Turtleneck And Oxford: The Preppy Way, And The Other Way


There’s the preppy way of doing things, and then there’s every other way. Case in point, above we have a turtleneck worn under a buttondown. Verdict: preppy.

Below (from a Valetmag.com feature yesterday), we have a buttondown under a turtleneck. Verdict: something else.

turtleneck buttondown2

Honor your forefathers. Defend tradition. Avoid forced foppery. And finally, go forth and multiprep. — CC

This post originally ran on 2/7/14.

44 Comments on "Turtleneck And Oxford: The Preppy Way, And The Other Way"

  1. Christian,

    I actually saw the pictures of the men in popped collars mentioned in the article earlier today, before seeing this article. I cringed. I’ve never seen such a think before, and I will not be one to try it. I’ll just stick to the classic way to wear a turtle neck.

  2. There’s certainly something unabashed about it.

  3. My calculus professor wears button downs under turtlenecks like this. That was the first time I’d ever seen it done in my life. Similarly to the class itself, all of the students (myself included) were very confused.

  4. Turtlemeck with OCBD and shetland sport coat or sweater longtime New England cold weather campus classic. Dartmouth, Middlebury, Bowdoin, Colby, St. Lawrence, UVM, etc.

  5. For our next trick, we will wear the sport coat on the inside.

  6. in prep school the dress code was either coat and tie or turtleneck…..always worn beneath an ocbd.

    @Christian….there is indeed something very unabashed about that popped collar. And I’m counting on AEV to chime in momentarily 🙂

  7. whoah – whoah….we’ve got a bunch of haters on here! way, way too much negative energy. hasn’t Fred taught you guys anything about layering:

    Jan. 17th: “Pablo Picasso believed that it took a long time to grow young….I am constantly looking for small ways to fold traces of my childhood back into everyday life. I spend a lot of time in my home office and I have these plastic toy soldiers strewn about my desk. When decorating my space, I tend to mix polar opposites—the masculine with the feminine (wildlife objet such as an alligator head and an Asian water buffalo horn display against pink walls, for example), the soft with the hard, the old with the new…”

    …oh – sorry – wrong one…..ha ha….couldn’t resist. Here he is on layering:

    Jan. 13th: “Noteworthy: layering doesn’t always have to start with the lightest layer. Here, a Shetland under a knit rugby jersey works just as well.”

    Nov. 6th: “Why not (wear a zipper warm up jacket) under (a) flannel (shirt)? Just because an item has a zipper does not necessarily mean it has to be worn as outerwear. It’s ok to wear your clothes with a little…what’s the word…imagination.”

    Oct. 28th: “Noteworthy: effective layering is about more than just warmth—keep it interesting by mixing up fabrics, colors, textures, and patterns. Fleece pants outside the house are easily worn when cut to sit closer to your body. Ribbed cuffs at the ankles are ideal.”

    So, case closed. You boys need some ‘imagination’, that’s all.

  8. The Other Way has an ‘Old Hickory’ feel to it. I’m OK with it.


  9. Both looks are affected.

  10. Yes, both looks are affected, but Preppington J. Tradsworth III (pictured at top) doesn’t look like a complete tool, unlike Trendyboy Preppygonewrong and his friends (pictured beneath).

  11. David Wilder | February 7, 2014 at 6:28 pm |

    Great reminder of classic, New England style. Where is top photo from? Would love a pair if those glasses!

  12. If anyones looking for a great piece of J. Press memorabilia checkout the J. Press vintage sign I just listed on ebay. One of the building men from the old store gave it to me.

  13. Yes one way is preppy and the other is something else. However, why is the other way wrong? I don’t believe the gentlemen wearing it the other way are claiming to be preppy. In fact, the pics are from Pitti and I do believe it is Italian influenced. Just because you don’t like a particular style doesn’t make it wrong. Stick to what you know sir.

  14. David Wilder | February 7, 2014 at 7:20 pm |

    The top photo if the Dartmouthish looking guy is Pitti?!

  15. @ David Wilder – please read my comment again sir. I stated the pics of the “something else” are from Pitti.

  16. The second look is just foolish, ask indicated earlier the guys look like they’re wearing 19th century stocks.

    While the first look is undoubtedly “correct”, and although I’ve seen it sported by many (including my father), I’ve never been a fan. To my eye the fellow would look better in either a turtleneck or an oxford. Am I alone on this?

  17. That’s the stupidest look I’ve seen in a while.

  18. The two belt loops on the right and single loop on the left were the sine qua non of Corbin slacks. Paired with a Gant OCBD and weejuns-the height of Ivy style in the mid 60’s.

  19. Reactionary Trad | February 7, 2014 at 11:47 pm |

    Re: the top photo:

    1. He forgot to comb his hair.
    2. The eyeglass frames are far too big for his face.
    3. The turtleneck shoul be rolled down more, so that it doesn’t protrude that much over the collar of the shirt, and so that the seam connecting the bottom of the collar to the body of the shirt is hidden.
    4. The shirt needs to be ironed.
    5. Brick-red trousers together with tassle loafers are over-kill. Those trousers should be mated with penny loafers; those shoes should be mated with grey flannels.
    6. Same goes for the belt: it should be worn with chinos or grey flannels. It looks garish with those trousers.
    7. Very nice jacket. Very nice, as are the brick steps.

