Fiending for Fall


You can almost feel fall in the air. You can most certainly feel the anticipation in the air. Since it’s not quite cool enough to toss on a pair of cords and a shetland quite yet I thought that I would add to that anticipation and pose a question. The pictures are the anticipation and the question is, what are you looking forward to this fall?

IMG_2436Rugged PreppySweater and Repp TieShetland sweater with vestIMG_5470IMG_5404IMG_7134Trad Shirt JacLight Green ShetlandIMG_5596Shetland Sweater in SalmonIMG_2306IMG_1627

Why Won’t My Collar Roll?


Why won’t my collar roll? I can’t count how many times that I have been asked this question and it does not come without good reason. The perfect collar roll is one of the trad/ivy style features that we all chase. In this post I will go over the two most common issues that I come across when analyzing that roll.

IMG_8509If you are are here and asking this question you already know what collar roll is. For those of you that don’t know check out my “What is Collar Roll?” post that I did way back when. Basically collar roll is that mesmerizing arch created by a tie and a button-down collar.

1. Your shirt is too big.

This is by and far the biggest reason that I see when people ask why their collar does not roll. It is also something that I have a lot of personal experience with. In order for the collar to roll the collar must be snug. Not so tight that you can’t get a two fingers between the shirt and your neck, but almost no more room than that. It is the pressure between, the tie, the shirt, and your neck that forces that roll. If there is too much space or material between the collar of the shirt and your neck it will not create the tension required.

Collar Roll Example

2. Your collar is too short.

I have found that any collar point length under 3.25″ is going to be a challenge to get to roll. The reason is that there is not enough material to get over the tie knot and roll. You could have all the pressure in the world here, but if there is not enough actual material to roll you are out of luck.

These are the top two reasons that I see time after time when asked about collar roll. This is not to say that these are the only issues. Even when you get the perfect fitting shirt you may run into some issues. If this does happen try the solution suggested by Charlie Davidson of the famed Andover Shop (Thanks, Blucher Moc!) which is to move the buttons a little bit (See here). Whatever the type of collar roll you are after I hope this helps you get there!

OCBD Wears Denim


Yep. You read that write. I have went where very few trads have gone and returned…denim.

All joking aside I haven’t worn any type of denim in a very long while (meaning years). I won’t even say that I missed them. I don’t find jeans nearly as comfortable or as versatile as chinos, but at the same time there are casual situations where they will come in handy. Don’t get too worried I didn’t go with blue.

wheat denim ivy styleI kicked off my return to denim with two pair of Levi 501s that I purchased at an outlet for around $40. I got one in white and one in wheat. I thought that these colors would be easier for me to work into my look than blue. I have posted about wheat jeans and there ivy roots before (wheat jean post). Everything that I said in that post about wheat jeans there I will say applies to white jeans as well. Basically west coast ivy roots. Think madras, surfing, and the Beach Boys.

White jeans with madras So there it is. I did it. No strong opinions. I did find the wheat denim easier to wear than the white. I also found that tucked-in worked a lot better than untucked which I do a lot when I am off duty. Oh and with the white jeans I liked blue gingham and madras. I didn’t get much feedback on either, but I think that people liked seeing in something outside of chinos.

How to Prep: The OCBD as Outerwear


I figured that I would write about this while it is still warm enough to wear a polo shirt. I also know that I will probably catch some flack and/or ruffle some feathers with this. I am okay with that. This is stuff that I really do.


OCBDs (oxford cloth buttondown shirts) make great lightweight jackets. However I have found that they really only work over polo shirts (or even t-shirts in a pinch). I have worn them with polo shorts and chinos as well as shorts (and yes gym shorts on occasion).


When does this make sense? This is not a combination that I would wear all day, but more of a short-term solution. A few scenarios might be in the morning when it hasn’t warmed up, the evening when it had cooled off, or in a light rain. I think that accounts for all of my pics


This post reminds me of how preppy people tell me that I look on occasion. This happens a lot when I run to the store in gym shorts and boat shoes because my boat shoes were by the door or when I wear throw on a polo with my athletic shorts. Sometimes preppy just happens. I think that this is an example of that.

The University Flap Pocket


The flap pocket OCBD is a hallmark of the trad and ivy looks. Those in the know tend to know that if you are wearing a flap pocket that you know what you are you doing. We know that the shirt probably comes from J.Press or is a custom OCBD with a wink and nod to Press. I myself am a fan of the flap pocket, but not necessarily on the standard blue OCBD.

IMG_0533 - Copy

While I own several flap pocket OCBDs there is one that I wear more than any other. That one is a red university striped shirt. There is something very unique about the pairing of the university stripe which is sometimes called a candy stripe with a flap pocket. It can’t put my finger on it, but it just works. While I love my red one I think that it would work well in blue, pink, or any other color that you can get your hands on.


Here is why I don’t love my blue OCBDs with flap pockets. Before I say this please know that is very unique to my specific look and that I have the utmost respect for those in the armed services. I find that these shirts look a little military on me. Again this has to do with the haircut, my build, and potentially something else that I am unaware of and it’s not just me. I have been asked several times while wearing this shirt if I am a military man (often Air Force for some reason?). If you are not as clean cut looking as me this may never ever be an issue for you. In fact if you are not very clean cut the flap pocket will look even cooler on you like I think they do on me when I have my beard.

I picked up my red university stripe OCBD at Michael Spencer. However, I think that you should be able to recreate this shirt at any of the custom spots such as Ratio, Mercer, and probably quite few others that I am leaving out. The funny thing is that while my shirt is definitely a nod to J.Press it is not available there. They only offer their flaps in solid colors.