What to wear to work: A guide to men's shoes

Since Paul has scathingly warned you boys not to wear square toed shoes to work in his last post here, I thought I'd invite him back and share some tips on how to find a pair of men's shoes for work.

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Just like picking out any piece of clothing, the cut or shape of the item is the key to making it look good.
Let's break it down for shoes.

1. Toe-tally important

The shape of the toe box, the tip of the shoe that houses your toes, generally determines how sleek the shoe is. The following pictures shows how the shape of the toe box, sleekest on the left to normal-est on the right.

Toe boxes don't have to be round. As much as I rant about the "square-toed" shoe, a "chisel-toe" (on the right) can be elegant as well giving the shoe a more European look.

2. Last, but not least

The last of the shoe is the general structural foundation the shoe is built on. Different companies usually offer different lasts for shoes since a last meant for a formal shoe doesn't necessarily work for a casual shoe or boots. Here's a table of lasts from Allen Edmonds just to get an idea of how comprehensive the shape of a shoe can get.

3. Width: Shoes get fat too

Finally, the width of the shoe can affect the shape of the shoe. The pictures below shows the same model of a shoe with different widths. The right is more narrow ("B" sizing "and a little more sleek looking, at the left is "D" average sizing). Most companies tend not to offer width sizing on shoes opting for the usual "D" fit: for example, a size "10" usually means size "10D".  

Sizes usually are portrayed as number and then a letter after it - i.e. "10D" the most common size, shows the length of the foot with the "10" and the width of the foot with the "D"

Some companies like Allen Edmonds specialise in offering different widths as well. It's worth it to go to your local cobbler or foot shop to get your foot re-sized to capture the length and width as it really is more comfortable and better for your feet in the long run.

Building your collection 

If you're just starting out, the classic captoe is the shoe for you. Captoes are just that line you see separating the laces from the toe box. This is your go-to dress shoe for interviews and dates alike. 

In terms of shape, Paul Evans absolutely nails it: the cap-toe placement is perfect and has a sleek, spear-like last. 

Here are my recommendations:

The go-to: Paul Evan's Cagney - $350

Alternatively: Allen Edmond's Park Avenue - $385

Lottery: John Lobb's City II Oxford - $1,265

Starting Out: Jack Erwin's Joe - $195