Elegance Week: Oak Street Bootmakers’ New Bit Loafer


Bit loafers are one of those polarizing items in the genre. But love them or hate them, they’re certainly a step up in sophistication from penny loafers (which is why the OPH calls them “strictly post-collegiate”). We last featured them on Ivy Style with this photo of Fred Astaire, who is surprisingly sporting them with double-breasted flannel suit, oxford buttondown and satin tie (a recipe for elegance right there).

On Tuesday Oak Street Bootmakers released its new bit loafer in black and brown. Made in the US of Horween calfskin, it is priced at $328. That’s a fair price for American-made footwear that shouldn’t polarize anyone. — CC


39 Comments on "Elegance Week: Oak Street Bootmakers’ New Bit Loafer"

  1. A. Thomas Ward II | October 23, 2014 at 11:39 am |

    Looks just like the Alden Cape Cod. Wonder how it differs in quality, if at all?

  2. Bags' Groove | October 23, 2014 at 3:13 pm |

    Snaffle-bit loafers must be in suede, and must come from Gucci. Still the original and the best. Black with silver go spiffingly with dinner garb. I look an absolute delight.

  3. I’ve had the pleasure of purchasing a couple of pairs of shoes from the gentlemen at Oak Street Bootmakers. The first pair was their natural beefroll penny loafer on their website, and then I stopped in their store in Chicago. Oak Streets designer was there and we chatted a bit. I picked up the camp moc – made of Horween leather just like Beans used to be!

  4. I’ll have to stop by the store and check these out. They look good. Everytime I am in Hong Kong I see the main-landers wearing Gucci. Ruined the brand for me. They are a must have part of the main-lander rodeo clown look these days.

  5. @A.Thomas – The vamp on the Alden bit loafers seem to be lower than the OSBM shown. Though, I only wear Gucci bit loafers in black, brown or brown suede in the classic style.

  6. A three cornered hat goes very nicely with bit loafers.

  7. M Arthur


  8. Comments by M Arthur and E added two more reasons to dislike bit loafers to those given here:


    They do look great on gals, though.

    So do low-waisted pants, pink shirts, extra-slim shirts, tight pants, and other items that have no place in a gentleman’s wardrobe.

  9. Bags' Groove | October 24, 2014 at 3:32 am |

    @ Curmudgeon

    A “rare delight”???
    Frankly, I could not believe what I was reading much of the time. What did poor old Gucci ever do to warrant such treatment? Though I suppose those “negative comments” could also be levelled at Alden…and now Oak Street…non?

  10. Whether it’s because of my gender or that I grew up on a horse farm, I love bit loafers. I’m also biased because loafers are among my favorite styles, and Oak Street Bootmakers and Horween are both located in my city. I added Oak Street’s new bit loafers to my wish list after opening their email announcement this week–they will be the perfect addition to my ever-growing collection.

    I agree bit loafers are a mature shoe and often look strange on a younger individual, because a refined style and mature closet take time. I also agree think they are dressier than penny loafers, which is why they are on my wish list this winter. With socks or without is always a fun debate.

    On the other side of the coin, if you do not have an affinity for the style I can understand why: they often come off as too much or ostentatious. Dress authentically for you. Not everyone feels comfortable in a paisley tie, and the same is true for bit loafers. It is painfully obvious when someone isn’t at ease in their clothes, so don’t wear it if you don’t love it.

  11. @ Thody Evans

    Pink shirts “have no place in a gentleman’s wardrobe”? I would perhaps argue that the first things a gentleman should banish from his wardrobe are hidebound, pedantic, imaginary rules.

  12. I’ll second that

  13. It’s rules that prevent flip-flops, overalls, bolo ties, wife-beaters, etc. from qualifying as “ivy”.

  14. You need rules to tell you not to wear overalls?

  15. idontlikeracists | October 25, 2014 at 2:03 am |

    Your racist comment is uncalled for. The so called mainlanders that you despise are running that little city of Hong Kong now; no matter how much snobbery you display to try to set yourself apart from the “main-lander rodeo clowns”, your former British imperial colonizers are not gonna relieve you from your new masters. Power dynamics is quite interesting, isn’t it?

  16. Chapter Two | October 25, 2014 at 3:44 am |


    Mainlanders and Hong Kong Chinese belong to the same race, so referring quite accurately to mainlanders as clowns can hardly be termed racism.

  17. @DCG
    My point was that some people seem to think that anything goes. I assure you that the day will come when BB’s Black Fleece and J. Press’s York Street will feature overalls.

  18. I won’t disagree, but I think forming taste is different from following rules and more important in dressing well, whether Ivy or not. It’s similar to morality, there are rules, then there’s conscience. Forming one’s conscience is a personally responsibility, and you can follow all the externally imposed rules and still have no interior moral compass. Take away the enforcement of rules (sartorial inquisition? Maybe we need one…) and you’re left with your own sense of right and wrong, in morals and in footwear.

    I might just have to pursue this: the philosophy of menswear, from St. Thomas Aquinas to Thom Browne.

  19. @DCG

    “The apparel oft proclaims the man”.


  20. Vern Trotter | October 25, 2014 at 1:48 pm |

    Old Ivy Style saying: “Pink makes the girls wink!”

  21. @DCG

    Excellently put.

  22. DCG,

    Interesting perspective. I would like to read that. Are you saying that it would be bad if men dressed well because they followed a set of rules instead of their sense of style?

