Collective Wisdom: Shoes For Business Casual

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Gentlemen, your sage advice is needed for hapless reader Mr. J, who can’t figure out what shoes to wear to work.

He writes:

I need help fast. My new workplace calls for business casual. I really don’t do “casual” in the sense they mean, so I will be wearing a navy blazer, dress slacks, and dress khakis on a normal basis. My issue is shoes. I would normally wear my Alden penny loafers with that dress described above. However, I won’t wear the same shoe everyday. I’m more of a lace-up guy in style to begin with, but I need some help with the type of dress I will be wearing. I prefer Alden, because I have graduated to that after growing up on Allen Edmonds. Is there an Ivy or trad style of laceup that would be appropriate for me in my situation? Thanks from below the Mason-Dixon Line.

For the above image I selected Alden’s split-toe blucher, since he wanted a laceup. However, while I certainly have a personal preference for loafers, I think there’s a bit of logic ingongruity in wearing lace-ups without a tie, as well as being less faithful to Ivy tradition, in which loafers are worn not only with jacket and tie, but also a suit, and in die-hard cases, even a three-piece suit.

Feel free to weigh in with as many ideas as possible until Mr. J is completely overwhelmed with options. — CC

43 Comments on "Collective Wisdom: Shoes For Business Casual"

  1. Cuastic Man | June 11, 2018 at 3:52 pm |

    Longwing brogues are the first thing that comes to mind. They are casual, lace up, and widely available.

  2. I second Cuastic Man; I work in a business casual environment and rotate AE Cavanaugh penny loafers and some very nice but inexpensive LWBs I scored from J. Crew. Any sort of derby would probably do.

  3. My initial instinct would be for longwing brogues as well. I don’t know how casual Mr. J wants to get, but he can also explore throwing in dressier versions of camp-style or blucher-style mocs, which I like to do with my business casual attire in the summertime.

    @CC – On your comment about loafers with suits, I regularly sport a three-piece suit with cordovan tassel loafers. I’ve even gone so far as to wear my BB/Alden black cordovan tassels with black tie (gasp!) on those rare occasions when I’m called to break out the evening wear. I have to say, I like the way it feels, and I will probably continue to sport this look.

  4. Charlottesville | June 11, 2018 at 4:24 pm |

    I like the split-toed blucher Christian suggests, and really should look into adding a pair to my own shoe rack. Like CM, I am also a longwing fan, and Alden makes a beauty in shell cordovan. Alden’s lace-up, plain-toe bluchers are another good option. With the proposed outfit, again following CC’s lead, I would go with tassel loafers as a supplement to the penny loafers. All of these can be had in black, cordovan and shades of brown, which adds to the options. I wish the Bass Sportocasin were still available, but alas it has gone the way of spats and congress gaiters. If you can stand being a bit more casual, canvas Topsiders can be nice with a blazer and cotton pants (perhaps blue oxford cloth or Nantucket reds as a change from khakis), but this may be more casual than you are comfortable with for work. Since I gather that you are a fellow southerner, white bucks and tan bucks are a good option. I too tend to be a suit or sport coat and tie guy in the office, and limit the more casual options (including white bucks and Topsiders) to weekends or perhaps a casual Friday.

  5. Mitchell S. | June 11, 2018 at 4:28 pm |

    @Mr.J: I’m guessing that you want something versatile and comfortable even in hot weather. A pair of lace-ups you can dress up with khakis or dress down with jeans.

    Try Pikolinos, they are a comfortable, business casual brand from Spain. A lot of their shoes are perforated so they let the heat and perspiration out. I hate to sound like an ad (they are not paying me) but they the first shoe that came to mind.

    If that doesn’t suit you, then I recommend some boat shoes. I wear Bass because they can be worn with jeans, khakis and a tie or shorts.

  6. Evan Everhart | June 11, 2018 at 4:30 pm |

    AE or Alden tassel loafers also came to my mind immediately followed by longwing blucher wingtips and then plain toe bluchers as well as the ubiquitous split toe moc lace up bluchers as Christian used for the above article image. Have you considered rotating between English tan, brown, and perhaps burnished chili and or cordovan in 1 to 3 styles? That’s usually my approach, though I reserve any sort of mocassin toed shoes for Thursdays and Fridays with wing tips and cap toes for the rest of the week.

