If The Shoe Fits, You Got At Least Something Right

Was at the gym  Saturday morning.   Guy walks in with a shirt that looks like it came in a spray can.   I always carry a bag, the bag has a notebook in it.    Here’s what I came up with:

Bro you are not an Avenger.

In working with Dylan and Duncan (and Elena, which is a whole other story – all I can say is that if you really really want to get into shape try keeping up with a dancer in your workouts) my body has changed.  My clothes fit better.  Which is great, yeah yeah yeah, but …  shouldn’t clothes just always fit anyway?  Isn’t that what tailors are for?

That is different from the fact that my clothes look better, they do.  But that isn’t fit.  In theory, all clothes can fit.

Fit is comprised of three components.  The first is comfort.  Why?  Elegance.  You never saw an uncomfortable elegant person.   There is a faction of Ivy that doesn’t care so much for comfort.  That’s silly.  Ivy was just an itch in fashion’s pants until somebody said, “You know, this shirt is even more comfortable untucked with shorts.”  There is a faction of Ivy that takes actual pride in being uncomfortable.  I suspect that faction lets the uncomfortable thing bleed over into other areas as well.

Where some other styles all out of my favor is when they stop at comfort.  Fit must be comfortable, but it also must be also be an upgrade.   No one should look better with their clothes off.  If you do, don’t wear clothes.  And you know what I am saying.  Fit must create lines.  Now.  Whether we like to admit it or not, the human eye prefers for the most part certain aesthetic rules.  Ask any good architect.  You can collect these rules and submit them to the test of time.  If they still stand, then you have a classic on your hands.  Another reason to love Ivy, if dignity is not your thing.  The frame and shape of most Ivy is classic.  Ivy fits.

The third component to fit is that how well each piece communicates with each other.  Too loose a collar and a necktie looks droopy (unless you unbutton the collar, go degage).  Too tight a waistline and your shirt looks like an upside down umbrella.  Too long a tie and your pants look too high.  Or too low.  Too long a tie messes up a lot of other things.  Socks too short = pants too short.  If you have to do socks at all.  Etc.  A single piece can fit, but unless it is talking to the other pieces and making them fit, what’s the point?

Kevin Cortez over at Reviewed (here’s a link) did some work on how masculine clothing should fit.  He worked with two tailors, Stacie Pettersen, head stylist and manager at Beyond Bespoke Tailors in Manhattan, and Joe Holsgrove, coatmaker and tailor at coat maker at Dege & Skinner located on Savile Row.  In his article, Mr. Cortez went to the trouble of explaining what Savile Row is.  Draw your own conclusions.  Still, there are a few notes that are worthy of our discussion here.

  1. Pettersen says one finger between your collar and your neck.  I read an article in GQ in the 80’s that said two fingers, that has always been my rule.  Mr. Cortex goes on to point out that unless you can get a finger in there, you are choking yourself.  I submit that is something I would know anyway, but perhaps he had a word count he had to get to.  Which would also explain the Savile Row thing.
  2. This is a quote from the article:  “The sleeve length of a men’s dress shirt should land where the base of your wrist meets your hand. There must also be a half-inch of gathered fabric near your wrist so that when you extend your hand, it doesn’t show forearm.”  I am not sure how you pull that off where that half-inch comes from.  But I do know this.  If you are not wearing a wrist watch because it is messing with your cuff, your watch is too big or your cuff is too small.  You pick.
  3. According to Mr. Cortex, you should be able to bend your arms.
  4. Here though was a good rule of thumb.  If you have a hard time finding things that fit, buy the piece that fits the biggest area and then tailor everything down from there.  Now, this comes from tailor.  But it makes sense.
  5. Ok, I try to take it easy on fashion writers, but this is one of the reasons I am such a Boyer fan.  He CAN WRITE.  Here.  Mr. Cortez moves on to how a jacket should fit, and tells us, “The most important parts of a jacket’s fit, Pettersen explains, are in the sleeves, shoulders, and body.”  In his book about doors, he says, “The most important part of a door’s function is it’s ability to open and close.”
  6. But they do offer something, I tested it, and it works for me, see if it does for you maybe.  They say that you should be able to fit a fist into your jacket at the lapel.  Any more, it is too big, any less it is too small.
  7. Stacie Pettersen is an interview I need to get.  She is talking about jeans.  “The waist should fit completely—there should be no gaps at the waistband,” she says.  She goes on to say that a belt is just jewelry for your clothes, that it shouldn’t hold your pants up.  I totally disagree.  I never go without a belt, and it holds my pants up all the time.  I even tie the string on my bathing suit.  You?  Ms. Pettersen says that the hem of your jeans “… should appear clean. It should also fit comfortably around boots just as well as flat shoes or sneakers, without any extra fabric hanging out.”  What extra fabric?  Isn’t that the point of the hem?  I am missing something.  I will call her.
  8. This is totally unrelated, but one of my fashion resolutions for the year was to not wear jeans at all all year.
  9. Pettersen and Holsgrove disagree about slacks.   Here’s something you may not have known.   “The very term ‘slack’ derives from the Saxon word for ‘loose’, and as such, these garments should fit that way,” Holsgrove says.   Ms. Pettersen likes them tighter and tapered.

