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.

PUBLISHED October 10, 2011


Barron is the Founding Editor of Effortless Gent and the Cladright Association. He's from San Francisco but currently living in New York. Connect with him on Twitter, Facebook, Instagram, or Tumblr.



  • 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://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.

    • Anonymous

      I call that look the Larry David.

  • 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://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://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). :)

  • 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.

    • 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.

  • 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).

      • 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.

  • Kennnedy

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

    • http://effortlessgent.com Barron

      Sure!

  • 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

      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!

      • 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.

  • 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.

    • 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.

  • 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.

  • 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!

    • 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
  • 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.

  • 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.

      • 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!

    • 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!

  • 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.

        • http://www.google.com/profiles/paulabrahamsmusic Paul Abrahams

          I see young ladies here all the time wearing running shoes to work. They slip on the heels once they arrive. :)

  • Brian

    Hey Barron,
    I’m looking to pick up some chukkas or desert boots. I really like the Red Wing 9017s and the Vintage Vaughn – both seem to be great construction, look durable, and have the pretty much the exact style I want in a chukka. BUT – I’m 22 and finishing school, and am not sure I’m ready to drop $300 on some everyday chukkas. I found another pair that I’ve been eyeing for a long time from the UK – Frank Wright Smiths. They’re discontinued but I found some I can snag for about $100.. thoughts?

    The smiths are full leather upper with a synthetic sole, and have a nice construction, but look thin. Any thoughts are appreciated — thanks!

  • code

    In aus wearing flip flops (thongs) is the norm