Right Or Wrong? Three-Piece Suit With Loafers


In our last post we discussed Japan and the concept of menswear rules. Let’s pick up where we left off.

Now I may have been a bit quick on the draw in the previous post, going off on a tirade about close-minded clothes-minded guys obsessed with dressing according to rules and formulas. The concept of correctness is an integral part of the Ivy League Look, and part of what makes its history socially interesting. At the same time, there was constant innovation from its beginnings up until today, and the genre included much more than we commonly think of today. That is why the MFIT chose the term “Radical Conformists” as part of its book and exhibit on the Ivy League Look.

For myself, there are certain traditions I always follow, such as leaving the bottom button of a vest or cardigan undone. Less because it’s some sort of rule, but because I think it looks more relaxed. I also prefer to wear only single-vented jackets with buttondown-collared shirts, even though some menswear colleagues tell me that’s absurd — there’s no reason not to wear a buttondown oxford with a double-vented jacket. But since nearly all of my shirts are buttondowns anyway, it’s not an issue: I don’t currently own any double-vented jackets.

Now on to a specific example of whether or not a menswear rule applies.

The above illustration is taken from the latest issue of Free & Easy and presents (or juxtaposes, some would say) a three-piece suit with loafers. The question is whether or not there’s a sartorial rule being broken here. Some would say the formality of a three-piece suit demands a lace-up. These men would say that the loafers would look off even with a two-piece suit, not to mention a three.

Others would say it comes down to something more elusive, such as the outfit itself and the wearer’s flair for pulling it off. To hell with rules, the guy either looks good or he doesn’t. Also, there’s certainly something Ivy, or at least simply American, about this casual approach to matching shoes and suit.

So let’s see where you guys stand on the matter. — CC

[yop_poll id=”24″]

39 Comments on "Right Or Wrong? Three-Piece Suit With Loafers"

  1. Plenty of Mad Men flaunted Gucci loafers with 3 piece suits.

  2. I voted “Hmm, something’s not quite right”, but I would qualify it depends on the loafer; penny loafer – no, to casual, a better quality, dressy tassel loafer, sure.

  3. Yes, I realized when writing this that there’s a difference between a dressy loafer, such as a tassel, with a more casual tweedy suit, and a casual penny loafer with a formal pinstripe.

    We’ll just have to do our best with the basic concept of 3-piece + loafers.

  4. Loafers of any variety – by definition and construction – are casual shoes. Suits – esp 3-piece ones – are almost always formal. The two just don’t go together. Simple. It’s no more acceptable than cap toe lace ups and shorts is.

    That’s no more ‘a rule’ than eating ice cream with a spoon is – it’s just how it is. You could use a fork to be ‘creative’, but you’d make a mess…

  5. If you have to question it you won’t be able to pull it off.
    If not you won’t be worrying anyway.

  6. Mitchell S. | August 28, 2013 at 3:32 pm |

    The type of briefcase you carry also determines whether loafers are appropriate with three-piece suits. A Tokyo salaryman wearing a solid black three piece suit with loafers while carrying a calfskin attache case would look ridiculous.

    However, a more casual messenger bag carried alongside a Donegal tweed three-piece suit and penny loafers sends the right message.

  7. Depends on the suit. Depends on the loafers. A tweed suit worn in the city with a more “formal” loafer? Of course. What is the opera pump but a formal “loafer” from the days of Court Dress?

  8. Cap toe lace ups and shorts look great on girls, AEV, and pretty good on boys too. maybe not on an old toad like me, though… As regards the loafer question, surely only footballers and lawyers in television plays wear three piece suits nowadays, so the matter is irrelevant

  9. In my humble opion, loafers with sport coats, lace-ups with suits. The exception being, solid two-piece suits with BB’s tassels are good to go.

  10. I’m fine with tassel loafers and suits, be they two-piece or three piece. Since I got out of school in 1980 that’s been an acceptable, standard look here in the Midwest of the U.S.

    Nowadays where I live a man is dressed up if he has his best Green Bay Packer fleecewear on. A suit is such a rare sight that I would criticize a man’s footwear only if he had on running shoes.

  11. I think we can all agree that Opera Pumps (essentially a loafer) are one of the most formal type of footwear in a man’s wardrobe.

    My opinion the following are acceptable loafers for a suit two or three pcs;

    Johnston & Murphy’s Crown Aristocraft (still made in the USA) Westchester Tassel

    Allen Edmonds
    Adams Tassel

    Gucci bit loafers
    (preferably the old quality or similar style)

    Penny Loafers
    This is trickey, I believe that the sole, vamp, & toe are the key points.

    Plain toe shell loafer (very rare & likely the most elegant penny loafer)
    Full strap

    Allen Edmonds

    I am biased. I have never seen my father, my source for sage wisdom, best friend, & hero, wear any sort of lace ups with a suit. His go to shoe for much of his career as a litigator were the old USA made Johnston & Murphy Ski-Moc Penny (shell cordovan).

