s jeans.


Perhaps the first footwear ever worn with jeans, boots remain one of the most stylish footwear options — and they come in an abundance of styles. Generally, you want to opt for boots that can be dressed down to read as casual or smart-casual, like these:

Leather hiking boots. Unlike the performance footwear designed for hiking, plain leather hiking boots are appropriate as footwear off the mountain.

Work boot. Thick-soled and rugged for use on dangerous job sites, these boots can function as eye-catching accessories when paired with plain jeans.

Chelsea boot. Iconic due to an elastic panel along the ankle that makes them the easiest boot to slide on and off, the Chelsea boot is sleek and smart.

Chukka. Also called a desert boot, the chukka is exceedingly versatile, capable of being dressed up or down as you desire.

Derby Shoes

The true origin of Derby shoes is a bit shrouded in mystery, but today this footwear is an essential component of any men’s wardrobe. With open laces, an elongated and rounded toe and three panels stitched together, the Derby has long been the informal cousin of the Oxford. Today, not many men can tell the difference between these two types of shoes, but the Derby remains a safer choice for outfits with jeans — as long as you are dressing up the rest of your outfit. A button-up shirt and/or a sport coat are essential for balancing the stately appearance of the Derby.

Oxford Shoes

Then again, it is possible to wear a formal Oxford shoe with a pair of jeans — as long as you choose the right pair of jeans. Opposed to Derby shoes, Oxfords have closed laces, low heels and as many as four panels stitched to the leather sole. You can find less formal Oxfords, which tend to have eye-catching embellishments like broguing or wingtips, that can be more appropriate for outfits with jeans, and you should try to make them appear even more casual by skipping socks and selecting jeans that show your bare ankle.


Once the utterly unhip footwear of the previous generation, loafers have become a symbol of relaxed luxury, especially when they are dressed down with jeans. Loafers come in many styles, primarily defined by the decoration on their upper: pennies, tassels, horsebits, etc. In truth, boat shoes are a variation of the loafer — but they are best reserved for younger men or men who are actively standing on a boat. Other styles of loafers suit jeans styles well, adding interest and flair to almost any outfit. Polo shirts or turtlenecks layered under smart-casual outwear makes a cohesive and chic ensemble any time of year.

Gone are the days when you could throw on jeans and any old shoes without thinking. Because jeans have become more elevated in the fashion strata, you should try to put together outfits that look and feel fashion-forward — which means selecting the right footwear for the occasion.