I've recently been in need of shirts. A few where shrunk and some are showing there age. After a discussion with my alterations tailor, I discovered that they actually do MTM and bespoke clothing. There pricing scheme is fair for MTM shirts, at about +-$70. That is only about $3 more than the English shirts I import because I like the french cuffs and bright colored stripes. I have been wanting to try some club collared shirts and collarless shirts. Well club collared shirts are hard to find Off the Rack and because of that a rarity. Since, these are MTM I get to try it out. Now, I already have one in a red and blue double stripe so, I am familiar with what works for me and how to wear it.
How to do it, they are like any other collar so, wear them that way. Big, round headed gentlemen should wear straight, long, more pointed collars. Thin, long headed gents should wear short, rounder, and more spread collars. They can be worn dressed up or casual, formal or sporty, and even without a jacket. I personally don't go jacket-less unless engaged in sports or wearing a something to cover my sleeves.
For me, I think I'll go with 2 different ones. I'll try a contrast collar one and a spread collar like the one Merkin is wearing with the bowler.
Here are plenty of examples:
Photo Credit: I have no idea where these were borrowed from, a few are from 2 Japanese blogs don't remember which ones, and the Richard Merkin photos are from the London Lounge and Ask Andy forums. If they are yours and you want them down shoot me an email at orange gentleman dot gmail dot com.