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Shoes – Men’s Buying Guide


Check out this guide for buying men’s shoes to learn about various men’s shoe styles and understand the difference between US, European and Japanese shoe sizes. We’ve also provided some basic information on the anatomy of a shoe and useful shoe fashion and maintenance tips.

Shoes – parts and construction…

Parts of a shoe

1. Upper : The material on the entire part of the shoe that covers the foot.

2. Lining : The inside portion of the upper that improves comfort and helps increase the shoe’s lifespan.

3. Welt : A strip of material joining the upper to the sole.

4. Outsole : The sole’s exposed part that makes contact with the ground.

5. Insole : The material inside the shoe that creates a layer between the sole and the wearer’s foot.

6. Midsole : The section between the insole and outsole


1. Goodyear Welt

  • Durable, labor-intensive construction by machine or hand.
  • Two-levels of stitching provide more support and water-resistance while also making it very easy to resole the shoe.
  • More expensive.

2. Cemented

  • A quick and cost-effective method of attaching the sole of a shoe.
  • Soles are attached with adhesives and without any welting.
  • Ideal for chukka boots, sneakers and shoes with rubber soles.
  • Resoling not possible

3. Blake Stitch

  • Stitching is done on the inside of the shoe, with the upper wrapped around the insole and secured between it and the outsole.
  • Less expensive.
  • Less water-resistant.
  • Some may find the interior stitching a bit uncomfortable on their feet.

Take your pick of the available styles…

Men’s shoes can be broadly categorized into the following styles based on appearance, construction and purpose/image. Further to this, the color and design can vary based on designers’ vision.

1. Oxfords

The classic style for the modern gentleman, Oxfords are as formal as men’s shoes can get. Also called Balmorals, they can be plain with a toe cap or incorporate embellishments such as perforations or Broguing, which refers to the distinctive decorative perforations on wingtip, semi, quarter and longwing toe cap styles. Oxfords end below the ankle. The base of the laces are stitched to the top of the shoes for a more formal and elegant look. That’s why they make good dress shoes for weddings, religious ceremonies and corporate events. Oxfords are also a popular choice in office wear.

2. Derbys

At first glance, Derby men’s shoes may look like Oxfords. But their laces are open at the bottom edge, allowing you to release the shoes wider to wear them easily. Like Oxfords, they can be plain or include detailing or perforations on the toe cap. Derby shoes have a less formal image compared to Oxfords. You can pair them just as well with jeans and chinos as with formal pants.

3. Brogue

The easiest way to identify a brogue is to look for perforations more prominently incorporated on the upper part of the shoes. The holes punched into the leather were initially intended to drain water seeping into the shoes. But that was back in the days when brogues were worn on countryside jaunts; today, they’re reserved for city trips in both formal and informal settings.

The four most common patterns on brogue men’s shoes are: wingtip, a ‘W’ shaped design on the toe cap; semi-brogue marked by perforations on the toe cap, some decorative elements on the center and continuing on the edge of the cap; quarter brogues have perforations on the cap toe and serrations along the cap’s edge, without any toe cap perforations or decorative elements; and longwing brogues characterized by a pointed toe cap and a wing design extending to the full length of the shoe and meeting at the heel’s center seam.

4. Chelsea boots

With their origins dating back to the Victorian era when similar boots were worn for horseback riding, Chelsea boots today complement trousers, jeans and skinny suits. These ankle boots have elastic gussets that sit over the ankles and run to the upper part of boots. The elastic panels make it a breeze to slip in and out of the boots while ensuring a snug fit.

5. Loafers

Also called slip-ons, loafers are shoes that do not incorporate any lacing or fastening mechanism; you simply slip into them. Inspired by the moccasins worn by Native Americans, loafers have undergone style transformations over the years, with penny loafers, moc loafers and kiltie loafers being notable styles. Men’s slip-on shoes have low or flat heels.

6. Trainers or Sneakers

These type of footwear are called trainers in the United Kingdom and sneakers in the United States of America. These are traditionally athletic shoes but trainers are now very commonly worn casually for everyday activities. They come in very exciting colours. They also come in a variety of designs and styles. They are worn with laces. The soles are made out of flexible rubber while the top is usually made from canvass or leather.

7. Moccasins

Like loafers, moccasins are slip-on shoes but incorporate laces not used for tying, rather serving a purely decorative purpose. They are made of deerskin or any other soft leather, with the sole and sides carved from one piece of leather.

8. Espadrilles

These flat casual shoes are characterized by their rope soles made from jute rope and a cotton fabric or canvas upper. Originally made in the Pyrenees Mountains, espadrilles amassed popularity in the mid 20th century after such famous personalities as John F Kennedy, Grace Kelly, Pablo Picasso and Ernest Hemingway were seen wearing them.

9. Chukka boots

Chukka boots are ankle-length boots made from suede or calfskin, and incorporating two or three pairs of eyelets. Their openings fit less snugly and more loosely on the ankles.

10. Boat shoes

As their name implies, boat or deck shoes are intended to be used on a boat. They are crafted from leather or canvas with rubber soles that don’t leave marks on the deck. The soles have a siping pattern to offer grip on a wet deck while leather construction is meant to provide water resistance. While originally intended to deliver functional benefits, boat/deck shoes are today worn to make a style statement.

Fashion and care tips…

  • Invest in a couple of pairs of sensible and stylish shoes for formal, semi-formal and casual occasions. Maintain at least two pairs each of black and brown Oxfords or Derby shoes that you can wear to work and parties.
  • Match the color of your belt with your shoes. Even better if the finish of the belt and shoes match.
  • A golden rule on complementing suits with footwear is to wear a pair that’s as dark as the suit. Light colored shoes, say brown, with a dark suit, say black, have a jarring effect.
  • Socks with sandals are a strict no-no unless you want to stand out for all the wrong reasons!
  • Before stepping out in your new leather shoes, apply a coat of water repellant to the leather to seal it and allow the moisture to escape. This is because moisture can cause the leather to stretch or shrink, and affect its original fit and look.
  • Nourish and moisturize your dress shoes with shoe polish every day.
  • Use shoe trees to prevent leather from shrinking and help it retain its form
  • Soles take a beating; replace them when they start feeling uncomfortable and looking worn-out.

Size chart…

Sizing chart
UK 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 12.0
EU 39.0 39.5 40.0 40.5 41.0 41.5 42.0 42.5 43.0 43.5 44.0 44.5 45.0 45.5 46.0
US/CAN 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 12.0 12.5 13.0
Japan 24.0 24.5 25.0 25.5 26.0 26.5 27.0 27.5 28.0 28.5 29.0 29.5 30.0 30.5 31.0
Timberland sizing chart
UK 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 12.0
EU 38 39 39.5 40 41 41.5 42 43 43.5 44 44.5 45 45.5 46 47
US/Can 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 12.0 12.5
Japan 24 24 24.5 25 25.5 26 26.5 27 27 27.5 28 28.5 29 29.5 30