  20. When I was a child in the 70’s my mum used to dress me like this. I remember wearing a turtleneck under a plaid shirt plus corduroy pants in winter. Last time I sported that look I must have been 9 years old. It probably was really cool at the time but I find it a bit dated now.

  21. Funny. I actually think the first look is absurd, and I love the second look. I could never do the rollneck under the shirt, but I am very comfortable doing the shirt under a rollneck. It has to be a thicker rollneck, though, more like a submariner, something with a little heft to it. Otherwise, yeah, it would look just as silly as the rollneck under a shirt.

  22. The top photo i’d bet was taken in the 80’s.

  23. Enter the Dickie!!!! Good God!!!

  24. Gary,

    I bet you also have a beard.

  25. Shh, I have a beard now.

  26. “Nouveau Preppy Vibe” Bout’ sums it up.

  27. @M Arthur

    Turtleneck dickies: the greatest thing since sliced bread.

    Still available after all these years:


  28. Note: you have to copy paste the entire link; just clicking it doesn’t work.


  29. what if you have Italian forefathers?

  30. and how about the banner ad right above this with the guy wearing a USA sweatshirt over a shirt and tie? Is that acceptably preppy, or something? Or doesn’t it matter?

  31. I think some readers of this website have the tendency to react against any way of dressing that doesn’t conform to their standards. Come on, guys, let them wear whatever they want. This is a free country, right? We are all allowed to have our own preferences, and judging people based on their clothes just seems superficial and immature. You wouldn’t go up to some one and tell him that he has a ghastly collar gap in real life, would you? I really think this website should be focusing on the beauty of ivy league style, instead of bashing any one who chooses not to conform.

  32. Not particularly fond of either look, as the first seems like caricature and the other is absurdist. I suppose I’d try the first, but would anticipate being mocked and asked if I was wearing a dicky.

  33. @Athlone…..beautiful! I think the guy above is wearing one! Which begs the question. “Is he the preppy way if he owns a…Dickie?”

  34. K,

    Like it or not, everyone judges everyone else on their clothing. The clothes we choose do send messages, though we might not always be conscious of them. Imagine a man in a hoodie & baggy jeans, versus the same man in a suit & tie. Which one of them might you cross the street to avoid? Which one would you trust your money to at the bank?

    Far from being superficial, clothing often tells us about who is inside them. Far from being immature, it takes a degree of maturity, and even wisdom, to learn what to read into someone’s clothes, and how much to read into them.

    That these generalizations are not true at all times does not negate their validity.

  35. @Reactionary Trad — you are off base on every count but #7.

  36. “nouveau preppy” – Seems rather contradictory.

  37. Well, the men shown below may look much more handsome than the boy above with his awful eyeglass frames – which might influence the judging of layering sequence. For me it is obvious that a turtleneck never belongs over a button-down shirt, but always underneath – I do not even wear shirts when it is too warm for wearing a turtleneck underneath. But I agree with “Reactionary Trad” that the turtleneck collar should be folded lower down, and not protrude more than a few millimeters above the shirt collar, when the collar button is left undone. But I also like the proposal of many fashion designers to let the turtleneck peek out by half an inch or so from the fully buttoned shirt collar, even sometimes with a tie added – although this offers quite a daring look; anyway recently when I had to go to a wedding I wore a white turtleneck hidden under my white shirt (with tie) by buttoning the latter above the turtleneck collar

  38. When I was in high school, (1960’s) a guy I knew wore a turtleneck under a OCBD. He was a real jerk.

    Wear it if you like. Doesn’t look right to me, though

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  40. DCC –

    You are not alone. Living in New England, the turtleneck is standard fare during the fall and winter months. Although we do love layering–for both practical and sartorial reasons, like you I’ve never been a fan of the turtleneck under an OCBD. Many of my friends and family wear it like this, but I have always prefered simplicity: A turtleneck under a crew neck sweater or, occasionally, underneath a sport jacket. Turtlenecks are typically made with a denser cotton than an OCBD. It seems to violate the layering principle of lighter weight under the more heavier layers.

  41. I submit that what’s off-putting about the guy in the first pic (oversized eyeglass frames, etc.) really stems from the era when the image was taken, which one must presume to be the late 70s/early 80s.

    The guys in the second pic, however, are either going for something hyper-retro (ie. some kind of 19th century wing collar look), or simply being absurdist. Just because you *can* layer things in any order, doesn’t mean that you *should*.

  42. Whoa, this is all wrong. The fellow on the top has his belt on backwards, trousers are waay too long, & he looks like an extra from ‘revenge of the nerds’. The guys below look no better; euro trash, at best. Think polo, turtleneck, oxford, sweater, & then down vest or sport coat. The idea is to stay warm while out of doors…….

  43. What do I know, but they both look ridiculous to me.

  44. I grew up in pretty much the epicenter of ivy style clothing in Concord, MA in the 1960s and 1970s. This turtleneck under an OCBD was practically the uniform of school boys during late fall/early winter. It is as traditional Ivy from that time period as you can get.

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