The Guy’s Guide to Shoes


A recent tally has my collection at 33 pairs of in-use shoes, so the question of “how many is too many” has been on my mind lately. With the menswear industry beginning to make strides in the everyday closets of everyday men (attention to fit, better fabrics), there’s still a long way to go when it comes to our shoes.

Nowadays there are footwear options for men of every taste and lifestyle, so sifting through the trends to find the classics can be tough. Here’s a guide to help you navigate the stylish waters:

All-time Top 5 (hypothetically speaking, of course) Desert Island Shoe List

Oxford dress shoe

guyoxfordsThis shoe comes in a variety of statement colours, but timeless black or brown is best. Black is the standard, but brown is a great neutral to wear in transition seasons (spring and fall). I wear brown more and find I get much more use out of them.

Penny Loafer

guypennyloaferTo those unfamiliar with Penny Loafers, they’re the classier cousin of your friend Boat Shoe. Upgrading your footwear to a shoe like this is a super simple way to stand out among the crowd. A couple of years ago I bought my first pair of penny loafers and they quickly became my go-to semi casual shoe. I typically pair them with a light button down, dark slim jeans and no-show socks.

Classic sneakers
guysneakersThese shoes can be dressed up, or dressed down easily. They are comfortable and effortlessly stylish and can range in price point. Vans classics are the standard for me.

Athletic Shoe

guyathleticshoeNormally this type of shoe would not have been on my list, but my girlfriend started making me go on hikes with her and I’ve realized that proper footwear makes a world of difference. The last thing you want to be doing is going on a run in a pair of DC’s (on that note, please never wear DC’s, unless you’re physically ON a skateboard).

Military Style boot

guybootsYou will be happy to have these when the weather gets cold. The thick soles and higher ankle coverage will keep you warm, and you’ll look super badass (double bonus). They obviously aren’t snow boots so refrain from wearing anything leather in sleet or snow (unless properly treated), but they are the perfect for those in-between days.

Feature image sourced on Pinterest. Featured shoes sourced on


4 responses to “The Guy’s Guide to Shoes

  1. Lovely thing about fashion right now is that it’s beautiful to wear runners with outfits including suits or peacoats.

  2. There’s no such thing as too many shoes.
    I’m up to 142 pairs, and yes, they are all worn.
    They’re on a constant rotating roster.

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