Back to Basics: Choosing a casual shoe

October 10, 2011 · 75 comments

in Back to Basics, Shoes

I always get questions about what I would consider a good casual, everyday shoe. Hopefully this latest installment of Back to Basics keeps it simple and straight-forward.

I’m answering the question of “What’s a good casual shoe?” based on certain assumptions, so read this carefully before you start defending your precious Crocs.

I’m going to assume you’re engaging in a truly casual activity (getting coffee at Starbucks, shopping for denim, grabbing lunch with the wife or girlfriend, returning library books, beer run).

I’m also going to assume you don’t have a black tie event to attend right after said casual activity, that you’re not doing any strenuous physical activity or playing sports, that you’re not a cook, and that you’re not on a beach vacation.

Back to Basics: Choosing a Casual ShoeLooking for the full-sized version? Click here to download (PDF, 18mb)

For casual activity, choose a shoe in the YES pile at the top. You should also strive to have at least several of these shoes in your closet. From left to right, starting at the top:

  • Chuck Taylor Converse and Jack Purcell Converse (not pictured, but similar: Superga, SeaVees, etc. Converse is by far the most widely available)
  • Sperry Top-Sider (or other boat shoe with similar silhouette)
  • desert boot
  • driving shoes
  • bucks
  • penny loafers
  • brogues

If you’re not a fan of every single style of shoe, that’s fine, just pick a couple you like. I personally wear my Sperrys, desert boots, and Chucks the most often. Loafers, bucks, and brogues can be considered a little snazzier, so if you’re going to a laid-back dinner or meeting with friends, go with something in the second row instead of the first.

The shoes in the NO pile should only be used in the situations they were built for… if at all. For example, if you’re a cook in a busy restaurant, I don’t blame you for wearing clogs (or Crocs, I guess). If you’re playing basketball, Jordans make sense. Running? Sure, throw on some New Balances (or Vibrams, I guess). If you’re heading to a break dancing battle, then strap on your shell toe Adidas.

This is important enough to repeat: Certain shoes are meant for certain activities. Respect that, and don’t be the guy wearing Vibrams to the bar, or the guy walking around the city in flip flops.

Thoughts? Questions? Let’s hear em below.

About

Barron is the founder and editor of Effortless Gent, a site dedicated to helping guys figure out what looks best on them. He's based in San Francisco. Connect with him on Twitter and Facebook.

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