The Official Owen Edward Guide to Buying Dress Shoes

If you search for “what dress shoes to buy”, Google will serve you up a ton of different blogs that either: 

  1. Give loads of detail but not a lot of practical advice, or
  2. Just tell you to buy literally 10 different pairs (pump the brakes Esquire)

So here's ours: a (legitimately practical) guide to buying dress shoes. 

Lesson 1: Dress Shoes Should FIT Very Tight at First

If you buy a $200 suit and spend $100 on tailoring, you’ll look better every day of the week than someone in a $1,500 suit that doesn’t fit them. The same goes for dress shoes.

DO: Get shoes that feel tight (in terms of width) when you first buy them. They’ll stretch to the shape of your foot. 

DON'T: Get shoes that are comfortable immediately. They’re too big. 

DON'T: Get shoes that are too small lengthwise. Shoes will not get longer.

WHY IT MATTERS: much like your face, shoes get wrinkles. What you want is one or two large creases. What you don’t want is 5-10 small crinkles. Crinkling happens when there’s too much space around your foot. Get tight shoes, and expect them to be uncomfortable for a week (they’ll loosen up).

Lesson 2: Never Buy Rubber-Soled Shoes

Lots of guys advocate having “shitty rain shoes” to whip out when the weather is bad. Which is sweet, if you live in California and basically never need to wear them (like we do). But not so sweet if you live in New York (where it rains 25% of the year), London (30%) or, god help you, Brussels (54%).

WHY IT MATTERS: Rubber doesn’t breathe, so your feet get sweaty (bad), the salt and moisture from your sweat makes the shoes deteriorate (also bad) and, pretty soon, you need new shoes (worse). 

DO : Buy leather-soled shoes, and get a thin rubber tread put on the front; waterproof in many situations, but still somewhat breathable (unlike full rubber soles)

DO: Buy leather-soled shoes, and also buy rubber overshoes (e.g. these Swims) for rainy days

DON'T: Buy rubber-soled shoes. They don’t even really work: if it’s raining or snowing heavily, you’re still going to get wet through the top of your shoes (even if the sole is waterproof)

Lesson 3: Get a Reinforced Toe Box

A reinforced toe box is simply an extra layer of leather in the toe. Without it, your shoes will eventually cave in at the front. In the photo below, the left is a 5 year old pair from Bally. The right is a 2 year old pair from a brand I’ll call “Bed Taker.” See the problem?

DO : Buy shoes with a reinforced toe box

DON'T: Buy shoes without a reinforced toe box. Also, don’t confuse a cap toe with a reinforced toe (you can have one without the other)

HOW TO TELL THE DIFFERENCE: if you’re in-store, give them a feel – it’ll be very obvious whether or not the toe box is reinforced. If you’re online, hope for the best (for the record: Owen Edwards are all reinforced).

Lesson 4: Get A Stacked Leather Heel

Dress shoes come either with a stacked heel, made up of several layers of leather, or a wooden/composite heel, made up of a single solid heel piece. 


  1. If you wear through the heeltip (which is usually rubber), a stacked leather heel can be repaired layer by layer, which is much easier, and cheaper, than replacing an entire heel if you wear through to the wood. 
  2. How to put this? Solid heels make… a lot of noise. Heel noise. You sound like you’re wearing heels. Women’s heels. 

      DO : Get shoes where the heel is constructed from stacked leather

      DON'T: Get shoes where the heel is a single wooden/composite piece

      HOW TO TELL THE DIFFERENCE: look closely at the heel from the side or back. If it’s clearly constructed from several layers (evidenced by horizontal lines, or just being really obvious like in the photo of The Owen below) then you’re good. Otherwise no bueno.

      Lesson 5: Full. Grain. Calfskin.

      Yes, leather is important. I can hear you saying “no shit” through the screen. And there are tons of guides explaining the types: try this one or this one. Here’s the punchline: you want full-grain calfskin. What you might not know is how to identify it.

      WHY IT MATTERS: full-grain is the closest to real skin, which means it’s the most flexible (good), breathable (good) and durable (also good). 

      HOW TO TELL THE DIFFERENCE: Well, first of all, brands that use full-grain calfskin will usually just straight up tell you (like we do). If they don’t, you need to look at skin pores. Calfskin has a very fine (i.e. dense) grain, and full-grain means the outermost layer of skin, so it comes with surface imperfections. Good brands will cut around those scratches and marks, but when you look closely, you should see a dense pattern of very small pores, with natural variations in their size and spacing. Just like in this photo of our shoes (zoomed, showing ~1x3 inches of leather): 

      Leather that looks too perfect is probably not full-grain. It will either be perfectly smooth (because the imperfections have been sanded down), or perfectly "skin-like" (because it’s been sanded down, and then stamped with a fake, perfectly consistent skin pattern).

      Lesson 6: WEAR OWEN EDWARD

      We make simple, very high quality dress shoes in Italy. Get some.

      DO : Wear Owen Edward.

      1 comment

      • Erik M. Steadman

        What d I do ,with a 3E width , I am usually an 11 1/2 , what size would be best; don’t quote me but the last pair of dress shoes were that size !!!

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