Back to Basics: Choosing a casual shoe

October 10, 2011 · 70 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 dudes figure out what looks best on them. He also co-founded Fifth&Brannan, a menswear label based in San Francisco. Connect with him on Twitter and Facebook.

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  • http://effortlessgent.com Barron

    I really like both. I think they’re perfect for a super casual summer day, or when at the coast or near a body of water, etc.

    I’m all about bright color, so I def dig those boat shoes. When I say classic design, I’m talking more about the silhouette rather than the colorway. These ones fit the bill.

  • Tomacco
  • Meek

    Yeah I’m with Micky on the Adidas topic. While I (like the both of you) would never wear those particular pair, I would however throw some on if I’m let’s say…running to the store. I think that a big part of being a well dressed man is diversity. Knowing when to wear the Jordans and Nike/Adidas and knowing when to put on a pair of Allen Edmonds is very important. Let’s say your dating a woman and you two go to the movies. I can almost guarantee that you’ll look stupid wearing a tux. That’d be a great time to throw on a pair of jordans, jeans that fit, and a matching shirt or plain white or black t.

  • Grown up

    Meek, the point of this fashion advice is to not look like a child. Throwing on a “pair of Jordans, jeans that fit, and a … plain white or black t”? That’s exactly how I dressed in third grade. Literally. You’re too old for that. Time to dress like an adult.

  • http://twitter.com/IPv6Freely Chris Jones

    Also consider the source. Very outdoorsy. Mountain biking, camping, etc. I would argue that the birkenstocks and socks fall into the “shoes for a specific purpose” category for such things. Go ahead and wear them at the cottage. Just not in everyday life.

  • quietriot

    This is pretty late.. but what color are those Sperrys in the image? I can’t find them…

  • Steve

    hey barron (or anyone with suggestions),
    What if you are looking for something casual with good support. I am a Doc on my feet in the hospital all day and am looking for a sneaker to go with my scrubs but its got to be something where I can be on my feet all day without them killing me (converse wont cut it). Thanks.

  • cdrinark

    This PF Flyer is MUCH more comfortable than Chucks and offers moderate though not exceptional support.
    http://vip.zappos.com/pf-flyers-bob-cousy-all-american-navy
    I have these and love them. Never cared much for Chucks.

    And you might consider a Keen sneaker. Their anatomical foot beds are generally very supportive.
    http://www.keenfootwear.com/us/en/product/shoes/men/blvd/santiago%20lace/gargoyle

    Just my 2 cents.

  • orlando

    lol at converse, only high school kids and poverty brahs wear that, good luck with that

    also they don’t give any height boost like real shoes, which means if you are a manlet, you stay a manlet

  • http://effortlessgent.com Barron

    Where are you from? It probably is relative. Here in the US, it’s a great choice for a classic, casual shoe. And I never recommend shoes for their “height boost”.

  • RK

    I know this is a fairly old post, but just wanted your opinion since I’m looking to pick up another pair of shoes. My typical daily outfit is usually a pair of chinos (sometimes jeans) and a casual button up shirt. If you had to choose between desert boots and boats shoes, which would you go for?

  • http://effortlessgent.com Barron

    It depends. Where do you live? What’s the weather typically like there? In general if it’s wetter / colder where you are, I’d go with desert boots. I like boat shoes for warmer days, or warmer climes.

  • cdrinark

    I live in the South and have both. I wear my boat shoes almost every day from late spring to early fall, but I wear my Desert Boots almost all year long. So I would probably choose the Desert Boot if I could only have one. Or I might consider something like a Bean Blucher Moc that could go with pants and socks or sockless with shorts.

    Bean Moc

    If you’re looking for TOP QUALITY, I suggest Rancourt and Company for boat shoes or Ranger Mocs. US Made and Awesome! They also have a Blake Chukka that looks like an excellent choice for a Desert Boot.

  • RK

    Thanks for the reply and added suggestions!

  • RK

    I live in the Bay Area too.

    I currently have a pair of navy desert boots, which I really like, but was thinking of picking up a pair of grey ones which I feel would be more versatile. But then that got me thinking, maybe I should pick something else up to diversify.

    BTW… awesome site!

  • http://effortlessgent.com Barron

    Go with one of each! Actually, have you seen the beeswax leather version? I like those a lot: http://www.zappos.com/clarks-desert-boot-beeswax-leather~1

    Also the Oakwood Suede color is a good option.

    Thanks for reading!

  • Ryan

    Any advice on a good desert boot? I’m looking for something in a neutral color… maybe grey? Preferably under $100, too.

  • Sebastian

    Aha I feel outed now, since i’m sometimes that guy wearing his vibrams around town while on very casual outings. They are just so comfy.

  • http://effortlessgent.com Barron

    I know I hate on Vibrams a lot, but they were designed and built for a purpose, and I’m okay with them in the right setting (running, in the gym working out). But when I see guys wearing them on the train, commuting into work, it’s like, cmon.

  • Sebastian

    Aha your points are valid and fair. They are in no way, at all, an even semi formal shoe. They barely wiggle their way past flip-flops on the formality scale. We call them toe-sy shoes cause that’s what they are, silly shoes that feel somehow akin to your ‘cozy’ slippers. I personally just wear mine either a) running, b) when in a park or at the sports/outdoor store c) walmart (I feel if I didn’t wear something weird the crazies might catch on that I shouldn’t actually be there ;) ) and d) to alleviate pain in my bag leg from a rather badass horse-back riding injury.

    So to sum up a rather pointless comment, vibrams are silly, and wonderful and like a hideous Christmas sweater have a time and a place and should be put on display for the world to see, only for the activity it was brought into the world for.

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