  7. Evan Everhart | June 11, 2018 at 4:34 pm |

    *even in my relatively (see overtly other than myself – casual office)
    Great minds think alike – again! We both thought up those plain toe bluchers. How are you Sir?

  8. Mitchell S. | June 11, 2018 at 4:43 pm |

    @Mr.J: Since you are a Southerner it probably gets hotter than Georgia asphalt in the summer.

    Go for something like Allen Edmonds shoes that feature woven leather that will keep you cool. Also, the brand Geox has perforations in the sole that keep out heat and perspiration. Finally, Ecco is a Danish brand whose shoes are as comfortable as Mephistos but cost much less.

  9. For my generation, the longwing gunboats are THE shoe of business, and they go with virtually anything. With a dark suit for the boardroom look, with Khakis on the weekend and, even though you don’t see it much anymore, they look fine with blue jeans. Presently, I have on a pair of Florsheim Imperials that I’ve had re-soled more times than I can recall. They have a classic everyman image that transcends any loafer, buck or sneaker. A longwing is trusted without being pompous. A can-do shoe for a can-do man.

  10. Johnny Reb | June 11, 2018 at 5:05 pm |

    Alden Tan NST, Alden Tan Wingtip Bal , Alden Burgundy Tassel Loafer, Alden Cordovan Shell 8 Full Strap for casual….don’t even think about black…will look like a funeral home director…Shell 8 or Burgundy passes muster…better know your last & size…if you are gonna roll with Alden’s, better know how to shine em, enuff said

  11. Charlottesville | June 11, 2018 at 5:10 pm |

    Evan – I am well and hope you are the same.

  12. Canadian Trad | June 11, 2018 at 5:25 pm |

    I alternate taupe bucks and oxblood cap toe derbies in my casual office. Daily uniform is a button down and khakis.

  13. Roger Sack | June 11, 2018 at 6:09 pm |

    I like neither longwings nor almost anything from Alden.
    To me Aldens are gratuitously “clunky”. For shoes that
    are quite conservative yet a bit more elegant, I recommend
    Ludwig Reiter. I have several pairs in the three eyelet derby model
    in suede and black water buffalo hide. They have worn as well
    as Aldens. Unfortunately, not easily found in the US.

  14. My go-to “casual” shoes are Johnson & Murphy taupe bucks and penny loafers. My J&M split-toe English Tan lace-ups can dress up my BB khakis or cords, or work with any suit. (I think it’s worth noting that “casual” offers its best with contrast.) My black Aldens are reserved for funerals, and fortunately my last one was in 2011. Of course there are kicks–my choice here is Adidas Stans, but you have to dress up the top half of you a bit more to pull this off in an office setting, IMHO. Someone suggested Sperry boat shoes …. NO! Are you a businessman or a conceited jerk!?!? To augment grunge, I’d suggest a pocket handkerchief to leaven the bread. I work in NYC, so this entire discussion depends severely on industry which you haven’t specified. Ad agency? Dress way, way down for cred. Publishing requires your description above de-escalated several floors below decent clothing (journalists are notoriously scruffy, which you might find politically appealing, Bernie-wise). Financial? Ditch the tie but not much else. I’ve seen two thousand dollar blazers atop torn jeans, which is weird in my opinion but if you can pull it off with a pocket square go for it. Frankly, I long for “the man in the gray flannel suit” period. That would be me, taking all the guesswork out of it. Even Rob Petrie dressed this way and fully enjoyed life with Laura (ah, MTM, you fox you!!)

  15. Any half or full brogues would do perfectly well. Also, blucher style is perhaps more preferable than Oxford for business casual, although, half or full brougues are by definition on the casual side of the dress shoe spectrum, even with the closed lacing. Split toe blucher as pictured at the top of the page is also an excellent option. Horsebit loafers could work great as well, if you’re into that at all.

  16. Jack Gant | June 11, 2018 at 7:06 pm |

    immutable laws:
    NEVER wear pennies with suits; Alden (or comparable) tassels with “country” suits. like tweed or seersucker.
    desrt boots in sane colors work nicely with khaki, as do other suedes.
    thin-soled. nicely leathered loafers of Italian heritage, sockless, with linen but no tie.
    If you’ve got cojones, saddles are a nice comprmise between too dressy and too casual.

  17. Mr.J:
    CC nailed it out of the gate. Get the split toe shoe above…and in that color. Case closed.

  18. @Jack Gant

    I think you mean ovaries.