The feature image is a shirt that fits.  It is a Polo polo, because that book is coming out and I am into it.




27 Comments on "If The Shoe Fits, You Got At Least Something Right"

  1. Another interesting post. “Pulled together” is the term my late maternal grandmother used to describe not just looking presentable but, as you say, each item communicating with the others worn for any given day or occasion. This is where so many people stumble. One or two things throw off the rest of the overall look. Mental discomfort too can undermine efforts to dress presentably. Pained facial expressions and stiff, ill-at-east movement are the tell-tale signs even if/when sizing is correct, and some attempt has been made to coordinate items making up a particular ensemble. You’ve got to wear the clothes more often than once or twice a year to feel comfortable in them as so many have noted elsewhere already.

    Kind Regards,


    That is so true. Otherwise it is like driving too much car. You have to have familiarity. Good point. – JB

  2. #3 is a real eye-opener.

    JB – I’m on the no jeans program as well. Haven’t worn denim for a few years now. One of the greatest marketing scams was convincing people that jeans were comfortable and durable.

    You know, now that I don’t wear them, I gotta say, you are 100% correct. There is no way jeans are as comfortable as khakis. – JB

  3. Regarding fit:
    Someone more skilled than I could (should?) write a piece in favor or the old, old J. Press (New Haven homage to old Brooks) sack. With its roots in English Country life,* it serves as a middle-fingerish rebuke of the overly fitted/tapered look that’s become “fashionable” (just threw up in my mouth a little bit). No one can blame JFK for wanting some extra shoulder padding and a tapered middle to seem fit and erect, but hasn’t it gone too far? I’ll blame “designers.”

    * I hoped for a revival during the Downton Abbey moment– note the tailoring of Lord Grantham’s clothes, (as well as Tom’s).

  4. Hardbopper | May 11, 2022 at 10:45 am |

    I haven’t thought about it until now, but Stacie Pettersen’s advice is probably applicable to women’s jeans, fit at the waist, and belts, for obvious reasons. On hems, she is referring to “cloth puddles”.

    Maybe it is just to objectively obvious, but I just realized the correlation between comfort and elegance, Thanks.

  5. Frederick J Johnson | May 11, 2022 at 11:50 am |

    Somewhere some time ago, someone wrote about the correct relationship between the width of the trouser bottom in relation to the length of the shoe (shoe size?) I wonder if any of the readers here recall the ratio. I have seen far to many men where something is off and the wearer looks as if he’s wearing skis.

  6. Hardbopper | May 11, 2022 at 11:54 am |

    On #4. “…buy the piece that fits the biggest area and then tailor everything down from there.”

    That is on off-the-rack, rtw assumption, it probably will not work, and it will not be stylistically correct. You’ll end up with buyer’s remorse, time wasted.

    I would go one better. IF THEY CAN still source the correct style, get the best piece you can afford, MTM, from O’Connell’s, making sure they are a tad generous in the measurements, and THEN tailor down from there, only if necessary.

  7. whiskeydent | May 11, 2022 at 12:43 pm |

    I recall a discussion but I not a specific rule.This is a constant concern for a guy who wears a 14. Tapered pants can give me clown shoes, especially if I’m wearing gunboats.

  8. whiskeydent | May 11, 2022 at 12:44 pm |

    I’ve gotta get new glasses.

