We all have been in dire situations where we don’t have the right pair of shoes to complete our outfit. And funny enough, we have all been maintaining a shoe collection ever since we got that gum stuck on our economical high school shoes. So, what are we doing wrong?

If eyes are the windows to our soul, I bet shoes are the doors to our style. No matter what job or style you have, we all need to wear shoes (unless you are the missing family of the Flintstones). Collectively, a reasonable 6 – 8 pairs of shoes in your armory is the best number to get yourself started. Organization is key. Your shoe armory should reflect your lifestyle, as it should your wardrobe. Structuring your shoe arsenal in categories is not only efficient but also helps you avoid any shoe dilemma ever again. Let’s get on to it.


  1. The Basics (50%)
  • Invest in two or more  as the name suggests, these represent your everyday footwear. The Oxford work shoes, Penny or tasseled loafers, sneakers, etc. Whatever job or style you have, shoes in this classification will get worn out first. So, investing at least two pairs of work shoes is sensible in sustaining your basics.
  • Be kind to your feet. Make sure comfort tops your list when deciding on a pair of work shoes. You will be wearing them almost everyday, so being able to walk in them and wiggle your toes around is definitely mandatory. Nothing could be worse than having corns, callouses and a pool of blood inside a shoe.

Oxford Shoes Mr. Porter

Penny Loafers Officiene Creative

Common Projects Sneakers


  1. Beyond the Basics (40%)
  • Weekend Warriors – these are your weekend shoes and non-work related event pieces. Be it a golfing tournament, Sunday brunch at The Ritz or jamming with your friends at the new hip club (minus the puke), this is where you put them all.
  • Modern Classics – Nothing could be better than a marriage of classic and modern, just like sushi and foie gras. Consider the brogue with an Espadrille sole perhaps? Horse-bit loafers with Bamboo detailing? These are classic staples with modern finishes that can stand the test of time.

Gucci Bamboo Loafers

Paul Smith Suede Brogues

  1. Collector Items (10%)
  • Investment Pieces – these are your one-of-a-kind items that are so valuable, they might still be in the box. You have invested a lot in them and a mere scratch would bring you to tears. Velvet Tux Slippers from Stobbs and Wootton, priceless Berluti’s, vintage Salvatore Ferragamo or G. J. Cleverly bespoke shoes – these limited edition items are like timepieces that rack up value over the years. Just make sure you invest in classic pieces that will never go out of style.
  • Flaunt it– you will only have a few chances to wear them so flaunt it whenever you can. If you can wear it on a weekend, why not? The point is to enjoy them until they last.  These boots are made for walkin’ right?


Finally, it is crucial that you rotate your basics and never wear the same shoe consecutively. This is to keep the shoe in good shape and order. Variation will make it seem that you have a hundred pairs of shoes when in fact, you only have eight. A good mix of trendy and classic staples will always make you the well-dressed man. Don’t forget to maintain your shoes. Clean, buff, shine or re–sole them, whatever it takes to make sure they are in good condition. Use shoetrees – cedar, please. Using natural shoetrees like cedar will not only keep your shoe silhouette in order, it can also absorb moisture and deodorize it. Trust me, this can make your shoes last for years to come. And lastly, invest in quality-made shoes that not only fit but also make you feel sexy. In this way, you don’t just “walk the walk” but you stride in confidence.

Raffia Black

Berluti One Piece

*Images taken from mrporteronline, gucci, berluti, stobbsandwootton