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://twitter.com/rjack2136 Richard Jackson

    Well said. I see guys all the time at places other than the gym or near a trail wearing workout clothing and shoes. Funny part is that they look as if they haven’t set foot in a gym in years if ever. Guys follow this advice and don’t be THAT guy.

  • http://twitter.com/calebwojcik Caleb Wojcik

    I’ve been rocking these as my casual shoe. I got them for like $7 at DSW, but they work. Are these in the YES or No section?

    http://www.onlineshoes.com/mens-margaritaville-spinnaker-frayed-oxford-p_id241590

  • http://twitter.com/MrGBagga Gautam B

    Largely speaking, I agree. However, I have never ever thought that desert shoes are a good look, despite the scores of blogs telling me otherwise. I just can’t think of when I’d want to wear them & therefore, whenever I see someone who looks great otherwise, desert shoes just completely ruin it for me.

  • http://effortlessgent.com Barron

    That’s all personal preference. I’m sure some folks reading this don’t care for penny loafers, or bucks, or whatever. Precisely why I mentioned that everyone should choose a few they like and stick with those (as long as they’re in the YES group). :)

  • http://effortlessgent.com Barron

    Borderline No, mostly because there’s artificial fraying that you didn’t do yourself, through years of usage and awesome adventures.

    But I give you a pass, because you’re in the middle of an epic round-the-country expedition and a big move to San Diego, and I’m jealous. haha.

  • http://effortlessgent.com Barron

    Yeah, that get-up is pretty much everywhere I look, it’s pretty painful. I guess it’s comfortable, but cmon, men. Put a little effort into your appearance.

  • Joel Williams

    It’s just a coincidence that this came out less then a week after an almost identical list came out on Put This On, right?

  • http://effortlessgent.com Barron

    Yep, considering I don’t visit Put This On nearly as much as I should. Smart guys though, so anyone reading this, go check them out right now: putthison.com

    (I see we pulled some of the same images, too. Seems like we can agree!)

  • http://www.wellnessrenegade.com Doug

    Great visual! 

    But white boat shoes? I might have to see some further pics on real people to be convinced of that one.

  • http://effortlessgent.com Barron

    The white shoes are bucks! A staple for the summer season. http://www.unabashedlyprep.com/site/entry/the-white-buck/

    Speaking of white Sperrys though, I saw a pair last summer, they’re awesome. You’d wear them like you’d wear standard white Chuck Taylors.

  • Patrick

    I see none of the shoes in the yes category are black. Isn’t black suitable as a casual shoe? I dislike brown and other earthy colors, they remind me of things like dust, dirt, mud, mold en autum and such. Not things I like close to me.

  • Anonymous

    I call that look the Larry David.

  • Anonymous

    I disagree on the adidas being in the no pile. While I would never wear THOSE adidas because the design is ugly, the model can be used properly. So can some boutique Nike’s.

    Instead of Jack Purcells and All Stars, which every blog seems to be in love with, I would go with Vans Authentics or a toned down pick from Gravis or General Surplus.

    I love this blog as well as Dappered and Primer, but you guys play it way too safe on shoes.

  • http://effortlessgent.com Barron

    Haha, those ones ARE ugly, you’re right. That shell toe model is kinda clunky. I’ve never seen it work right on a well-dressed dude. I like the Sambas, however. And I’ve seen some nice Vans like you mentioned.

    I’m attempting to keep it simple for readers, and since Chucks are pretty much available anywhere, it’s one less thing for them to think about. You sound like you know what you’re doing in the shoe department though, so the above advice probably won’t apply (or rather, you don’t need it to make the right decisions, whereas some readers need more simplicity).

  • http://effortlessgent.com Barron

    Black can work. I’m just biased towards brown shoes (especially when it comes to the dressier options). To me they’re more visually interesting and are available in a variety of shades. Sounds like you dislike brown for the same reasons I like em.

    Black chuck taylors, black leather boat shoes, black driving shoes, black loafers, they work.

  • Kennnedy

    Can desert boots be worn with shorts or are their tops meant to be covered?

  • http://twitter.com/br4hms Carrie

    “grabbing lunch with the wife or girlfriend” not every dude who is reading this blog is necessarily straight :) a phrase like “significant other” would work just as well and be more gender-neutral. Food for thought!

  • http://effortlessgent.com Barron

    Sure!

  • http://effortlessgent.com Barron

    Hi Carrie, good point. Every reader isn’t necessarily a dude either, which I tend to forget. Thanks for your comment!

  • Me

    I’m not straight either, but you have to learn to not be offended by this. It’s a generalization. Just like when I think of a plumber I’m going to say “him” even though it might be a girl. It doesn’t mean anything and I personally just read over it and don’t even notice.