  9. Hardbopper | May 11, 2022 at 2:25 pm |

    It depends on the shoe, but let’s assume a classic long wingtip blucher. https://vcleat.com/.
    The “width” at the hem should be “wide” enough, to meet the shoe, with very little to no break, where the eyelet tab meets the vamp.
    If they are a bit “wider”, that’s ok, too, but not so “wide” that they extend to the back of the toe cap. Any smaller, they will puddle. So, using this diagram, I’d say the “throatline” and the toecap “broguing” line would be your “long and short” limits. https://www.patyrns.com/blogs/mens-fashion-blog/what-every-gentleman-should-know-about-shoes. (I know, this isn’t a longwing blucher, but it’s the best diagram I can find for this comment).
    Generally, a bit bigger with gunboats and a bit smaller with loafers is good for ‘ratios’.
    I suggest you buy a cloth measuring tape, and some safety pins and straight pins. Remember that when the pants are worn, that will greatly affect the “width” measurement (from the back crease to the front crease), so there must be some compensation, because at that point you are dealing with a creased circumference. You can make a template of sorts. Maybe cut the bottom off a very worn-out pair of pants. You can get the measurements as exact as you’d like and then do the math to determine a ratio, but “tailors” are going to go by 1/2-inch increments at best, and won’t understand ratios.
    (I use quotation marks because I don’t conceive of that measurement from back crease to front crease at the hem as width, as it’s more of a diameter).
    Man, technical writing is tough.

  10. whiskeydent | May 11, 2022 at 3:34 pm |

    I wear my AE 5th Avenues when I try on pants and get them cuffed so I can avoid all the rocket surgery you just described.

  11. “Guy walks in with a shirt that looks like it came in a spray can.”

    Athletic clothing has come a long, long way since Ivy’s halcyon days. Often times synthetic, stretchy athletic garments are intentionally tight-fitting so they are moisture wicking.

    I’m not suggesting anyone needs approve of the aesthetic. I certainly don’t wear my Bjorn Daelie gear in any situation I have the slightest suspicion I won’t also have skis on my feet.

  12. As a follow-up, J.B., the intro above is kind of weird. You want your gym clothes to create flattering lines? Seems like overkill. Just bring a gym bag, and change in and out of them in the locker room.

    Oh wait. You change in the LOCKER ROOM? Man. Wait. Where do the women… oh the WOMEN’s Locker Room! Imagine all these years, all of the embarrassing incidents, not to mention tickets, I could have avoided, IF ONLY I KNEW TO CHANGE in the locker room! So that’s how a gym works. Thank you.

    As a favor in the future, could you at least wait until I make a real mistake? You must have dislocated something reaching for that. In the event that you did, and you have to go to physical rehab, here’s what you do. You bring a gym bag, and change both IN and OUT of your clothes in the locker room. – JB

  13. Tennis shirts are cool, but I never understood why wearers would pop the collar so that it stands up.

    Sprezzatura, like most things, can be taken too far.

    I never understood until I owned a boat. You come off a boat, the wind has flipped your collar, it is a cool look. But tennis, I agree. It’s not my jam either. – JB

  14. AndrewK247 | May 11, 2022 at 7:23 pm |

    Regarding #2 – that is one area where “dress shirts” in neck/sleeve sizes fall short compared to alpha-sized “sport shirts”. Specifically sport shirts tend to have 2 sleeve buttons, while dress shirts have only one. I dont know why the hell a dress shirt can’t have 2 buttons. Unless you get your shirts custom made, the button will probably leave an opening that is too wide.

    I’ve been measured as a “33” sleeve, but when I reach out to shake hands or pick something up, it rides up too far. So I switched to “34” and wash it once in hot so that it is not too long, thought it still is slightly.

    Hi! I am lost, but it is me. I am not understanding. Seriously, it is me. Do you mean two buttons on the cuff? If that is what you mean (and again, not being a tool here, I am really just not understanding and I am 100% sure it is me) – that is a REALLY good point I never thought of before. Why can’t they have two? – JB

  15. AndrewK247 | May 11, 2022 at 7:28 pm |

    Side note on @2 – if you are not sure if your watch is too big, it is.

    Also, for 75% of guys reading this – your watch is too big.
    Look at old pics from early 60’s especially – the watches look elegant.
    Now even on the watch blogs, even most of the “experts” wear watches that are way too big.
    The diameter should not be as big as the width of your wrist.

  16. Mitchell, I believe the practical reasoning for a collar pop is sun protection whilst engaging in your activity. So, as most things, the practical and easy solution gets emulated for the perceived cool aesthetic and inclusion into the group.