    I think that rules are important. They are especially helpful when someone is first learning about subject, sport, or game. I also think that you are right that as you become more experienced there is more room to interpret how these rules apply to you and whether or not you will obey them. They are only rules not laws.

  23. Apparently we are no longer allowed to criticize anyone, unless they’re white, in which case we’re not allowed to praise them.

  24. A.E.W. Mason | October 25, 2014 at 4:25 pm |

    Picking up on DCG’s forthcoming book on menswear, there is a direct temporal correlation within the white shoe legal world (which is no longer a profession but just another business) between the gradual decline and almost disappearance of the 3-button, natural shoulder style and the gradual decline and almost disappearance of civility and ethical standards. Are they related in some way? Oh, who knows.

    Anyway, on a much more important note, a happy posthumous 100th birthday to American poet John Berryman. He dressed pretty well “whilst” at Cambridge and for several after years when he came back to the States. Alcohol, perhaps?, ruined his style thereafter.


  25. Black, low vamp loafers of any variety are terrible. Beyond that, these appear to be an exact copy of Alden’s interpretation, which at least had the decency to lower their vamp as to not be an exact copy of the Gucci model…

    Black, low vamp bit loafers with a double-breasted suit as “elegance”? Lord.

    And why, CC, do you insist on quoting references in the OPH as if they’re anything but pure parody (if not mockery)…..?

  26. Oh, the old “OPH is satire and therefore inaccurate” argument so often seen on Andy’s Trad Forum.

  27. For those tyros who don’t know what loafers are:


  28. The people I grew up with were the very people parodied in the OPH, but I clearly recall seeing them wear Gucci loafers in college. I never quite understood the appeal of bits on loafers. Comfortable (Gucci)? Definitely. Stylish? Maybe. Besides, it was the girls who were into horses.l

    And based in the many references to it here, I finally figured out what Ask Andy’s was. Its discussions looked more than a bit like the sorts of things I wondered about when I was 14 or 15, but was afraid to ask anyone about, although I suspect that the AAAC posters are a bit older.

  29. As a farm boy who had grown up in Oregon, TOPH provided me with an introduction way of life that I had been totally unaware of and allowed me know how to dress in order to fit in perfectly when I got a scholarship to Princeton. I am forever indebted to Ms. Birnbach.

  30. Bags' Groove | October 26, 2014 at 10:33 am |

    Something for deep Sunday sartorial contemplation. Snaffle-bit or tassels (with or without unmentionable fringe), or, and this is where it becomes totally scary, without any adornment at all?

  31. I didn’t suggest it was “inaccurate” (though many have). What I said is that it’s largely parody and mild mockery – which it is. And, which makes it an odd (repeated) reference on a blog looking to assert itself as a place for serious and credible analysis, advice, and debate.

    Not unlike profiling and admiring low vamp black loafers.

  32. I interviewed the author of “The Official Preppy Handbook,” and the interview was included in the press kit for her recent sequel. When I asked her about the tone, I recall her calling it “lovingly irreverent,” which seems an apt description. It should be regarded with equanimity as an important cultural document. The proper regard of it is one of neutrality. It is neither to be followed as scripture (though it’s certainly functions as a breviary for those who need it), nor need it be regarded with scorn. It’s simply a cultural and historical document.

    As far as “a blog looking to assert itself as a place for serious and credible analysis,” we stopped having to do that about halfway through year one.

    And as for low-vamp black loafers, please see the first sentence in this post.

  33. @ idontlikeracists

    “main landers” is a racist term? Please. Try again. I have yet to see anyone from Main Land China dress with any form of style or taste outside the select commie few who have raped the country and brainwashed idiots like you. Most ABC dress as poor as the rest of the country here.

    Hong Kong – people said the same thing about Berlin. Guess what? Where’s GDR now? How about the USSR? Oh right, they don’t exist. Xi is having quite the fun time reeling in the faithful who destroyed pretty much the sould of China.

    I stand by my remarks. Spend a day in Kowloon and laugh at the bumpkins from across the border. It’s fun. Throw a name brand lable on anything and charge three times the price for everyone who isn’t speaking Cantonese. TST is a fashion nightmare of fools dressing to impress other clueless fools.

    Then there was the Main Lander couple who held their child up in an MTR station trash can during rush hour while he shat. That was a hilarious video. If Hong Kong ever fails, the remaining sliver of real chinese culture goes with it.

    China is it’s own enemy. Sit back and watch the implosion.

    Now go back to a state approved website.

  34. AEV gets it. If yo are quoting teh OPH as a source then you really don’t get it. And you are probably someone who has way too many rules and no personal style…

  35. I attended a book signing where Ms. Birnbach was asked various questions by attendees. She unequivocally stated that the (original) book was to be taken as parody. It shouldn’t, frankly, require author interviews and Q & A to surmise as much. Irreverent and “parody” are not contradictory.

    Sure, bit-style loafers aren’t for everyone. Low vamp black loafers of any style are for no one. If folks enjoy bit loafers, get the (Gucci) originals, in non-black, with a vamp that doesn’t flirt with toe cleavage.

  36. Upton Sinclair said of “The Jungle” that he aimed for the public’s heart and hit it in the stomach.

    Bit loafers as “post-collegiate” seems quite accurate.

    I mean, except for this girl:


  37. Ne Cede Malis | October 28, 2014 at 7:28 am |

    TOPH is pretty tiresome at this point, but hey – absent that book it is highly likely that the village in Weatherford, Texas would still have its idiot.

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