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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.

Lay of the Land


There is going to be a decrease in pictures of me in ties, blazers, and sport coats. I hope that this temporary, but only time will tell. Wondering why? Well the reason is that I started a new job last week.


I have written about this before, but it’s worth revisiting. Ties, blazers, and sport coats are tricky in the modern office. This is especially true when you are not upper management. There are all kinds of connotations and associations that go along with these items and while that is not necessarily your problem you may feel the consequences.

My advice is to play it safe. Take stock of who wears what and try to understand the office norms. If ties are the standard you are golden. If no one wears ties including all of the directors and VPs it may be best to hold off until you have established yourself. Of course you can always throw caution to the wind, but you may end up keeping your tie and losing your job.

So for the meantime I will be in my basic uniform of blue OCBD, plain-front khaki chinos, penny loafers, and olive surcingle. Luckily for me I am okay with that. In a couple of weeks I might wear a blazer with no tie as outerwear to the office just to ease into it. Oh, and the office runs cold so lots of Shetlands ;).

SailBoats, Whales, & Guatemala?


I picked up a new surcingle belt and the design is not the most typical. Generally you will find surcingle belts embroidered with nautical themes, preppy animals, or preppy sports themes. None of these things are bad, I wear them myself, but sometimes you want something a little different. Cue the belt.


I loved this Guatemalan design with dogs (link here) the moment I saw it. I posted it in on one of my Instagram stories and I got a ton of questions about it so I knew I was not alone in my admiration. I thought that this belt would be a great way to add some color to my outfits. I knew that it would look great with olive chinos as well as the standard khaki/blue OCBD combo. Along with adding color I thought it was a nice way to break up my standard look and add a little bit of individuality into the mix.

I got this belt at Leather Man on the Eliza B site (see here). In my opinion it is a steal at $42. Leather Man is my de facto place to get belts. If this belt does not do it for you they have you covered as they have plenty of others.