    I think the Alden 986 pair well with cotton, linen, & poplin suits.


  12. I’m in AEV’s camp. Precisely.

    I also never wore button-down’s with suits. No rule, it just wasn’t….my style.

  13. Southern Loafer | August 28, 2013 at 9:12 pm |

    Right or wrong? Three piece suit.

    End of inquiry.

  14. Roy R. Platt | August 28, 2013 at 11:16 pm |

    From the first edition (1975) of “Dress For Success” by John T. Molloy, under “Shoes That Work, The Most Popular Looks In Executive Footwear”, (the illustration shows “All Leather Slip-On”, “Wingtip”, “With Gucci-Type Buckle”, and “Lace-Up”)………

    “In the most ultrasophisticated cities, shoes with tassel or shoes with Mr. Gucci’s rather chic initials are perhaps-just possibly-acceptable for some men. Elsewhere they should be studiously avoided”.

    Although I have worn, and still wear, three piece suit and suits with odd vests, and although I have some loafers, I have never worn loafers with any suit, but I don’t see anything wrong with people wearing loafers with three piece suits (or any suits).

    I draw the line at tennis shoes with suits and with anyone who is not a cowboy working cattle wearing jeans. I have never had any jeans. I cannot imagine why anyone who is not a cowboy would wear jeans.

  15. I might wear a pair of Alden 429 shell dress penny loafers with a three piece suit, if I wore three piece suits and Alden still made the 329s.

  16. I think that some people misconstrue what a “rule” is in social contexts.

    Rules in mathematics, physics, and other such hard sciences are inviolable. Rules in squishy subjects are more akin to typically heeded guidelines.

    Of course, then we have the “break the rules for the sake of breaking them” mentality, a gift of the Communists and their fellow travelers, meaning “Progressives,” liberals of every stripe, and the majority of the Worst Generation.

    So loafers with a suit? Let’s see. Dressy loafers? Perhaps. Casual suit? It can work, depending on the suit and the loafers. Three piece suit? Hmm. I hesitate to wear bluchers with a suit,* so I have a hard time imagining even the dressiest loafers with a three-piece suit.

    As for opera pumps, since they are descended from court footwear, they have a different pedigree from loafers, and it is only coincidence that both shoes are laceless. Opera pumps and penny loafers have as much in common as a Lamborghini does with a Kia.

    *Again, it depends on the suit and the shoes.

  17. Richard Meyer | August 29, 2013 at 6:38 am |

    Agree- depends on the “loafers”. No beef roll, but IMO gucci type bit loafers and tassels can work.

  18. For me, it’s not a matter of taste, but of practicality. If it’s cold enough for a three-piece suit, it’s too cold for loafers.

  19. I agree that three-piece suits should be worn with lace ups. The only exception being possibly three-piece summer suits in poplin, chambray, or seersucker… (rarely seen but do exist)

  20. It’s a question of intent. If you know that a lace up is the accepted standard that should be worn, but choose instead to wear a pair of mocs to relax the look a little, that’s great. Hopefully the attitude of you furnishings will have the same purpose. And if you look great doing it, it means you have style!

  21. For me, a 3 piece suit calls for a shoe with a lace but I feel comfortable wearing a loafer with a 2 piece suit.

  22. It’s funny how rules, understood as a broad canon, can actually liberate one from rules, narrowly defined.

    So much goes into a suit. A suit isn’t just a suit. Cut and cloth–they matter.

    A cotton vested summer suit with loafers? Why not. More power to the wearer. This suit, whether poplin or pin/seer cord or twill, winkles and rumples in the midday heat. Even vested, the informality is obvious,

    Let’s say the suit in question is a Minnis 13 oz. woolen flannel. Oxford grey. Vested. This suit deserves a pair of Alden 9015’s. I want my banker wearing this suit. It whispers “I am reliable, I take no risks.” Add a quiet chalk stripe, and the whisper grows into a murmur.

    Don’t ask me to explain why I wouldn’t be the least bit offended by the sight of OCBD paired with a vested suit of solid worsted cloth, especially it it’s a dry-handed, low, low supers # like Minnis Fresco.

    What about a vested suit of Cheviot tweed? Now, there’s a debate worthy subject.

  23. AEV said, “Loafers of any variety – by definition and construction – are casual shoes. Suits – esp 3-piece ones – are almost always formal. The two just don’t go together. Simple. It’s no more acceptable than cap toe lace ups and shorts is.”

    Hang it, half the appeal of Ivy style is in its unique blend of formal and casual. I wouldn’t wear this particular combination for exactly the reason you describe, but I disagree with what you say as a blanket statement.

