The Playbook For The Modern Man

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

Keep those feet looking sharp without compromise.

Comfortable Men's Dress Shoe Brands

One thing that dress shoes are not, is comfortable. There are a few manufacturers that do offer ‘comfortable’ dress shoes, but they often look hideous. So, this begs the question: how can I get comfortable dress shoes that look great?

Sole and behold.

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, however, is not comfortable 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 a 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 a 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.

To make this seemingly impossible task easier, we have found a selection of dress shoes that not long look the part, but are ultra-comfortable too.

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 its natural state. Aesthetically, full grain also develops a natural patina layer which 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 kind 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 which 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.

There’s no need for confusion. To make this seemingly impossible task of finding a leather dress shoe easier, we’ve curated a selection of dress shoes that look the part and are ultra-comfortable.


To make their dress shoes more comfortable, Rockport uses a cushioned footbed, a lightweight sock absorption system and leather construction.

Rockport Style Purpose 3 Plain Toe
Style Purpose 3 Plain Toe $110 | Shop More From Rockport


Florsheim uses both a rubber sole and cushioned insole to ensure comfort in their Amelio Cap-toe Oxford. These minimalistic features ensure the shoe keeps a sleek, yet sharp appearance.

Florsheim Amelio Cap Toe Oxford
Amelio Cap Toe Oxford $110 | Shop More From Florsheim

Johnston & Murphy

These Cap Toe Oxfords from Johnston and Murphy use a soft calfskin leather in combination with their Optima cushioning system to ensure your foot is comfortable at all times, whilst still looking good.

Johnston & Murphy Melton Classic Dress Cap Toe Oxford
Melton Classic Dress Cap Toe Oxford $179 | Shop More From Johnston & Murphy


To ensure comfort in their Rhodes Derby, Bostonian uses a full leather construction that will become more and more comfortable over time. They have also added their OrthoLite footbed to ensure impacts are softened, making the shoe comfortable, even when walking for sustained periods.

Bostonian Rhodes Plain
Rhodes Plain $230 | Shop More From Bostonian


Made from a soft Italian leather and constructed with a Blake stitch, these Belsire’s ensure your foot is only in contacted with soft and comfortable materials. With age, they will become even more comfortable, making your commute more pleasant.

Belsire Black Ginetto Leather Oxfords
Black Ginetto Leather Oxfords $245 | Shop More From Belsire

Cole Haan

The upper on Cole Haan’s Oxford is constructed from a single piece of soft Italian calf leather. This ensures your foot is only in contact with a soft material, that won’t restrict its natural movement. They also use the copyrighted cushioning technology for added comfort.

Cole Haan American Classic Gramercy Derby Wholecut Dress Oxford
American Classic Gramercy Derby Wholecut Dress Oxford $300 | Shop More From Cole Haan

Allen Edmonds

Whilst Allen Edmonds Fifth Avenue Cap-toe Oxford might appear like an uncomfortable shoe, its use of a cork insole that moulds to your foot for a custom fit and black rubber sole makes it ultra-comfortable.

Allan Edmonds Fifth Avenue Cap-Toe Oxford with Dainite Rubber Sole
Fifth Avenue Cap-Toe Oxford with Dainite Rubber Sole $395 | Shop More From Allen Edmonds


Grenson uses a wedged rubber heel in their Elliot Oxford to ensure the wearer is comfortable at all times. If you walk a lot or travel frequently but need to wear a dress shoe, these could be the perfect option for you.

Grenson Elliot Oxford Shoe
Elliot Oxford Shoe $395 | Shop More From Grenson

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