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8 Most Comfortable Dress Shoes For Men

Comfortable dress shoes for men that also look good? Yes, please!

Comfortable Dress Shoes

Believe it or not, it is possible to get yourself a pair of comfortable dress shoes. We know, we know, you’re probably thinking that most men’s dress shoes are not comfortable.

But they’re essential to any man’s wardrobe; particularly for those who have to don them most days for work. But when most of us think of ‘comfortable’ dress shoes, we picture hideous shoes that no one under the age of 80 would wear… So, this begs the question: how can I get comfortable dress shoes that look great?

Sole and behold. That’s where we come in.

You need to know what to look for in a shoe that’ll make it comfortable, what leather type is best for your lifestyle (and budget), and you also need to know what brands have mastered how to embed technologies that make dress shoes comfortable in a way that still makes them stylish.

What Makes A Dress Shoe Comfortable?

Think of your favourite pair of running shoes, they’re probably super comfortable, right? You could wear them all day without any issues whatsoever. The most comfortable dress shoes exhibit similar features, which we’ve detailed below:


Feet are designed to move in a very specific way, and what makes most dress shoes so uncomfortable is that they restrict this natural movement. Running shoes better mimic the natural movements of your feet and hence are more comfortable. When looking for comfortable dress shoes, look for pairs with a more flexible upper (the part that covers the top surface of your foot).


Most high-quality dress shoes have a leather sole, which is great for durability but not for comfort, at least to begin with. Running shoes often have a soft foam insole that cushions the foot when it makes contact with the ground and you should look for similar, cushioned insoles in your comfortable dress shoes. Alternatively, if you are willing to wait it out, leather insoles will eventually mould to your foot and become more comfortable than foam alternatives.

Soles & Cushioning

Again reference your running shoes. Their sole is probably made from soft and flexible yet durable foam. Contrast this to your dress shoes which probably have either a leather or hard rubber sole. When you make contact with the ground your running shoe absorbs the impact, whereas your dress shoes don’t, making them more uncomfortable. Whilst you’ll never get the comfort of running shoes in a dress shoe, picking the right type of sole will help make them more wearable.

You should be aware that shoes with Goodyear or Storm welts limit flexibility and are uncomfortable until broken in, which can take a long time. They are more durable than their glued counterparts though so if comfort and flexibility is your priority, go for comfortable dress shoes with a Blake stitch, Bologna stitch or glued sole.

Similarly, consider the stiffness and rigidity of the sole material. Rubber is typically softer and more comfortable whereas leather can be harder and less comfortable. For added comfort, ensure the shoe has some cushioning between the sole and insole.

Leather Types

Leather dress shoes aren’t just leather dress shoes. Those who are serious about how their feet feel need to consider the leather types that comfortable dress shoes are made from and there are four common types to consider.

Full Grain Leather

This is the most common type of leather used and is also the best quality found in comfortable dress shoes. Full-grain leather is characterised by its luxurious and smooth surface with minimal flaws. This means that it’s often used in its natural state without the need for sanding or buffing of imperfections.

More importantly, it’s strong because the fibres and grain haven’t been modified from their natural state. Aesthetically, full-grain also develops a natural patina layer that protects the leather from wear. We still recommend you look after your comfortable dress shoes with additional supplements though.

Top Grain Leather

Top grain leather is the second-highest quality leather found on comfortable dress shoes. It is thinner and therefore more flexible than full-grain leather. Its surface is often sanded and is less breathable. The positive to this is that it has better stain resistance than full-grain leather.

Genuine Leather

If you needed proof that marketing is a powerful tool then this is it. Genuine leather dress shoes are made from leather but they’re the lowest quality you can get. These kinds of shoes are made from the leftover leather of high-end products – the ones that quality shoemakers reject. As a result, these dress shoes are less comfortable on the feet and don’t last as long. Their advantage is that they’re widely available and affordable.

Corrected Grain Leather

One of the lesser-known leathers is the corrected grain. think of this one as a hybrid leather that takes a special type of leather that is further fixed or refined by leatherworkers. What this means is that an artificial grain has been embossed over the top of it before it is refined with sanding, dyes and stains.

It’s also one of the more affordable options for comfortable dress shoes.

Some other helpful DMARGE stories about footwear:

Still a tad confused or overwhelmed? To make this seemingly impossible task of finding comfortable dress shoes easier, we’ve curated a selection of brands that you simply have to check out.

Whether you’re after a wingtip oxford or a cap toe, you’re guaranteed to find the comfortable dress shoe you’ve been looking for with one of the brands featured below.