Comfortable Dress Shoes

The 10 Most Comfortable Men’s Dress Shoe Brands That Won’t Compromise Your Style

Keep those feet looking sharp without compromise.

Most men’s dress shoes are not comfortable. But they’re essential to any man’s wardrobe; particularly for those men who have to don them most days for work. Obviously, the answer here is to get a pair of dress shoes that are comfortable! But when most of us think of ‘comfortable’ dress shoes though, 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 doesn’t make them un-stylish looking.

What Makes A 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. These are the features your running shoes include that you should be looking for in a comfortable pair of dress shoes.


Believe it or not, feet weren’t designed to be in shoes. In fact, we really shouldn’t be wearing them but society says otherwise. Feet are designed to move in a very specific way, what makes most dress shoes so uncomfortable is that they restrict this natural movement and try to impose a different movement onto your foot. Running shoes better mimic the natural movements of your feet and hence are more comfortable. In order to be more comfortable, look for dress shoes 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 is not comfortable, 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 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 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 they’re 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 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 dress shoes with additional supplements though.

Top Grain Leather

Top grain leather is the second-highest quality leather found on 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 in leather dress shoes.

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Still a tad confused or overwhelmed? To make this seemingly impossible task of finding a leather dress shoe easier, we’ve curated a selection of brands that make dress shoes that both look the part and are ultra-comfortable. Whether you’re after a wingtip oxford or a cap toe, you’re guaranteed to find the dress shoe you’ve been looking for (that’ll also keep you comfy) with one of the brands featured below.

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