  17. JB, I’m green with envy: a home on Nantucket AND a boat? Wow.

    Recently I saw an interesting video on YouTube about how to dress on vacation in Nantucket. GQ had a similar story years ago.

    Since you are an expert on Nantucket, I am interested in your perspective. I heard that it is common to roll up the bottoms of your Nantucket reds, rather than have them hemmed or cuffed

    Boat yes. Home on Nantucket = rented. Cuffed Nantucket Reds mean… you just got here. It’s ok, maybe you mail ordered them from Murray’s. But now that you know better, please do get rid of them. And by that I mean you can either hem or roll them. You need more than one pair. You need the pair that you wear with a blazer. Those can be hemmed. There are some spots on the island where you just can’t roll. What are we? Animals? But you need a pair that you can roll, too. Because there are some spots on the island where you just can’t hem. How do you know the difference. Look left. Look right. You’ll get it. Another thing about Nantucket. It is WAY friendlier than the money would have you think. – JB

  18. AndrewK247 | May 11, 2022 at 9:11 pm |

    @JB – Yes, I should have said two buttons on the cuff. Forgot the word “cuff” lol.

    I’ve seen a few shirts with 2 cuff buttons, mostly from less expensive brands, where the sleeve is labeled as 33/34 for example. Theory being that if you are 33″ you leave the cuff opening larger and if you are 34″ you make the cuff smaller so it does not hang over your hand. They have to pay for 2 more buttons on each shirt, but they only have to make 1/2 as many sizes. Don’t see why the upscale shirt brands can’t do this.

  19. AndrewK247 | May 11, 2022 at 9:46 pm |

    Sorry I got the theory part backwards. If you are a 33″ you make the cuff smaller so the sleeve does not hang over your hand.

  20. JB, thanks so much for the tutorial!

    Yes, Nantucket is definitely way friendlier than Puritanical old Boston.

    I read that *all* beaches on Nantucket are now topless beaches:


  21. Frederick,
    Just measured what I think are just right cuff width as described above. 9.25” from crease to crease, or 18.5” circumference. Gunboats are 12.25”. So the ratio is approximately 3:4, creases to shoe length, or 2:3, shoe length to hem circumference, 18.5” total. Too big for wearing with loafers in my opinion. These chinos are very cool and comfortable, but too baggy in the thigh, double forward pleats. I think the Donnelly chinos are 17.5” so I am going to get a pair of those to wear with loafers for a more Ivy look.

  22. Interesting commentary re: the Murray’s Toggery Nantucket reds. It evinces exactly why I’ve never bought a pair, in spite of my occasional interest in doing so. The rules are so specific and so borderline ridiculous that my reluctance now seems even more warranted: If you’re a member of a yacht club in Nantucket, the wearing of such pants is obviously sanctioned. But woe unto the wearer who rolls or hems incorrectly, or whose memory of how to tie a proper bowline is slowly fading in the mists of time. Such people are interlopers, or poseurs at best, clearly doing it all wrong, and probably lousy sailors at that. Maybe I’ll break down and buy the blue or green ones they sell. Nobody will know they’re reds when they’re a different color, and I can hem them to my liking without the social consequences.

  23. @Mitchell — The popped polo collar can certainly be a silly try-hard style affectation, but the original purpose as I understand it is to keep the sun off the neck. (This may be apocryphal, as so many menswear backstories can be.) Polo collars are remarkably good at sun protection when they’re popped up. I’ve only ever worn them that way on my kayak or while golfing, but it works if you’re not fully trusting your sunscreen’s longevity.

  24. Sun beating down on your neck, polo collar up.
    Two buttons on shirt sleeves, mid management?
    Large watches, Hummer drivers?

  25. @Nevada:

    I’m with you; I was thinking the same thing myself.

    When I called Murray’s Toggery Shop on Nantucket, the owner/proprietor told me that the “correct” way to wear reds on the eponymous isle is to have them cuffed at EXACTLY 1.5 inches. This is ridiculous!

    Now, thanks to John, I know that this will make me look like an arriviste or a poseur.

    John, thanks for the advice, but I will not be buying any more Nantucket reds, thank you. I will keep wearing plain old chinos from now on…

  26. Hi! I came across this website and I’m confused, do you sell clothes or just talk about them? What is the membership for? I noticed that some of the links don’t work or have no content so I’m left with many questions. Hoping you can clear it up for me. Thanks!

  27. Thomas Lee | May 16, 2022 at 1:49 am |

    Kathy m.

    You are really confused!

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