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Disclaimer: Reviving old thread...no apologies.

I've done this multiple times this fall, with one variation. Instead of limiting the layering to OCBD over OCBD, I've used a traditional-fit BB OCBD as an "undershirt" to be worn under a viyella shirt, a Pendleton/Filson wool shirt, a cotton flannel shirt, or another OCBD. The combination is kind of weird when getting dressed, having to tuck in two shirt tails. But instead of being affected, the look becomes very natural as the day goes on. The OCBD collar supports the collar of the overshirt and allows that collar to stand away from the throat. Kinda ascot-y, but not that precious. I can't really describe it, but it does look good.

For example, a typical kit might be white BB trad-fit OCBD, Bill's Fullerton red plaid cotton flannel buttondown, LLB khakis, merino wool casual socks, and a pair of blucher mocs or lace-up moc-toe boots. Throw in a Barbour Beaufort jacket or a corduroy sportcoat if you have to run around town. That outfit will hunt from now until spring.

In terms of warmth, I find that the combination, especially with a viyella shirt, is very comfortably (and surprisingly) warm around the house. Also, it is much lighter and more comfortable than wearing a sweater.

It's practical, functional, and looks good. What's not to love?
 
^^...and a timely resurrection, for sure.
During colder weather, I frequently layer a Pendleton wool Board or camp shirt over a BB or RPL woven cotton OCBD. I've also done this with Woolrich wool shirts. However, I cannot recall ever layering a cotton OCBD over a second cotton OCBD.
 
I usually stick to a flannel or wool shirt worn open or partly buttoned over an OCBD. It's a classic casual look and a bit leasier affected, in my mind at least. More "site boss" and less "trust fund."
 
I was just thinking about this last night. Double collars were the height of affectation when I was in high school, though I do appreciate the look of a rugby worn over an oxford. As has already been stated, an oxford with a chamois for a shirt jacket is a great look, one I grew up with.

The key, it seems to me, is that you have to vary the collars. Buttondown (or turtleneck) on the inner layer, regular on the outer layer.
 
So I read this thread after realizing getting dressed this morning. I was a touch chilly in just my flannel and decided to give it a shot, tell me what you think. Admittedly it's not an OCBD or rugby over an OCBD but I think it works?

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^ I don't think it works, personally. Patch-anything is hard to pull off. Patch flannel, which is much rarer than patch madras, makes enough of a statement on its own. Wearing it in an unconventional way makes it more so. On top of that, you're wearing it with a tie. It's too much.
 
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