  19. I’m a lawyer in a small Pennsylvania city where various iterations of business casual are normal, even in law and finance. For my business casual (tweed or blazer-and-khakis) days, I wear either Alden cordovan penny loafers or Alden tan bucks. For suit days, AE McAllisters or Fifth Avenues in either burgundy or black. Topsiders are for days when no clients are coming in or I’m blowing off the afternoon to play golf.

  20. While Mr. J may have “graduated” from AE, I think he’s missing out if he doesn’t consider the Strand. In walnut for his ubiquitous khakis.

    And I prefer the short wing blucher over the LWB.

  21. René Lebenthal | June 12, 2018 at 3:29 am |

    From the French Point of view I could recommend Paraboot shoes, especially the Avignon or the Chambord model. They are extremely comfortable and very versatile and long lasting. And they are lace-ups.

  22. Johnny Rotterdam | June 12, 2018 at 6:28 am |

    I doubt if the Finsbury are actually made in England, Norton. A loafer is ingongruous. Mr. J needs a laceup.

  23. Trad Seeker | June 12, 2018 at 8:11 am |

    Go with the Alden, J. Can’t go wrong and very Trad.

    Btw, can any of the commentariat point me in the right direction of a trad mobile phone that’ll fit nicely in the pocket of my OCBD without pulling the shirt out of shape?

  24. Van Coover | June 12, 2018 at 10:22 am |

    I would certainly give the Finsburgh a shot. Very smart and good value for the hapless.

    The tradliest phone? My vote is iPhone. Won’t mess with the collar role.

  25. Blow their minds with the Paraboot Chambord Café. It’s a workplace winner (even below the Mason-Dixon Line).

  26. Canadian Trad | June 12, 2018 at 12:43 pm |

    @Trad Seeker IPhone SE is a reasonably sized device, a good value for money, and not flashy. I don’t know if I’d ever call a phone Trad, but this ticks some of the Tradly boxes.

  27. whiskeydent | June 12, 2018 at 3:33 pm |

    If he wants to stay with laces, he could consider something like the AE Strand as an alternative to the long or short wings (should they be called no wings?). I’d also look at oxfords in pebble grain or suede because they lend a more casual air to things. He could even consider something more outdoorsy like the AE Wilbert or Badlands. Then there are boot versions of all of these. And then there are the various shades of brown to consider (I just don’t like black shoes for casual). He has a lot more options than he realizes.

  28. Jonathan Sanders | June 12, 2018 at 4:18 pm |

    Think “Suede”. Alden has great unlined loafers in suede. They also have a great plain toe blucher/derby done in the same construction. Also, if you have a little Mod in you, Clarks Desert boots are great too. Given that you’re in the South, wearing fully constructed lace up shoes like traditional Aldens or AE’s feels too much. I’d want some breath-ability and suppleness. Also, a Gucci loafer wouldn’t suck either.

  29. Charlottesville | June 12, 2018 at 5:29 pm |

    I like Whiskeydent’s suggestion of pebble grain. I have a few pairs of pebble-grain longwings in shades of brown, tan and black (wearing the black ones today with a suit). I also tend to agree that black shoes are not great for most casual outfits but if you are wearing gray, tropical-weight wool pants and a blazer or gray sport coat, they can work well. I wore a black-and-white, silk-and-linen POW sport coat from J. Press and charcoal pants with a black knit tie and black loafers yesterday. If you lose the tie, I think that is about as “office casual” as a blazer and khakis, and offers a little variety. Of course, cordovan loafers would also work well.

  30. whiskeydent | June 12, 2018 at 5:52 pm |

    Pebble grains also don’t need frequent shining to look good. Wipe off the dust with damp towel or perhaps one of those quick shine wipes and you’re ready to go.

  31. I work in a business casual environment, which in my case means chinos and button down shirts. I usually alternate between two pairs of suede lace-up bluchers, one in dark brown and the other in navy. I sometimes wear a pair of leather double monks in walnut. That’s all I really need.

  32. EVAN EVERHART | June 14, 2018 at 5:48 pm |

    Amen to the pebble-grain/Scotch-Grain shoes! I’m also surprised that no one has mentioned Meermin Mallorca or however it’s spelled. I’ve got a pair and love them, great bang for your buck and always tons of “County Calf” aka Scotch/Pebble-Grain leather options in all of the classic styles, usually running around $210. USD.