  • Daniel Mildren

    On the yes pile, I’m looking around for a good casual shoe in the likes of the chucks or something like sambas, but I have a minor problem. Size 13 4e width kill my choices a lot. Is there anything you’d suggest that, you know off the top of your head, come in wide? I’m doing my own research, but I figured it wouldn’t hurt to ask. After all, what’s the harm in getting help being stylish? 
    Thanks.

  • http://effortlessgent.com Barron

    Most companies feature wider / bigger sizes, but you may have to order directly from the company’s site, or from Zappos.

    This charcoal gray Converse, for example, is available up to a size 18: http://www.zappos.com/converse-chuck-taylor-all-star-ox-charcoal

    Where do you normally buy shoes from? I imagine that’s tough, but definitely go online for your shoe purchases. Zappos has a great return and exchange policy too, so you have nothing to worry about.

  • http://www.jackthreads.com/invite/thomasroybal Thomas

    This is an old post but I came here via reddit and I’ve gotta say Birks can be styled up (not to mention extremely comfortable).  They’ve become my go-to shoe over some quoddy’s, NB’s, and Abington’s.  They’re resoleable and made in germany from high quality materials which is a win-win-win for me!  Hopefully this doesn’t come up as spam but here’s the 1st place I’ve seen them worn properly

    http://cork-grips.com/2011/09/13/birks-and-socks/

  • http://effortlessgent.com Barron

    Sorry dude, Birkenstocks, no matter how styled up, will never be okay in my book. They look too much like slippers and conjure up images in my head of the hippies at my alma mater, or Dwight Schrute and the extra pair he keeps in his car for special occasions.

    Now that’s not saying they aren’t comfortable (they look like they are) or that they’ll never become trendy (the guy in your photo you linked to is wearing them with 3sixteen denim, so he must be somewhat stylish), but if you ask me, they’ll just never be in my yes pile.

    Appreciate the differing point of view though, and thanks for your comment.

  • http://www.jackthreads.com/invite/thomasroybal Thomas

    Haha I hear ya, to each his own I suppose.  Happy holidays!

  • Nicklaus

    I find well manufactured white sneakers don’t deserve to be in the NO. Whether it be white Nike AFs or some white Adidas (none rubber toe style), they always look like nice with a pair of chinos, a vneck and cardigan

  • http://effortlessgent.com Barron

    Non-shell toe Adidas aren’t in the No category. I’m thinking more along the lines of ratty old running shoes (meant for running) being worn as casual wear. Or bulky shoes that look like Costco’s Court Classics (http://goo.gl/Rh2ro).

    AFs, while I like them, I wouldn’t say it’s the best choice for a grown man trying to up his style. There are more age-appropriate choices, and I think AFs work well for a certain age group but after like, 25, I think they should be worn less and less.

  • Ronald Paek

    Would you consider Vans to be a good casual shoe choice as well? The toe cap area of converse and jack purcells kind of turn me off.

  • http://effortlessgent.com Barron

    Sure, but it depends on the model. It’s like Adidas. I like the Sambas, but I don’t like the clunky shell toe variety.

    I like the Vans Classic lines, the Canvas and Suede Authentics. I wouldn’t wear many others though.

  • Ronald Paek

    Would converse or vans boat shoes be an okay casual shoe choice as well?

  • http://effortlessgent.com Barron

    Sure, but if you like the boat shoe silhouette, why not just get actual boat shoes?

  • Shahzeeq

    Hey Baron,

    How would you wear your tan brogues? Im sure i keep hearing the cardinal rule of wearing it with light colored trousers e.g.; beige, khaki, light grey. Would you think it will also go well with a brighter shade of navy, not the darker ones, or perhaps even dark blue denim? 

  • http://effortlessgent.com Barron

    I wouldn’t wear them with any pants that are too similar in shade. I’d definitely go w/ navy, dark denim, slate gray, etc. That contrast always looks better.

  • cdrinark

    So what are your thoughts on boat shoes other than the standard style pictured.

    For example, the Sperry Billfish.

    http://www.zappos.com/sperry-top-sider-billfish-3-eye-boat-shoe-dark-tan

  • http://effortlessgent.com Barron

    Nope. That’s like serious dad territory.

    Classic styles > everything else

  • Cstauder

    Is it acceptable to wear any of the shoes in the second row with jeans?

  • http://effortlessgent.com Barron

    I assume you mean the second row in the Yes pile. If so, then hell yeah. Make sure they’re the right pair of denim: http://goo.gl/BkL9N

  • Adrian
  • http://effortlessgent.com Barron

    They’re okay. Me personally, I don’t like the thick sole, reminds me of Vans. I say if you’re going with a boat shoe, do a classic style. If you want sneakers, do sneakers. Hybrids always make me feel meh.