    On the subject of rule-following, you say this is “no more ‘a rule’ than eating ice cream with a spoon is” having just authoritatively stated that wearing casual shoes with a suit would be “unacceptable.” How is that not a rule?

  24. @Sartre – I’ll bite. It’s not a rule (def.: Noun; a principle or regulation governing conduct, action, procedure, arrangement, etc.: e.g. the rules of chess.) that casual shoes shouldn’t be paired with formal clothing. It’s also not a rule (see above definition) that ice cream must be eaten with a spoon. But, it’s hard to argue that either would be sensible (or – in the case of the loafers – appropriate, well conceived, attractive, or conducive to positive impressions). Do people, devoid of sound judgement and/or self awareness do senseless things all the time? Sure – typically with a dose of rationalization and/or bravado to go with it. You can find pictures and examples of people wearing all sorts of nutty stuff, couched with all sorts of ratonalization – but, the rationalization rarely makes it sensible.

    And, to clarify. Are there a couple examples of suit types that are expressly (more) casual? Yes. To be honest, I don’t wear those sorts of suits and find them awkwardly positioned in most wardrobes. The vast majority of suits are formal. The vast majority of loafers are casual. And, the vast majority of men have no idea how to dress. So, for the purposes of this non-debate, loafers and suits shouldn’t be paired. Ignorance and unnecessary risks rarely go well together.

    As far as three piece suits go, I’ve never worn one…..nor do I plan to. But, the vest, in my mind, adds to – not takes away from – the formality…..making casual shoes, in that instance, an even less sensible choice.

  25. The Weejun may not have much in common with the Opera Pump, but the Gucci Loafer is a modern-day descendant of court dress. The court being that of Captains of Industry and Masters of the Universe.

  26. I personally wouldn’t wear loafers with a “city” three piece suit, nor a button down collar…On the other hand I would wear tassel loafers with a three piece tweed

  27. @AEV – Thanks for providing the dictionary definition of a rule as a principle that governs conduct, action, etc., and then immediately proceeding to lay out the principles governing why wearing loafers and a suit are not “sensible,” “appropriate,” or “acceptable” (your previous post) sartorial conduct.

    Funny thing is, I wouldn’t wear loafers with a 3-piece either, mostly for the same reasons you state. What I object to is your absolute certainty that your way is the only way, that another way represents “ignorance” and even an “unnecessary risk.”

    As we age we begin to understand how much we don’t know, and the certainty of youth starts to crumble. Others become increasingly convinced that our way is the only way, our perspective ossifies, and the soul dries up like a parched pea. Here’s hoping that you and the other rule followers, in clothing and, one suspects, more momentous areas of life, discover the first path.

  28. It becomes clearer that schism amidst the NSS (Natural Shoulder style) ranks is a reality.

    Whereas Heyday-inspired dressers look to the late 50s and early 60s for inspiration, there’s another breed–species?–that (who) eschews the Heyday narrowness in favor of, let’s say, a broader view. The 20s, 30s, 40s, and 50s–maybe especially the Brooks, Press, Rogers Peet, and Chipp of those decades–are exalted. Can one be “Ivy” while eschewing Weejuns and narrow lapels and crewcuts and jazz composed in an alcoholic haze? Maybe not. But one can still be devotee of NSS.

    Weejuns, while worn for mostly if not primarily for leisure until the 50s, were the favored shoe for damned near everything by the Heyday era undergrads. Thus the grace granted by HeyDay heeders: if college students wore them with vested suits in 1965, then, by golly, it must be okay.

    Mad Men. Look at Roger Sterling. I imagine him a longtime Brooks man. (In reality, the suit the actor is wearing is a Brooks-by-Southwick; looks be to a Douglas or Warwick). He wears vested suits. I cannot imagine that Janie Bryant, whose eye for detail is impressive, has the WWII veteran and neat whiskey drinking Roger sporting…Weejuns. Mow the yard in them. Relax by the pool. But a vested suit? Come on.

  29. @Sarte – Do I really need to clarify or state that my comments reflect my opinions? ‘My way’ may not be the ‘only way’, but it’s the way that reflects my opinions and experience.

    There is a stark difference between ‘rules’ and things that are appropriate and/or sensible. Technically, there isn’t a rule that people can’t wear flip-flops while strolling along filthy city streets. But, in my mind, doing so isn’t sensible or appropriate. Same thing goes for jeans at the opera, shorts/baseball caps in fine restaurants, pajamas on commercial airplanes, gym clothes as casual wear, tight clothes on fat people, colored/skinny jeans on men, and so on.

    While casual shoes (loafers) and suits may not be as extreme as these examples, it’s in the same vein (and is yet another example of the hyper-casual trend where people wear whatever they want in the name of ‘comfort’ and individuality….) – not against any particular ‘rule’, but – in my opinion – simply not appropriate…..