    I think the most versatile shoe around is a pair of English tan Scotch-grain short wing Oxford wingtips, with a chisel toe, of course. I’m still lamenting my old pair of Bally’s in the same configuration that finally grew too tatty despite all of my best efforts, to retain any suitability or any claim at anything but ill-repute….

  33. Luke Wardle | June 17, 2018 at 7:55 pm |

    AE Cody’s will work perfectly

  34. People – here is a fascinating look at AE’s past:

    How many of these styles still exist today?

    I counted two.

    • whiskeydent | July 14, 2018 at 11:34 am |

      I also found two with the same name, but AE still makes a lot of shoes in the catalogue under different names. For example, the Boulevard in the catalogue appears nearly identical to today’s Delray.

      As a size 14B, AE is just about my only choice for dress shoes, and I feel lucky they’re still around. This weekend, they have a sale going on their factory seconds. There are some real bargains available, and I’m tempted to buy something I don’t really need.

  35. @whiskeydent – agreed!
    I went through many of the AE catalogs yesterday from 1955 through today. I noticed, for example that Park Avenue – didn’t reach it’s current design until the early 1980’s. There has been a Park Avenue since the 1950’s, but the design has changed over time. AE is constantly experimenting with new designs – the vast majority of don’t make it beyond one or a few seasons. AE is great at doing “tradition” but doesn’t do well when it attempts “style.” I can’t find the Strand style before the 2010s – perhaps it existed before 1955. The Fifth Avenue remained unchanged since the earliest catalog I looked at – but there were times when it was unavailable like the mid 2000’s. MacNeil has remained available as a branded shoe relatively unchanged since the 1950s to today.

    • whiskeydent | July 14, 2018 at 9:51 pm |

      I agree with your agreed. And neither of us has touched on the array of lasts with their various fits and looks. They might not be up to the level of Alden, but AE serves a great purpose in the marketplace.

      I sometimes wonder if AE has too many options. Still, I’d think they know a bit more about their business than I do. Especially since I’m a few glasses of pinot grigio down. Cheers!

  36. Brian McNeill | July 17, 2018 at 3:52 pm |

    I have a very high arch, so I generally cannot wear Bluchers.

    When I am wearing something other than a suit to the office, I select a moc toe tassel loafer (with or without a kiltie) OR a two-toned saddle shoe.

    Both styles are available from AE and from JM.

  37. I want to agree with CC on the no tie, no laces policy, but I think it’s more important to get the best shoes you can afford, and wear them often. Unfortunately in our increasingly tie-less world, you’re just not going to get good use out of a great pair of shoes following that rule.

    With than being said, I think tan wingtips by Allen Edmonds, Alden, Church’s, Loake etc etc are a great all around shoe and look great with everything from business casual to dark denim. Also, if you would like to save a few dollars, the Brooks Brothers branded Allen Edmonds go on sale every once in a while.

  38. Hi. Why so much tan? A medium or chocolate brown would be more versatile with grays and navies. Similarly mid or chocolate suede in a blucher with rubber soles keep it casual but still thoghtful.

  39. I always buy dark brown shoes after destroying several pairs of beautiful tan shoes. This happens, for example, when meat fat or oil drips on my shoes.

    I’m surprised by how casual the workforce has become – even just in the last five years. What used to be weekend clothing and weekend shoes is now weekday clothing.

    These hybrid sneaker/dress shoes are in vogue (like ColeHaan Zero Grand). I’m trying to decide if I want to give into this trend – I probably will give them a test drive to see how it feels very soon. Going from AE, Alden, Gucci, Ferragamo to Cole Haan Zero Grand doesn’t feel congruent with me – but the world is rapidly changing and I need to keep up.

    I guess when the CEO of MSFT works in a t-shirt and running shoes – that sort of sets the bar.

  40. I recommend Richard longwing brogues, £275 from Trickers Outlet – They are better than Loake’s and much cheaper than Alden’s.

  41. Arthur McLean | March 28, 2021 at 8:27 pm |

    I think Rockport has some good choices. Suggest checking out what your boss and his boss wear. Yes I know this won’t work if we’re talking women here. Basically wear what others are wearing. Black loafers such as Weejuns are almost foolproof. I’ve worn them from jeans to full evening dress and I think they work quite well running the full range of dress wear.

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