  • Dsale48

    What’s wrong with shell toes?  I regularly wear mine (original style/black stripe) with blue jeans and a white tattersal shirt (button-down collar, long sleeve)… Argyle v-neck on top if it’s chilly. They add some pizzaz to what would otherwise be a fairly preppy/conservative combo, plus they’re comfy.

    Then again, the only Chucks I wear are high-tops, so what do I know?

  • http://effortlessgent.com Barron

    I just think they’re too clunky. I like the sleeker Samba though.

  • http://www.facebook.com/people/Jon-Helmkamp/617257122 Jon Helmkamp

    Hey Barron,

    One thing I struggle with is what shoe to pair with what type of shirt. Since I’m JUST starting to rework my wardrobe, I never know how to pair a type of shoe like this that I’ve never worn. Boat shoes, nice denim, and….? Or if it’s with shorts, really all I can think to pair it with is a polo. 

    Considering the next two pairs of shoes I buy will most likely be a canvas shoe and a boat shoe, can you offer a little help with how to pair them up?

    Thanks for all your help. This blog is fantastic and is giving me some great ideas.
    -Jon

  • http://www.facebook.com/people/Jon-Helmkamp/617257122 Jon Helmkamp

    For instance, I definitely feel like a pair of these are in order. The question, which color to go with, and what to wear with them… 
    http://www.urbanoutfitters.com/urban/catalog/productdetail.jsp?id=19614239&itemdescription=true&navAction=jump&color=041&selectedProductSize=false

  • http://effortlessgent.com Barron

    Treat boat shoes like a pair of canvas sneakers; they go with practically everything. You can wear them with shorts, denim, or chinos. For shirts: sport shirts (button-up shirts), polos, t-shirts, sweaters over any of those three, jackets over any of those three, etc.

    If anything, worry more about color complementing than the actual TYPE of shoe, if that makes sense. Boat shoes are casual and can go with any casual outfit (bonus points if you actually use them while on board a boat).

    Re: shoe color, if you stick with a neutral color (natural leather, tan, gray) you can wear them with all the things I’ve mentioned above as they go with almost anything.

  • http://www.facebook.com/people/Jon-Helmkamp/617257122 Jon Helmkamp

    Thanks for your patience with me! I’m just trying to soak up as much as I can, ya know? It can be tough to make changes to your appearance when finances are in a pinch, which is one reason I’m looking for so much clarification before going and making a purchase. I love the thought of a neutral color with the boat shoes; probably the big thing is a matching belt to go with it to tie everything together, yeah?

    I’ve never even thought of layering a sweater over a polo. I’ll have to do some more homework and look up ideas. I’m definitely a visual person.

    Thanks again Barron, This blog is fantastic. I appreciate all the help.
    -Jon

  • http://effortlessgent.com Barron

    Jon, were you not on the pre-notification list for Graduating Your Style? If not, it’s a manual that I’ll be releasing pretty soon. I believe it will help you get started on the right foot. Stay tuned to EG these next few weeks…

  • http://effortlessgent.com Barron

    Just realized I didn’t actually answer your questions. As long as your belt is in the same general hue as your shoes, that should work… I wouldn’t stress over it too much.

    You never thought of wearing a sweater over a polo? What do you do when it’s chilly but not cold enough to wear a coat?

    Anyway, pick up a copy of GYS when it comes out; I’m certain it will answer like 99.4% of your questions. :)

  • Giantsfan69

    Can you plz give a few suggestions for affordable yet stylish driving shoes?

  • http://effortlessgent.com Barron

    What do you consider affordable? I’d first check somewhere like Zappos.com or Endless.com since they have large selections. Barney’s has a house brand driving shoe for $169. Aldo carries some, I think even H&M carry some (on the very affordable end of the scale). Shoes are one of those things where you get what you pay for, so don’t skimp out too much.

  • Steven Lam

    http://us.asos.com/pgeproduct.aspx?iid=1927871

    Hey Barron, I’d really like your opinion on these plimsolls from Fred Perry. I’ve always stuck to vans for summer footwear and have been looking to switch it up. 
    I’m also interested in these boat shoes: http://www1.macys.com/shop/product/rockport-shoes-coastal-springs-boat-shoes?ID=672856&upc_ID=30277171&Quantity=1&seqNo=1&EXTRA_PARAMETER=BAG
    from Rockport. Far from the classic boat shoe design, I know, but I really like the interior art design as well as the navy/red colorway of the shoe. 

    I’d love to hear your opinions on both!

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