  30. Waitaminute, so “no man looks good in olive” was an opinion, not some sort of factual statement?

  31. @CC – some of my opinions – like the Olive one – are so true they’re (very, very) close to facts/rules…..wink.

  32. I hate olive. Except perhaps the darkest shades. But this is just “taste.”

    I don’t much like the Alden tassel loafer. But it is a big step up from the Weejun. A shoe of “relaxed formality” — it was designed and marketed as such and worn by various lawyers from sea to shining sea.

    I hate lawyers, too. But this is just from my personal experience.

  33. Mr. Molloy revised the shoe section in the 1988 edition if Dress for Success. He said, “The wing tip and other plain lace-up shoes are the traditional footwear of the American businessman. Today’s’ slip-ons work just as well if they are dressy and obviously expensive.” Loafers are fine with a three piece suit – although I never wear either.

  34. There’s something about a TWO-piece suit worn with Weejuns (or was, back when Weejuns were decent shoes) that works in a “I graduated from Yale four years ago and have a job at a Washington think tank” kind of way. It doesn’t have to be a young look, George Will could pull it off. Maybe it’s a Georgetown look, though I’ve seen it in Boston. Probably not New York, though.

    Three-piece suit, though, not so much. If you’ve made the effort to get and wear a good three-piece suit, get some proper shoes to go with it, damn it. Anything with a tassel on it is not a “proper shoe” in my world, unless you’re wearing a kilt.

  35. It’s not the loafer that repels me, it’s the idea of a three-piece. I’ve always thought that a lot of luggage to carry. But, some folks seem to like ’em, so to each his own. As for loafers / slip-ons, as GSElevator remarked, “…the conventional wisdom that they lack the formality of traditional lace-ups has long-since expired.” I agree.

  36. I’ve seen guys who I think of as sophisticated dressers wear Alden tassel loafers with a suit, though I haven’t seen any of them wear three-piece suits. So, the descriptivist in me says says dressy loafers are okay with suits. Looking for consensus among people whose taste we respect is at least part of how we construct our own sometimes rickety sense of style. You get a double whammy in Flusser’s books. First, there are all the photos of stylish men of the last century, and second, the photos are in the book because they have Flusser’s imprimatur. They support Flusser’s point of view. The prescriptivist says most suits call for oxfords. And wearing a vest should preclude wearing a button-down collar, even if Fred Astaire can be seen in an ancient photo wearing one with a collar pin, no less.

    No one has mentioned the rather archaic style of laceless slip-ons that sometimes have elasticized gussets. They are admittedly uncommon, but it makes more sense to discuss them in this context than opera pumps.

  37. Evan Everhart | February 5, 2019 at 3:15 pm |

    3 piece tweed suit with Alden or Church’s tassel loafers made on a refined last, sure, but it would have to be worn with an appropriate OCBD and murky ancient madder tie, or a suitably quiet silk knit tie. I have done this myself, and I believe, there’s a photograph floating around somewhere of Dean Acheson wearing something along these lines, but, and this is a big but, it may just be my own confabulation of several photographs of the man himself.

    Regardless, for anything more formal than a rustic tweed for Winter, or a cotton poplin for Summer, the look is dubious at best. I wholly discount Gucci bit loafers myself as I detest them (clunky and gaudy looking to me, and not a good cost to value ratio in their current incarnations anyway). Suits can certainly be worn with moc toed shoes (split toe moc bluchers look great with casual suits), and loafers can look great with 2 piece suits, particularly in the Summer when worn with seersucker or poplin or fresco or mohair blend suits. But I wouldn’t ever wear penny loafers of any quality or make with a 3 piece suit.

    I do remember in the 1990s, seeing a great many lawyers wearing hideous DB olive green suits with jumbo-jet wide shoulders, and ultra low button stances wearing wing-tipped tasseled loafers in cordovan with their Windsor knotted almost tie-dyed looking brocade ties when I’d accompany my father on his trips to the courthouse on occasion. I still shudder to think of those men’s outfits, but especially their shoes….

  38. James Grant | October 29, 2020 at 6:11 pm |

    Someone (above) said: Depends on the suit. Depends on the loafer. I agree with that. You should wear lace-up shoes with a dressy three-piece suit, or perhaps tassel or brass-bit Gucci-style loafers. Depends on the occasion. Some loafers might be OK with a tweed three-piece suit at an outdoor or sporting event. Going back to the comment about not buttoning the bottom button of a waistcoat or vest – the most important consideration there is that the belt buckle should never, ever be seen under the vest. If you can see the buckle, your suit doesn’t fit. Sometimes tall guys will buy a suit in a “Long” because that is all the shop has in stock, when they should order the suit in an “Extra-Long”. Just my opinion.

Comments are closed.