How to shop for mens shoes?

There are various pitfalls when shopping for men’s leather shoes. The variety of choice can be overwhelming and it can be difficult to pay attention to the things that matter most when it comes to styles, quality and occasion. In this article we’ll offer clarity and guidance.


The simplest way to identify shoes is by their style. Some of the most well known styles are Oxford, Derby, Brogue, Monk, Loafer, Moccasin and Chelsea. We’ll explain the differences between them and highlight some of the key characteristics.

Starting from the most formal style we have Oxfords which can be best identified by their low heel and closed lacing that provides a snug fit close to the foot.

The second most formal are Monk shoes that feature a leather strap that is fastened with a buckle. Monk shoes are similar to Oxfords both in construction and shape but can have either a single strap or two straps, referred to as the Double Monk.

Third are Derby shoes that differ from Oxfords by having an open lacing that allows for a wider fit, making them more versatile and casual. 

There is also a special style, the Brogue, which refers to any dress shoes with a detailed floral stitching pattern on the toe. The most well known patterns are wingtip and cap toe.

On a more casual side we have Loafers which are best described by their slip-on style, lack of laces and an elevated seam running along the toe. Loafers are easy to put on and wear highlighting their place as a classic casual shoe. They can also feature decorations such as a plain strap or a strap with a slit - the penny loafer. Even more casual than Loafers are Moccasins - the ultimate driving shoes. Moccasins are made of soft materials, have less structure with soles and heels made for comfort while driving.


The construction of a shoe determines its shape, comfort and durability for years to come. That’s why it’s important to pay attention to how shoes are made before buying. The most crucial aspects here are the stitching technique and the materials used for the sole.

The sole

Here we have two main options - leather or rubber. 

Leather soles are great for wearing for longer periods and especially indoors as leather offers natural breathability, durability and comfort. However in slippery and wet conditions, leather soles get wet and have less grip - in which case they should be paired with rubber overshoes. 

Rubber soles however are more durable and offer extra grip in wet conditions but in exchange are less breathable. Some shoes come with a sole made from a mix of leather and rubber, offering a good compromise between both.

The stitching

Here we’ll highlight three different construction methods and their pros and cons.

One of the most well known techniques is the Goodyear welt - it features a strip of leather (a welt) that is stitched to the upper and the insole along the boundary of the shoe. The space enclosed by the welt is then filled with a breathable material such as cork. Goodyear-welted shoes are extremely durable and take a while to break in.

Next is the Bologna welt where the upper is folded onto itself and then sewn into a tube before attached onto the sole. In this way, the feet are wrapped in soft leather all around resulting in an extremely comfortable and flexible fit.

Finally we have the Blake stitch where the upper is stitched directly onto the sole without using a welt, resulting in lighter weight and better flexibility. However the absence of a welt can result in less durability.


Shoes can also be categorised by when and where to wear them. Different occasions require different levels of formality and shoes should reflect this.

Arguably the most versatile shoes suitable for pairing with any outfit are Oxfords due to their timeless and minimalistic look. For daily wear, having a selection of Oxfords in multiple colors such as brown, burgundy, navy or green makes it even easier to pair with clothing. In a more formal business setting, black or dark brown are the most appropriate colors together with a dark colored pair of socks. And finally Oxfords with black patent leather are a perfect match for wearing with a tuxedo.

Monk shoes are also very versatile and are suitable for pairing with either a formal suit or for a more casual look with chinos or jeans. In case of a more military feel, try Monk shoes with a double strap.

Derby shoes can be worn in very similar occasions as Oxfords but they are better suited for more casual occasions so best to avoid wearing them with a formal suit. Chinos or jeans are very well suited to match with a pair of Derbys.

Loafers come in many different variations that are suitable for different occasions. As a general rule, it’s best to avoid wearing loafers with a formal suit. Due to their construction and design, loafers are best worn in casual occasions - for a smart-casual look pair them with a shirt and chinos and for a more relaxed look, pair with denim jeans and a polo shirt.
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